Tag: M.W=200-250

Liu, Yu published the artcileGO-CNTs hybrids reinforced epoxy composites with porous structure as microwave absorbers, Related Products of quinuclidine, the publication is Composites Science and Technology (2020), 108450, database is CAplus.

Foam structures with epoxy as the matrix and both carbon nanotubes (CNTs) and their hybrids with graphene oxide (GO-CNTs) as absorbers were fabricated, and their microwave absorbing and electromagnetic properties were investigated in the frequency range of 1-18 GHz. The fillers and bubbles were uniformly distributed in the composites. The complex permittivity and elec. conductivity of the composites increased as the fillers’ content increasing. The best performance of the reflection loss (RL) can be obtained for a foam structure with 0.5 wt% GO-CNTs, which had a RL peak value of -20dB with a -10 dB range of 5.3 GHz (10.8-16.1 GHz). Multi-layered structures were also discussed in this work, a RL peak value of -40dB with a -10dB range of 7.1 GHz (9.9-17 GHz) had been obtained by combining two foam structures, which are 2 mm thick 0.5 wt% GO-CNTs/epoxy and 1 mm thick 2.0 wt% GO-CNTs/epoxy. Furthermore, the -10dB range can reach 11.5 GHz (6.5-18 GHz) when combining 2.6 mm thick 0.5 wt% GO-CNTs/epoxy and 1.3 mm thick 2.0 wt% GO-CNTs/epoxy.

Composites Science and Technology published new progress about 1761-71-3. 1761-71-3 belongs to quinuclidine, auxiliary class Ploymers, name is 4,4-Diaminodicyclohexyl methane, and the molecular formula is C13H26N2, Related Products of quinuclidine.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Heilbron, I. M. published the artcileUnion of aryl nuclei. II. Chloro-, bromo- and nitrofluorenones, Category: quinuclidine, the publication is Journal of the Chemical Society (1938), 113-16, database is CAplus.

By means of the Gomberg reaction, diazotized Me anthranilate (or a derivative) and a neutral aromatic liquid being used, nuclear-substituted biphenyl-2-carboxylic acids become readily available, from which the corresponding substituted fluorenones may be obtained quant. on ring closure. Me 4-chloroanthranilate and C₆H₆ thus give 25% of the Me ester, b₂₀ 180-90°, of 5-chlorodiphenyl-2-carboxylic acid (I), m. 152°; ring closure with H₂SO₄ gives 3-chlorofluorenone (II), yellow, m. 157°; 4-Cl isomer of I, m. 157°; 2-Cl isomer of II, m. 123°; 5-Br analog of I, m. 172°; 3-Br analog of II, m. 161°; the 4-isomers, m. 164°, and 150°, were likewise prepared 4-NO₂ analog of I, m. 173°; ring closure gives the 4-NO₂ analog of II, m. 219°. PhCl and PhBr give mixtures of the 2′- and 4′-Cl and Br derivatives, the separation of which was only partly successful. p-ClC₆H₄N₂Cl and PhMe give 4′-chloro-2-methylbiphenyl, b. 288-90°; oxidation gives 4′-chloro-biphenyl-2-carboxylic acid, m. 161°; ring closure gives the 2-Cl isomer of II.

Journal of the Chemical Society published new progress about 20029-52-1. 20029-52-1 belongs to quinuclidine, auxiliary class Carboxylic acid,Benzene, name is 4-Cyclohexylbenzoic acid, and the molecular formula is C13H16O2, Category: quinuclidine.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Barzic, A. I. published the artcileInterlayer dielectrics based on copolyimides containing non-coplanar alicyclic-units for multilevel high-speed electronics, Name: 4,4-Diaminodicyclohexyl methane, the publication is Polymer Testing (2020), 106704, database is CAplus.

A series of copolyimides (CPIs) containing non-coplanar alicyclic units combined with fluorinated or rigid aromatic monomer segments is synthesized. The solid film samples display an elevated heat resistance as their degradation started at temperatures around 415°C. Introduction into CPI backbone of bicyclic units, aromatic/aliphatic rings, angular bonds and/or low polarizable groups, determine the variation of the dielec. constant in the range 2.44-3.04 at 100 Hz. When using these CPIs as interlayer dielecs. (ILDs), it is revealed that resistance-capacitance delay is minimized (∼10-11 s) determining faster response of the device. Atomic force microscopy scans of CPI samples show distinct macromol. architectures, all containing nanopores with features depending on the chem. structure. Interfacial adhesion of investigated ILDs with copper wiring is highest for the samples lacking fluorine groups.

Polymer Testing published new progress about 1761-71-3. 1761-71-3 belongs to quinuclidine, auxiliary class Ploymers, name is 4,4-Diaminodicyclohexyl methane, and the molecular formula is C13H26N2, Name: 4,4-Diaminodicyclohexyl methane.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Yan, Lin published the artcileDiscovery of 3-arylpropionic acids as potent agonists of sphingosine-1-phosphate receptor-1 (S1P₁) with high selectivity against all other known S1P receptor subtypes, SDS of cas: 20029-52-1, the publication is Bioorganic & Medicinal Chemistry Letters (2006), 16(14), 3679-3683, database is CAplus and MEDLINE.

A series of 3-arylpropionic acids were synthesized as S1P₁ receptor agonists. Structure-activity relationship studies on the pendant Ph ring revealed several structural features offering selectivity of S1P₁ binding against S1P_2-5. These highly selective S1P₁ agonists induced peripheral blood lymphocyte lowering in mice and one of them was found to be efficacious in a rat skin transplantation model, supporting that S1P₁ agonism is primarily responsible for the immunosuppressive efficacy observed in preclin. animal models.

Bioorganic & Medicinal Chemistry Letters published new progress about 20029-52-1. 20029-52-1 belongs to quinuclidine, auxiliary class Carboxylic acid,Benzene, name is 4-Cyclohexylbenzoic acid, and the molecular formula is C13H10O2, SDS of cas: 20029-52-1.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

v. Braun, Julius published the artcileSyntheses in the bi- and terphenyl series. II, SDS of cas: 20029-52-1, the publication is Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1933), 1471-83, database is CAplus.

cf. C. A. 21, 2470. The attachment of the p-PhC₆H₄CH₂ group (I) to N and S is strikingly less firm than that of PhCH₂ (C. A. 18, 1830). To determine what influence the lengthening of the chain by another Ph residue to p-(p-PhC₆H₄)C₆H₄ (II) and hydrogenating 1 or 2 aromatic residues in I and II would have on the firmness of attachment of these groups, the following compounds have been prepared (all substituents in the p-position): C₆H₁₁Ph (III), C₆H₁₁C₆H₄CH₂X (X = Cl or Br) (IV), PhC₆H₄Ph (V), PhC₆H₄C₆H₄CH₂X (VI), C₆H₄C₆H₄Ph (VII), C₆H₁₁C₆H₄C₆H₄CH₂X (VIII), C₆H₁₁C₆H₁₀Ph (IX), C₆H₁₁C₆H₄C₆H₄CH₂X (X). p-Cyclohexylbenzaldehyde (XI) was obtained in small yield in 3 ways: (1) III, AlCl₃ and CuCl in benzene treated 15 hrs. with CO + HCl gave 14-16% XI, b₁₂ 160° (semicarbazone, m. 220°; oxime, m. 88°; aniline condensation product (XII), m. 122°; acetone condensation product, faintly yellow, m. 77°). With alkali (Cannizzaro) XI gives p-cyclohexyl-benzoic acid, m. 198° and p-cyclohexylbenzyl alc., b₁₂ 162° m. 41° also obtained easily from the chloride (IV, below) by treatment with AcOH-KOH and alk. saponification of the resulting acetate, b₁₂ 184°, m. 47°. (2) III with ClCOCO₂Et gives 30% of the ester C₆H₁₁C₅H₄CO-CO₂Et, thick yellow oil, b₁₂ 215-25°; the free acid (48% yield), m. 111° gives with PhNH₂ 50% XII which yields 6% XI (based on the III used). (3) III 3 mols.) allowed to stand 12 hrs. with 1 mol. anhydrous chloral and 0.25 mol. AlCl₃ gives 23% (based on the chloral) of the addition product C₆H₁₁C₆H₄CH(OH)CCl₃, thick yellow oil, b₁₆ 215°, which is quite smoothly converted into XI by boiling saturated K₂CO₃. The most striking property of XI is its extraordinarily pleasant citral-like odor, which it loses on acetalization; the di-Et acetal b₁₃ 181°. Ph₂, dry trioxymethylene and ZnCl₂, treated in the cold with HCl gas, give about 20% p-PhC₆H₄CH₂Cl, b_0.3 130°, m. 68°, and 12% 4,4′-bis(chloromethyl)biphenyl, m. 136°, b₁₂ 235°; the latter with hot aqueous alc. KCN gives the faintly yellowish dicyanide, m. 184°, with BzH the dibenzal derivative, decomposing 256°, and with hot HCl in sealed tubes at 130° biphenyl-4,4′-diacetic acid, m. 270-3° (di-Et ester, b_0.5 204-6°, m. 55°). Under the same conditions III gives 50% p-chloromethylhexahydrobiphenyl (IV, X = Cl), a viscous liquid oxidized by hot 30% HNO₃ in sealed tubes to p-C₆H₄(CO₂H)₂ and converted by short treatment with NHEt₂ into the compound C₆H₁₁C₆H₄CH₂NEt₂, b_0.1. 125° (methiodide, m. 186°). The mixture of cis- and trans-p-C₆H₁₁C₆H₁₀OH obtained by condensing C₆H₁₁OH with PhOH and hydrogenating the resulting C₆H₁₁C₆H₄OH yields quantitatively with 66% HBr in sealed tubes at 120° a mixture of the cis- and trans-bromides, b₁₄ 150-5°, which with AlCl₃ in C₆H₆-CS₂ yields cyclohexylcyclohexene, b₁₄ 110°, a mixture, b_0.5 130-50°, of much m-C₆H₁₁C₆H₁₀Ph with a little IX (as shown by dehydrogenation with Se at 300° to m-C₆H₄Ph₂ and 15% V), and a compound p-(m-C₆H₁₁C₆H₁₀)₂C₆H₄, m. 145°, which gives pure p-C₆H₄(CO₂H)₂ with HNO₃ and is dehydrogenated by Se to an isomer, m. 232°, of quinquephenyl. By treating p-cyclohexylcyclohexanone in the usual way with PhMgBr, boiling the product with 20% H₂SO₄, brominating the resulting decahydroterphenyl (XIII), b₁₈ 225-30°, m. 97-8°, and heating the product at 180° under 6 mm. is obtained 70% hexahydroterphenyl (VII), which m. 85° and is dehydrogenated to V by Se. p-BrC₆H₄Ph is conveniently prepared in a similar manner: p-C₆H₄Br₂ is treated with Mg activated with I and cyclohexanone and the product is boiled with 20% H₂SO₄, giving a little octahydroterphenyl, C₆H₉C₆H₄C₆H₉, m. 110° (which is readily hydrogenated to p-C₆H₄(C₆H₁₁)₂, m. 101°), and tetrahydro-p-bromobiphenyl, C₆H₉C₆H₄Br, b₁₄ 175-80°, m. 73°, which, brominated as above and heated in vacuo, yields pure p-BrC₆H₄Ph, m. 89°. This with Mg and cyclohexanone yields tetrahydroterphenyl which, however, cannot be completely freed of the carbinol even by boiling with H₂SO₄ and is therefore treated in ether with HCl gas to replace the OH group by Cl, and HCl is split off with pyridine; the hydrocarbon, m. 146-8°, is now nearly pure and with Pd and H gives VII but in such poor yield that the method cannot compete with that described above for preparing VII. With Pd and H in acetone XIII gives a mixture of dodecahydroterphenyl (IX), m. 86°, and a liquid stereoisomer (XIV) b_0.2 144°, which rearranged practically completely into IX when heated 2 hrs. in CS₂ with 0.02 mol. AlCl₃ and, like IX, is smoothly dehydrogenated to V by Se. More energetic hydrogenation of XIII (with Ni and H at 200°) gives octadecahydroterphenyl (XV), also in 2 stereo-isomeric forms: crystals m. 162° and 55-7°, resp. (this is also true of all the less highly hydrogenated derivatives of V and even of V itself); neither of the isomers can be rearranged into the other with AlCl₃, however. Hexadecahydroterphenyl, prepared like XIII from p-cyclohexyl-cyclohexanone and C₆H₁₁MgBr, b₁₃ 190°, m. 111-13°, gives the 2 isomeric XV with Pd and H. Attempts to introduce the CH₂Cl group into V were entirely unsuccessful and VII did not give much better results with the isomeric IX and XIV the reaction was more satisfactory; XIV with trioxymethylene, ZnCl₂ and HCl gas and subsequent treatment with NHEt₂ gave the base C₂₃H₃₇N (less than 10%), b_0.4 185-90°. 4,4” -Dibromoterphenyl (85% from V in C₆H₃Cl₃ with 4 atoms Br and a little I), m. 312-13°; the mother liquors yield only little of the mono-Br compound (XVI) which could also not be obtained in any appreciable yield by using only 2 atoms Br. p-Cyclohexylcyclohexanone with p-C₆H₄Br₂ and Mg yields 45% 4-bromodecahydroterphenyl (XVII), b_0.3 180-90°, m. 97-8°, which, treated in the cold with 2 atoms Br and then at 160° with 8 more atoms Br until the evolution of HBr ceases and distilled in vacuo, gives pure 4-bromoterphenyl (XVI), m. 230-2°; the mother liquors contain bromohexahydroterphenyl, m. 148°. Along with XVII is formed a little eicosahydroquinquephenyl, C₆H₄(C₆H₈-C₆H₁₁)₂, b_0.7 250°, m. 240-5°. XVI is as resistant as V to HCHO and HCl. 4-Methyldecahydroterphenyl, C₆H₁₁-C₆H₈C₆H₄Me (60% from p-MeC₆H₄MgBr and p-cyclohexylcyclohexanone), m. 108-10°, b0.7 165°, gives on hydrogenation a mixture of stereoisomeric 4-methyldodecahydroterphenyls, m. 82° and 36-8°, dehydrated by Se to 4-methylterphenyl, m. 206-8° (75% yield), which is oxidized by CrO₈ to terphenyl-4-carboxylic acid, m. 305°, and converted by adding 3/4 mol. Br dropwise to the C₆H₃Cl₃ solution into 4-bromomethylterphenyl (VI, X = Br), m. 210° (70% yield); this with NHEt₂ gives the base PhC₆H₄C₆H₄CH₂NEt₂, m. 133°.

Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen published new progress about 20029-52-1. 20029-52-1 belongs to quinuclidine, auxiliary class Carboxylic acid,Benzene, name is 4-Cyclohexylbenzoic acid, and the molecular formula is C8H15NO, SDS of cas: 20029-52-1.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Irizar, Pablo published the artcileSugar-derived bio-based resins as platforms for the development of multifunctional hybrids with potential application for stone conservation, Computed Properties of 1761-71-3, the publication is Materials Today Communications (2022), 103662, database is CAplus.

This research is focused on the design of a bio-based epoxy-silica hybrid, enriched with SiO₂ nanoparticles, to be used in stone conservation. For this purpose, isosorbide, a sugar derivative coming from renewable sources, was selected for the development of epoxy thermosets that were functionalized adding fixed amounts of silica-forming mixtures, to gain hybrid organic-inorganic networks. Fourier Transform IR (FTIR), Attenuated Total Reflection IR (ATR-FTIR) and Raman spectroscopies were exploited to follow the synthetic procedures, whereas the homogeneity of the networks was ascertained by SEM/energy-dispersive X-ray spectroscopy (SEM-EDS). The materials were investigated by thermogravimetric (TG-DTA), differential scanning calorimetry (DSC), dynamic mech. anal. (DMA) and contact angle measurements. Once the proper epoxy-silica product was identified, specifically synthesized nanoparticles were incorporated. The obtained nanocomposite showed excellent thermo-mech. (T_onset, T_g and T_α of 327, 55.9 and 70.1 °C, resp.) and hydrophobic (105°) properties making it a potential candidate for stone conservation.

Materials Today Communications published new progress about 1761-71-3. 1761-71-3 belongs to quinuclidine, auxiliary class Ploymers, name is 4,4-Diaminodicyclohexyl methane, and the molecular formula is C13H26N2, Computed Properties of 1761-71-3.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Schubert, Hermann published the artcileThe catalytic hydrogenation of aromatic-substituted imidazoles. V. (p-Biphenylyl)imidazoles, Product Details of C13H16O2, the publication is Journal fuer Praktische Chemie (Leipzig) (1961), 86-104, database is CAplus.

cf. CA 53, 15061c; 54, 7694b. The synthesis of a series of C-substituted (p-biphenylyl)imidazoles (I) is described. The catalytic hydrogenation of the I yields mixtures of the stereo- isomeric (4-bicyclohexylyl)imidazoles (II) from which only in a few cases homogeneous forms could be isolated. The II synthesized as mixtures of the stereoisomers as well as the homogeneous transforms were identical with the corresponding hydrogenation products. The biphenylyl group does not activate the imidazole system for a catalytic hydrogenation, p-PhC₆H₄CHO (III) (9.1 g.) in 500 cc. MeOH heated 1 hr. on the water bath with 5 g. HOCH₂CHO, 25 g. Cu(OAc)₂, and 200 cc. concentrated NH₄OH, the resulting white Cu salt (2.8 g.) suspended in H₂O and treated with H₂S, the filtrate allowed to stand, and the brown crystalline deposit sublimed in vacuo at 220° gave 2-(p-biphenylyl)imidazole (IV), needles, m. 249-50° (all m.ps. are corrected); picrate, yellow rods, m. 278-9° (EtOH). p-PhC₆H₄COCH₂OAc, Cu(OAc)₂, aqueous CH₂O, and concentrated NH₄OH gave similarly 67% 4(5)-(p-biphenylyl)imidazole (V), flakes, m. 221-2° (PhCl), which was also obtained from p-BrCH₂COC₆H₄Ph (VI) with HCONH₂; picrate, red-yellow needles, m. 198-201° (MeOH). VI (8.3 g.), 10 g. KOAc, and 200 cc. MeOH refluxed 2 hrs., filtered, diluted with MeOH to 1.2 1., heated 1 hr. on the water bath with 5.5 g. III, 200 cc. concentrated NH₄OH, and 15 g. Cu(OAc)₂ and filtered, and the resulting violet Cu salt (4.7 g.) decomposed in the usual manner with H₂S gave 2,4(5)-di(p-biphenylyl)imidazole (VII), needles, m. 302-3° (dioxane); picrate, deep yellow prisms, m. 290-5° (decomposition) (EtOH). p,p’-Diphenylbenzoin (VIII) (10.9 g.) and 250 cc. HCONH₂ refluxed 2 hrs. yielded 7.8 g. crude 4,5-di(p-biphenylyl)imidazole (IX). (p-PhC₆H₄CO)₂ (X) (1.05 g.), 0.2 g. urotropine (XI), and 3 g. NH₄OAc in 30 cc. AcOH heated 2 hrs. yielded 0.94 g. IX, needles, m. 291-2° (aqueous dioxane); picrate, gold-yellow leaflets, m. 263-5° (MeOH). VIII (7.4 g.) and 3.8 g. III in 800 cc. MeOH and 150 cc. HCONMe₂ refluxed and treated dropwise with 18 g. Cu(OAc)₂ in 108 cc. concentrated NH₄OH and filtered after 1 hr. and the resulting light brown Cu salt (6.5 g.) decomposed with H₂S in dilute boiling dioxane yielded 2,4,5-tri(p-biphenylyl)tmidazole (XII). X (3.62 g.) and 1.82 g. III heated 2 hrs. with 6 g. NH₄OAc in 50 cc. AcOH yielded 4.7 g. XII needles, m. 170-90° resolidifying at 190°; picrate, yellow crystal powder, m. 288-90° (EtOH). BzCH₂OH (4.1 g.) in 700 cc. MeOH heated 1 hr. on the water bath with 12 g. Cu(OAc)₂ and 200 cc. concentrated NH₄OH, and the resulting red-violet Cu salt (5.4 g.) decomposed with H₂S in 60% HCl-EtOH and poured into NH₄OH precipitated the 4(5)-Ph derivative (XIII) of V, prisms, m. 273-5° (dioxane); picrate, yellow needles, m. 256-64° (decomposition) (EtOH). III (3.7 g.), 4.2 g. Bz₂, and 12 g. NH₄-OAc in 100 cc. AcOH heated 2 hrs. gave 7 g. crude 4,5-di-Ph derivative (XIV) of I. Benzoin (4.24 g.) in 200 cc. MeOH heated 1 hr. on the water bath with 3.7 g. III, 9 g. Cu(OAc)₂, and 100 cc. concentrated NH₄OH, and the resulting, gray Cu salt (6 g.) decomposed in the usual manner with H₂S gave XIV, needles, m. 234-5° (dioxane or PhCl); picrate, yellow needles, m. 253-6° (EtOH). VI (5.5 g.) treated in the usual manner with KOAc, the mixture in 700 cc. MeOH heated 1 hr. on the water bath with 5 g. BzH, 18 g. Cu(OAc)₂. and 180 cc. concentrated NH₄OH, and the resulting Cu salt (4.2 g.) decomposed with H₂S gave 2-Ph derivative (XV) of V.0.5EtOH, needles, m, 222-4°; picrate-0.5EtOH, m. 233-9° (with elimination of the EtOH at 100°). VIII (14.5 g.) and 6 g. BzH in 1 1. MeOH and 250 cc. HCONMe₃ refluxed treated dropwise with 20 g.Cu(OAc)₂ in 360 cc. concentrated NH₄OH, and heated 1 hr., and the resultlng Cu salt (5.8 g.) decomposed with H₂S in 60% refluxing dioxane and cooled gave 2-Ph derivative (XVI) of IX, yellowish prisms. X (4.5 g.), 1.3 g. BzH, 7.5 g. NH₄OAc, and 60 cc. AcOH heated 2 hrs. yielded 5.3 g. (crude) XVI which recrystallized from EtOH gave XVI.0.5EtOH; picrate-0.5EtOH, yellow needles, m. 247-9° with transitions and intermediate melting at 150 and 205-30°. p-PhC₆H₄CO₂H (XVII) in AcOH hydrogenated over PtO₂ yielded 90% 4-bicyclohexylcarboxylic acid (XVIII), m. 72-94° (80% AcOH). Will in C₆H₆ treated with SOCl₂ yielded 90% acid chloride, b₁₈ 176-8°, which with CH₂N₂ yielded 4-bicyclohexylyl diazomethyl ketone (XIX), pale yellow needles, m. 68-92° (petr. ether). XIX in AcOH treated with KOAc gave 73% 4-bicyclohexylyl acetoxymethyl ketone (XX), needles, m. 78-82° (EtOH). XX (1 g.) in 25 cc. 50% EtOH heated 2 hrs. with 2 cc. concentrated H₂SO₄, cooled, and diluted with H₂O gave 70% HOCH₂ analog of XX, needles, m. 92-9° (petr. ether). XX ( 10.6 g.) in 400 cc. MeOH, 18 g. Cu(OAc)₂, 10 cc. aqueous CH₂O, and 200 cc. concentrated NH₃ heated 1 hr. on the water bath, and the resulting sand-colored Cu salt (10 g.) decomposed with H₂S yielded 6 g. (crude) 4(5)-(4-bicyclohexylyl)imidazole (XXI), m. 134-45° (PhCl); picrate, golden-yellow needles or flakes, m. 192-8° (EtOH). XVIII with CH₂N₂ gave 85% Me ester (XXII) of XVIII, b₁₄ 16970°. p-PhC₆H4CO₂Et (10 g.), m. 53-5°, in 200 cc. absolute EtOH and 10 cc. AcOH hydrogenated 12 hrs. over 5 g. PtO₂ (added in 3 portions of 1, 2, and 2 g.) yielded 80-90% Et ester of XVIII, b₁₈ 176-8°. XXII (26.9 g.) in 50 cc. dry Et₂O added slowly dropwise to 6 g. powd. Na in 300 cc. dry Et₂O with stirring, refluxed 8 hrs., decomposed carefully with dilute H₂SO₄, and worked up in the usual manner yielded 10 g. 4,4′-dicyclohexyldodecahydrobenzoin (XXIII), prisms, m. 128-42°; the Et₂O solution from the run deposited on standing colorless crystals, m. 228-44° (decomposition) (dioxane). XXIII (3.9 g.) in 70% AcOH oxidized with Cu(OAc)₂ during 2.5 hrs. gave 3.1 g. 4,4′-dicyclohexyldodecahydrobenzil (XXIV), yellow needles, m. 134-42 (dioxane); 2,4-dinitrophenylhydrazone, yellow needles, m. 190-205° (dioxane-EtOH). XXIII (3,9 g.), 70 cc. HCONH₂, and 30 cc. PhNO₂ refluxed 2 hrs., concentrated in vacuo, and added with stirring to concentrated NH₄OH gave 2.5 g. (crude) 4,5-di(4-bicyclohexylyl)imidazole (XXV), needles, m, 258-63° (PhCl). XXIV (1.8 g.) and 0.5 g. XI heated 2 hrs. with 3 g. NH₄OAc in 30 cc. AcOH yielded 0.9 g. XXV, needles, m. 257-62° (PhCl); picrate, yellow prisms, m. 235-42° (EtOH). XVIII refluxed 8 hrs. with SOCl₂ and then hydrolyzed gave trans-bicyclohexyl-4carboxylic acid (XXVI). trans-4-Phenylcyelohexanecarboxylic acid (XXVII) hydrogenated in AcOH over PtO₂ yielded XXVI, leaflets, m. 161-2° (pert. ether). XVII (5 g.) in 250 cc. AcOH hydrogenated 4.5 hrs. over 5 g. PtO₂ (added in 3 portions) gave 3.5 g. 4-cyclohexylbenzoic acid (XXVIII), m. 195-8°, and 0.7 g. mixture of XXVIII and trans-4-phenylcyclohexanecarboxylic acid, m. 166-9°. XXVI (15 g.) treated at room temperature with 100 cc. SOCl₂ and evaporated in vacuo, the residue dissolved in 150 cc. dry Et₂O and added dropwise to CH₂N₂-Et₂O, and the Et₂O evaporated after 3 hrs. yielded 7.7 g. 4(5)-trans-(4-bicyclohexylyl) diazomethyl ketone (XXIX), yellow-green leaflets, m. 98-100° (Et₂O). XXIX (7 g.) and 2 g. KOAc in 150 cc. AcOH kept 2 days at room temperature and poured into iced H₂O yielded 4.6 g. acetoxymethyl ketone analog (XXX) of XXIX, needles, m. 81.5-2.5° (EtOH). XXX (4 g.) in 200 cc. McOH, 70 cc. concentrated NH₄OH, 3.5 cc. 35% aqueous CH₂O, and 7 g. Cu(OAc)₂ heated 1 hr. on the water bath, and the crude Cu salt in 60% EtOH treated with H₂S, filtered, and evaporated yielded 0.95 g. trans-XXI, rhombs, m. 146-7° (C₆H₆); picrate, golden-yellow needles, m. 197.5-8.5° (EtOH). XXVII (20 g.) in 100 cc. Et₂O treated 2 days at room temperature with 70 cc. SOCl₂ gave 12.2 g. acid chloride which with CH₂N₂ yielded 7.5 g. trans-4-phenylcyclohexyl diazomethyl ketone (XXXI), green-yellow needles, m. 89-91° (decomposition) (Et₂O). XXXI (7 g.) gave in the usual manner 5.5 g. acetoxymethyl ketone analog (XXXII) of XXXI, needles, m. 74-5° (EtOH). XXXII (5 g.) in 200 cc. MeOH, 4 cc. CH₂O, 70 cc. concentrated NH₄OH, and 8 g. Cu(OAc)₂ gave in the usual manner 1.7 g. 4(5)-trans-(4-phenylcyclohexyl)imidazole (XXXIII), needles, m. 176-7° (aqueous EtOH); picrate, yellow needles, m. 202-3° (EtOH). XXVIII (20 g.) and 50 cc. SOCl₂ refluxed 1 hr. and evaporated, and the residue treated with CH₂N₂-Et₂O yielded 18.5 g. p-cyclohexylphenyl diazomethyl ketone (XXXIV), yellow leaflets, m. 105-7° (decomposition). XXXIV (18 g.) added in portions to 100 cc. AcOH heated 1 hr. with 2 g. KOAc, cooled, and added with stirring to iced H₂O gave 16 g. acetoxymethyl ketone analog (XXXV), needles, m. 80-1° (EtOH). XXXV (15 g.) in 400 cc. MeOH, 12 cc. 35% aqueous CH₂O, 250 cc. concentrated NH₄OH, and 15 g. Cu(OAc)₂ gave in the usual manner 8 g. 4(5)-(pcyclohexylphenyl)imidazole (XXXVI), needles, m. 173-4°; picrate, hydrate, golden-yellow needles, m. 85-95° (aqueous EtOH), m. 174-5.5° (after drying in vacuo). XXVI (35 g.) esterified with CH₂N₂, the Me ester in 90 cc. dry Et₂O added dropwise during 0.5 hr. to 8 g. powd. Na in 100 cc. dry Et₂O, stirred 10 hrs., stirred into iced H₂O and Et₂O, the aqueous phase extracted with Et₂O, and the combined Et₂O solutions worked up gave 8.5 g. trans,trans-4,4′-dicyclohexyldodecahydrobenzoin (XXXVII), leaflets, m. 146-7° (iso-Am₂O); 2,4-dinitrophenylhydrazone, brown-red needles, m. 227-8° (EtOH).XXXVII(3.5 g.), 1 g. Cu(OAc)₂, and 70% AcOH heated 1 hr., filtered, and poured into H₂O precipitated 2.6 g. trans,trans4,4′-dicyclohexyldodecahydrobenzil (XXXVIII), leaflets m. 143-4° (C₆H₆ or dioxane); 2,4-dinitrophenylhydrazone, yellow needles, m. 201-5° (EtOH). XXXVII(3g.), 20cc. HCONH₂, and 10 cc. PhNO₂ refluxed 2 hrs. and evaporated gave 0.9 g. trans-XXV, m. 265-6° (aqueous dioxane). XXXVIII (2 g.), 25 cc. AcOH, 3 g. NH₄OAc, and 1 g., XI heated 2 hrs., cooled, filtered, added with stirring to concentrated NH₄OH, and filtered yielded 1.4 g. trans-XXV, m. 265-6° (PhCl); picrate, yellow leaflets, m. 239-42° (EtOH). XXVII (30 g.) esterified with CH₂N₂ and then treated in the usual manner with 8 g. trans,trans-4,4’diphenyldodecahydrobenzoin (XXXIX), needles, m. 136-7.5° (iso-Am₂O). XXXIX (3 g.), 1 g. Cu(OAc)₂, and 70% AcOH refluxed 1 hr., filtered, and poured into H₂O precipitated 2.5 g. trans,trans-4,4′-diphenyldodecahydrobenzil (XL), deep yellow needles, m. 159-62° (C₆H₆ or dioxane). XXXIX (3 g.) and 150 cc. HCONH₂ refluxed 2 hrs. gave 0.7 g. 4,5-bis(trans-4-phenylcyelohexyl)imidazole (XLI), needles, m. 249- 50° (PhCl). XL (2 g.), 40 cc. AcOH, 3.5 g. NH₄OAc, and 1.4 g. XI heated 2 hrs. gave 1.1 g. XLI, needles, m. 249-50° (PhCl); picrate, yellow needles, m. 242-4° (EtOH). XXVIII treated with CH₂N₂-Et₂O gave 90% Me ester, leaflets, m. 47-8° (MeOH); a 30-g. portion condensed in the usual manner with 7 g. Na sand in dry Et₂O, and the resulting crude acyloin (2 g.) oxidized in 70% AcOH with 1 g. Cu(OAc)₂ gave 0.95 g. 4,4′-dicyclohexylbenzil, yellow-green crystals, m. 164.5-66° (dioxane). XXXIII (1 g.) in 50 cc. AcOH and 50 cc. 50% H₂SO₄ hydrogenated 2 hrs. at 21°/764 mm. over 1.2 g. PtO₂, filtered, and added with stirring and cooling to concentrated NH₄OH gave trans-XXI, m. 146-7°. XLI (1 g.) gave similarly trans-XXV, needles, m. 265-6° (PhCl). V (4 g.) in 75 cc. AcOH and 75 cc. 50% H₂SO₄ hydrogenated 3 hrs. at 20°/764 mm. over 2 g. PtO₂ gave 2 g. XXXVI, m. 170-4° (C₆H₆). XXXI (3 g.) in 100 cc. absolute EtOH hydrogenated 5 hrs. at 160°/100 atm. over 5 g. Ni-Mg oxalate catalyst and worked up, and the sirupy product treated with pieric acid gave 3.8 g. picrate of XXXVI. By similar hydrogenation in AcOH with and without added H₂SO₄ over PtO₂ were prepared the following compounds (m.p., m.p. of picrate, starting material, and g. amount used, cc. amount AcOH used, g. amount PtO₂ used, and hydrogenation time in hrs. given): 2-(4-bicyclohexylyl)imidazole, 145-210° (dioxane), 190-218°, IV, 0.5, 50, 0.5, 23; XXI, 130-45° (EtOH), 190-8°, V, 0.5, 50 (and 20 cc. 50% H₂SO₄), 1, 1; 2,4(5)-di(4-bicyclohexylyl)imidazole, 150-210° (EtOH), 130-210°, VII, 0.5, 100, 0.5, 15; XXV, 259-63° (and 230-58°) (EtOH),208-10° (and 235-42°), IX, 0.25, 75 (and 30 cc. 50% H₂SO₄), -, 4; 2,4,5-tri(4-bicyclohexylyl)imidazole, 110° (EtOH), -, XII, 0.25, 50, 0.25, 12; 2-(4-bicyclohexylyl)4(5)-cyclohexylimidazole, 160-70° (and 173-4°) (Me₂CO), -, XIII, 0.5, 50, 0.5, 6; 2-cyclohexyl-4(5)-(4-bicyclohex-ylyl)imidazole, 209-17° (and 224-6°) (EtOH), 190-8°, XV, 0.3, 50, 0.5, 9; 2-(4-bicyclohexylyl)-4,5-dicyclohexylimidazole, 185-98° (and 200-200.5°) (dioxane), -, XIV, 1-100, 0.5, 8; 2-cyclohexyl-4,5-di(4-bicyclohexylyl)imidazole, 95-104° (EtOH), -, XVI, 0.5, 50, 0.5, 20.

Journal fuer Praktische Chemie (Leipzig) published new progress about 20029-52-1. 20029-52-1 belongs to quinuclidine, auxiliary class Carboxylic acid,Benzene, name is 4-Cyclohexylbenzoic acid, and the molecular formula is C13H16O2, Product Details of C13H16O2.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Choi, Doo Li published the artcileInhibition of cellular proliferation and induction of apoptosis in human lung adenocarcinoma A549 cells by T-type calcium channel antagonist, Recommanded Product: 4-Cyclohexylbenzoic acid, the publication is Bioorganic & Medicinal Chemistry Letters (2014), 24(6), 1565-1570, database is CAplus and MEDLINE.

The anti-proliferative and apoptotic activities of new T-type calcium channel antagonist, 6e (BK10040) on human lung adenocarcinoma A549 cells were investigated. The MTT assay results indicated that BK10040 was cytotoxic against human lung adenocarcinoma (A549) and pancreatic cancer (MiaPaCa2) cells in a dose-dependent manner with IC₅₀ of 2.25 and 0.93 μM, resp., which is 2-fold more potent than lead compound KYS05090 despite of its decreased T-type calcium channel blockade. As a mode of action for cytotoxic effect of BK10040 on lung cancer (A549) cells, this cancer cell death was found to have the typical features of apoptosis, as evidenced by the accumulation of pos. cells for annexin V. In addition, BK10040 triggered the activations of caspases 3 and 9, and the cleavages of poly (ADP-ribose) polymerase (PARP). Moreover, the treatment with z-VAD-fmk (a broad spectrum caspase inhibitor) significantly prevented BK10040-induced apoptosis. Based on these results, BK10040 may be used as a potential therapeutic agent for human lung cancer via the potent apoptotic activity.

Bioorganic & Medicinal Chemistry Letters published new progress about 20029-52-1. 20029-52-1 belongs to quinuclidine, auxiliary class Carboxylic acid,Benzene, name is 4-Cyclohexylbenzoic acid, and the molecular formula is C13H16O2, Recommanded Product: 4-Cyclohexylbenzoic acid.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Ganesh, Thota published the artcileDevelopment of second generation EP2 antagonists with high selectivity, SDS of cas: 20029-52-1, the publication is European Journal of Medicinal Chemistry (2014), 521-535, database is CAplus and MEDLINE.

EP2 receptor has emerged as an important biol. target for therapeutic intervention. In particular, it has been shown to exacerbate disease progression of a variety of CNS and peripheral diseases. Deletion of the EP2 receptor in mouse models recapitulates several features of the COX-2 inhibition, thus presenting a new avenue for anti-inflammatory therapy which could bypass some of the adverse side effects observed by the COX-2 inhibition therapy. We have recently reported a cinnamic amide class of EP2 antagonists with high potency, but these compounds exhibited a moderate selectivity against prostanoid receptor DP1. Moreover they possess acrylamide moiety in the structure, which may result in liver toxicity over longer period of use in a chronic disease model. Thus, we now developed second generation indoleamide compounds devoid of the acrylamide functionality and that possess high potency and improved (>1000-fold) selectivity to EP2 over other prostanoid receptors.

European Journal of Medicinal Chemistry published new progress about 20029-52-1. 20029-52-1 belongs to quinuclidine, auxiliary class Carboxylic acid,Benzene, name is 4-Cyclohexylbenzoic acid, and the molecular formula is C13H16O2, SDS of cas: 20029-52-1.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Weis, Erik published the artcileIr^III-Catalyzed Selective ortho-Monoiodination of Benzoic Acids with Unbiased C-H Bonds, Safety of 4-Cyclohexylbenzoic acid, the publication is Chemistry – A European Journal (2020), 26(45), 10185-10190, database is CAplus and MEDLINE.

An iridium-catalyzed selective ortho-monoiodination of benzoic acids with two equivalent C-H bonds was presented. A wide range of electron-rich and electron-poor substrates underwent the reaction under mild conditions, with >20:1 mono/di selectivity. Importantly, the C-H iodination occurred selectively ortho to the carboxylic acid moiety in substrates bearing competing coordinating directing groups. The reaction was performed at room temperature and no inert atm. or exclusion of moisture was required. Mechanistic investigations revealed a substrate-dependent reversible C-H activation/protodemetalation step, a substrate-dependent turnover-limiting step and the crucial role of the AgI additive in the deactivation of the iodination product towards further reaction.

Chemistry – A European Journal published new progress about 20029-52-1. 20029-52-1 belongs to quinuclidine, auxiliary class Carboxylic acid,Benzene, name is 4-Cyclohexylbenzoic acid, and the molecular formula is C18H28B2O4, Safety of 4-Cyclohexylbenzoic acid.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider