Day: November 21, 2022

O’Donnell, Michael published the artcile2-Chloro-4-tetrafluorophenoxypyrimidine: a versatile reagent for C-2 prior to C-4 functionalizations, Recommanded Product: 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, the publication is Tetrahedron Letters (2016), 57(17), 1882-1884, database is CAplus.

A novel synthetic route to 2,4-functionalized pyrimidines is reported. The approach uses 2-chloro-4-tetrafluorophenoxypyrimidine, that enables sequential palladium catalyzed functionalization at the pyrimidine C-2 position, followed by S_NAr displacement with diverse amines at C-4. The broad utility of this “C-2 then C-4” functionalization sequence has been demonstrated with a range of cross-coupling partners and amines.

Tetrahedron Letters published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C28H41N2P, Recommanded Product: 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine.

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

Ou, Shuo-jun published the artcileDetermination of seven kinds of alkylamines in food contact plastic materials by amidation coupled with high performance liquid chromatography-quadrupole time-of-flight mass spectrometer, Name: 4,4-Diaminodicyclohexyl methane, the publication is Fenxi Huaxue (2020), 48(3), 413-422, database is CAplus.

A high performance liquid chromatog.-quadrupole time-of-flight mass spectrometry (HPLC-Q-TOF/MS) method for determination of seven kinds of alkylamines was established. Samples were amidated with 0.4% benzyl chloroformate (Cbz-Cl) in acetonitrile-sodium carbonate solution (50:50, V/V). The amidated conditions, including concentration of sodium carbonate solution (1.5%, m/V), benzyl chloroformate ratio and amount of sodium chloride (1.5 g), were optimized by response surface methodol. Under the optimized chromatog. and mass spectrometer conditions, the data were collected with electrospray ionization (ESI) sources under pos. ion mode. The calibration curves of seven kinds of alkylamines showed good linearity in concentration range of 1.0-500μg/L(R² > 0.9957). The average recoveries were 82.0-108.0%, the limits of detection and quantification were 0.5-1.0μg/kg and 2.0-4.0μg/kg, resp., and the relative standard deviations (RSDs) were 3.5-6.8%. This method is efficient and easy to be operated, and has good sensitivity, high precision and accuracy in the determination of seven alkylamines in food contact plastic materials.

Fenxi Huaxue 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

Lukesh, John C. published the artcileVinblastine 20′ Amides: Synthetic Analogues That Maintain or Improve Potency and Simultaneously Overcome Pgp-Derived Efflux and Resistance, Application In Synthesis of 20029-52-1, the publication is Journal of Medicinal Chemistry (2017), 60(17), 7591-7604, database is CAplus and MEDLINE.

A series of 180 vinblastine 20′ amides were prepared in three steps from com. available starting materials, systematically exploring a typically inaccessible site in the mol. enlisting a powerful functionalization strategy. Clear structure-activity relationships and a structural model were developed in the studies which provided many such 20′ amides that exhibit substantial and some even remarkable enhancements in potency, many that exhibit further improvements in activity against a Pgp overexpressing resistant cancer cell line, and an important subset of the vinblastine analogs that display little or no differential in activity against a matched pair of vinblastine sensitive and resistant (Pgp overexpressing) cell lines. The improvements in potency directly correlated with target tubulin binding affinity, and the reduction in differential functional activity against the sensitive and Pgp overexpressing resistant cell lines was found to correlate directly with an impact on Pgp-derived efflux.

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, Application In Synthesis of 20029-52-1.

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

Zuo, Hanqi published the artcileEffect of structure on the properties of ambient-cured coating films prepared via a Michael addition reaction based on an acetoacetate-modified castor oil prepared by thiol-ene coupling, Recommanded Product: 4,4-Diaminodicyclohexyl methane, the publication is Progress in Organic Coatings (2019), 27-33, database is CAplus.

The Michael addition reaction was used to create ambient curable film materials based on an acetoacetate-modified castor oil, and a multifunctional alamine was prepared The thiol-ene coupling reaction could change the proportion of hydroxyl groups in the castor oil, thereby improving the crosslinking d. and mech. properties of the coating films. The acetoacetate-modified castor oil was achieved in two steps. First, the C=C bonds of castor oil were coupled using a thiol-ene coupling reaction, which has a high conversion rate and few byproducts. Second, acetoacetate-modified castor oil was prepared by a transesterification reaction between tert-Bu acetoacetate and modified castor oil. The acetoacetate-modified castor oil was characterized by NMR (NMR), Fourier transform IR spectroscopy (FTIR), gel permeation chromatog. (GPC) and viscosity measurements. Finally, coating films were prepared from the acetoacetate-modified castor oil and 4,4-diaminecyclohexylmethane via a Michael addition reaction at room temperature (25 °C). The mech. properties were noticeably improved compared to those of the unmodified castor oil film. The tensile properties increased from 0.68 MPa to 1.76 MPa, and the glass transition temperature (T_g) increased by approx. 30 °C.

Progress in Organic Coatings 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 C10H9NO4S, Recommanded Product: 4,4-Diaminodicyclohexyl methane.

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

Liu, Haitao published the artcileRobust and flexible transparent protective film fabricated with an ambient-curable hybrid resin, Recommanded Product: 4,4-Diaminodicyclohexyl methane, the publication is Journal of Coatings Technology and Research (2021), 18(4), 1065-1073, database is CAplus.

An ambient-curable hybrid resin (ACHR) terminated with trimethoxysilane functional groups, synthesized through a simple ring-opening reaction between 3-glycidyloxypropyltrimethoxysilane (KH560) and 4,4′-methylenebis (cyclohexylamine) (PACM), was applied to the surface of a transparent organic polymer to produce a robust, flexible, and transparent protective hybrid film, moisture cured at room temperature The structure, morphol., and optical, mech., and thermal properties of the obtained hybrid film were evaluated. The hybrid film allowed the transmittance of more than 87% of visible light (at 600 nm), maintaining almost the same high transparency as bare PET film. The unique flexible segments and rigid segments in the inorganic-organic hybrid structure of the film realized superior resistance to bending and scratching. The hybrid film-coated PET demonstrated excellent flexibility, with an extremely low bending radius, illustrated by wrapping around a 1-mm mandrel bar without cracking. In addition, the hybrid film exhibited superior pencil hardness (of 2H) and excellent wear durability, i.e., no scratching after being subjected to 200 abrasion cycles using #0000 steel wool under a 19.6 kPa load. The robust, flexible, and transparent protective film developed here, and its simple and efficient preparation method, should have extensive application prospects.

Journal of Coatings Technology and Research 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, Recommanded Product: 4,4-Diaminodicyclohexyl methane.

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

Kinaci, Emre published the artcileInfluence of epoxidized cardanol functionality and reactivity on network formation and properties, Computed Properties of 1761-71-3, the publication is Polymers (Basel, Switzerland) (2020), 12(9), 1956, database is CAplus and MEDLINE.

Cardanol is a renewable resource based on cashew nut shell liquid (CNSL), which consists of a phenol ring with a C15 long aliphatic side chain in the meta position with varying degrees of unsaturation Cardanol glycidyl ether was chem. modified to form side-chain epoxidized cardanol glycidyl ether (SCECGE) with an average epoxy functionality of 2.45 per mol. and was cured with petroleum-based epoxy hardeners, 4-4′-methylenebis(cyclohexanamine) and diethylenetriamine, and a cardanol-based amine hardener. For comparison, cardanol-based diphenol diepoxy resin, NC514 (Cardolite), and a petroleum-based epoxy resin, diglycidyl ether of bisphenol-A (DGEBA) were also evaluated. Chem. and thermomech. analyzes showed that for SCECGE resins, incomplete cure of the secondary epoxides led to reduced cross-link d., reduced thermal stability, and reduced elongation at break when compared with difunctional resins containing only primary epoxides. However, because of functionality greater than two, amine-cured SCECGE produced a T_g very similar to that of NC514 and thus could be useful in formulating epoxy with renewable cardanol content.

Polymers (Basel, Switzerland) 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

Kinaci, Emre published the artcileEpoxidation of cardanol’s terminal double bond, Quality Control of 1761-71-3, the publication is Polymers (Basel, Switzerland) (2020), 12(9), 2104, database is CAplus and MEDLINE.

In this investigation, the terminal double bonds of the side chain epoxidized cardanol glycidyl ether (SCECGE) mol. were further epoxidized in the presence of Oxone (potassium peroxomonosulfate) and fluorinated acetone. Regular methods for the double bond epoxidation are not effective on the terminal double bonds because of their reduced electronegativity with respect to internal double bonds. The terminal double bond functionality of the SCECGE was epoxidized to nearly 70%, increasing the epoxy functionality of SCECGE from 2.45 to 2.65 epoxies/mol. as measured using proton magnetic nuclear resonance (¹H-NMR). This modified material-side chain epoxidized cardanol glycidyl ether with terminal epoxies (TE-SCECGE)-was thermally cured with cycloaliphatic curing agent 4,4′-methylene bis(cyclohexanamine) (PACM) at stoichiometry, and the cured polymer properties, such as glass transition temperature (T_g) and tensile modulus, were compared with SCECGE resin cured with PACM. The T_g of the material was increased from 52 to 69°C as obtained via a dynamic mech. anal. (DMA) while the tensile modulus of the material increased from 0.88 to 1.24 GPa as a result of terminal double bond epoxidation In addition to highlighting the effects of dangling side groups in an epoxy network, this modest increase in T_g and modulus could be sufficient to significantly expand the potential uses of amine-cured cardanol-based epoxies for fiber reinforced composite applications.

Polymers (Basel, Switzerland) 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, Quality Control of 1761-71-3.

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

Rao, K. V. Raghavendra published the artcileTheoretical Study, Synthesis, and Reactivity of Five-Membered-Ring Acyl Sulfonium Cations, HPLC of Formula: 162515-68-6, the publication is European Journal of Organic Chemistry (2015), 2015(28), 6125-6129, database is CAplus.

The feasibility of the cyclization of γ-alkylthiobutyric acid derivatives to form previously unknown five-membered-ring acyl sulfonium cations was studied. Exptl. results were in good agreement with our DFT calculations that predicted such cyclizations to be easy if starting with acyl iodides and mixed anhydrides of triflic acid. Particularly efficient were the reactions of γ-alkylthiobutyryl fluorides with trimethylsilyl triflate in CDCl₃ solution, which led to cyclic acyl sulfonium triflates. In some cases, the observed acyl sulfonium salts were stable enough to be characterized by NMR spectroscopy. They were found to be both alkyl-transfer reagents and acylating agents. They react with amines to form amides. These findings lend some weight to our hypothesis that the acyl sulfonium derived from methionine may have played a major role in the prebiotic synthesis of the first peptides on the primitive Earth.

European Journal of Organic Chemistry published new progress about 162515-68-6. 162515-68-6 belongs to quinuclidine, auxiliary class Thiol,Carboxylic acid,Aliphatic cyclic hydrocarbon, name is 2-(1-(Mercaptomethyl)cyclopropyl)acetic acid, and the molecular formula is C6H10O2S, HPLC of Formula: 162515-68-6.

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

Xiao, Xueyang published the artcilePolymeric dual-modal imaging nanoprobe with two-photon aggregation-induced emission for fluorescence imaging and gadolinium-chelation for magnetic resonance imaging, Computed Properties of 1353016-70-2, the publication is Bioactive Materials (2023), 538-549, database is CAplus and MEDLINE.

Nanoprobes that offer both fluorescence imaging (FI) and magnetic resonance imaging (MRI) can provide supplementary information and hold synergistic advantages. However, synthesis of such dual-modality imaging probes that simultaneously exhibit tunability of functional groups, high stability, great biocompatibility and desired dual-modality imaging results remains challenging. In this study, we used an amphiphilic block polymer from (ethylene glycol) Me ether methacrylate (OEGMA) and N-(2-hydroxypropyl) methacrylamide (HPMA) derivatives as a carrier to conjugate a MR contrast agent, Gd-DOTA, and a two-photon fluorophore with an aggregation-induced emission (AIE) effect, TPBP, to construct a MR/two-photon fluorescence dual-modality contrast agent, Gd-DOTA-TPBP. Incorporation of gadolinium in the hydrophilic chain segment of the OEGMA-based carrier resulted in a high r¹ value for Gd-DOTA-TPBP, revealing a great MR imaging resolution The contrast agent specifically accumulated in the tumor region, allowing a long enhancement duration for vascular and tumor contrast-enhanced MR imaging. Meanwhile, coupling TPBP with AIE properties to the hydrophobic chain segment of the carrier not only improved its water solubility and reduced its cytotoxicity, but also significantly enhanced its imaging performance in an aqueous phase. Gd-DOTA-TPBP was also demonstrated to act as an excellent fluorescence probe for two-photon-excited bioimaging with higher resolution and greater sensitivity than MRI. Since high-resolution, complementary MRI/FI dual-modal images were acquired at both cellular and tissue levels in tumor-bearing mice after application of Gd-DOTA-TPBP, it has great potential in the early phase of disease diagnosis.

Bioactive Materials published new progress about 1353016-70-2. 1353016-70-2 belongs to quinuclidine, auxiliary class Other Aromatic Heterocyclic,Carboxylic acid,Amide,Inhibitor,Inhibitor, name is Dbco-acid, and the molecular formula is C14H31NO2, Computed Properties of 1353016-70-2.

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

Buu-Hoi published the artcileChemistry of cyclohexylbenzene, COA of Formula: C13H16O2, the publication is Bulletin de la Societe Chimique de France (1944), 127-36, database is CAplus.

Cyclohexylbenzene (I) is an excellent starting material for organic syntheses; its derivatives crystallize readily, are soluble in most organic solvents; they are often cleaved by AlCl₃ (II), forming cyclohexyl radicals. Condensation of 15 g. I with 10 g. phthalic anhydride in 150 cc. of benzene (III), wi h 20 g. of II under cooling, yields after decomposition with HCl 2-(p-cyclohexylbenzoyl)benzoic acid (IV), m. 179-80° (from petr. ether). Reduction of IV with Zn and NH₄OH gives 2-(p-cyclohexylbenzyl)benzoic acid, m. 137° (from III). I condensed with succinic anhydride in PhNO₂, with II, gives β-(p-cyclohexylbenzoyl)propionic acid (V), m. 134° (from III). Clemmensen-Martin reduction of V gives γ-(p-cyclohexylphenyl)butyric acid (VI), b₁₈ 240°, m. 47° (from III + petr. ether); its acid chloride (VII), b_3-4 185-90°, treated with NH₃ yields the acid amide of VI, m. 128° (from III). Reaction of 6 g. of VII with 5 g. of II in III yields 3 g. of 7-cyclohexyl-1-tetralone (VIII), b₂₁ 222-4° (semicarbazone, m. 270-1°) (decomposition), some α-tetralone, and I, the latter being formed from cyclohexyl radicals and III. Clemmensen-Martin reduction of VIII yields 7-cyclohexyl-1,2,3,4-tetrahydronaphthalene (IX), b₂₀ 192-5°. Dehydrogenation of IX with Se at 335-40° for 15 h. is a good method for preparing 2-C₁₀H₇Ph. Heating equimolar amounts of VIII and isatin with 3 mols. of KOH for 24 h. on the steam cone in a min. of alc. gives 2-cyclohexyl-12-aza-7-benzanthracenecarboxylic acid (decomposition on heating). The Grignard reagent prepared from 145 g. p-bromocyclohexylbenzene yields with 30 g. of (CH₂)₂O at -10° 50 g. of 2-(p-cyclohexylphenyl)ethanol (X), b₁₄ 190-5°; phenylurethane, m. 100°. Treating 50 g. of X in CHCl₃ with 28 g. PBr₃ yields 30 g. of 2-(p-cyclohexylphenyl)-1-bromoethane (XI), b₁₄ 188-90°. Addition of 27 g. of XI to 18 g. of Et malonate (XII) in 25 cc. of absolute alc. containing 2.3 g. of Na yields 20 g. of Et [2-(p-cyclohexylphenyl)ethyl]malonate (XIII), b₁₅ 245-8°, saponified to VI. Addition of 10 g. of XI to a solution of 10 g. of PhCH(CO₂Et)₂ in 50 cc. of xylene and 1 g. of Na yields Et (phenyl(2-p-cyclohexylphenyl)malonate, b_3-4 245-55°, saponified to α-phenyl-γ-(p-cyclohexylphenyl)butyric acid (XIV), b_2.5 260°, m. 134° (from III). The acid chloride (XV) of XIV treated with NH₃ yields the amide of XIV m. 106-7°. Reaction of XV with II and III gives 2-phenyl-7-cyclohexyl-1-tetralone (XVI), b_2.7 240-50°, some I, and 2-phenyltetralone. Clemmensen reduction of XVI gives 2-phenyl-7-cyclohexyl-1,2,3,4-tetrahydronaphthalene, b_0.7 190-200°, dehydrogenated by Se to 2,7-diphenylnaphthalene, m. 142-3° (from alc.). KCN with p-(chloromethyl)cyclohexylbenzene (XVII) in EtOH results in a mixture of p-cyclohexylbenzyl Et ether, b₁₃ 175-7°, and (p-cyclohexylphenyl)acetonitrile (XVIII), b₁₂ 189-92°, m. 38°. Condensation of XVIII with p-ONC₆H₄NMe₂ by KOH gives p-C₆H₁₁C₆H₄ C(CN):NC₆H₄NMe₂ (XIX), m. 124-5°, and C₆H₁₁C₆H₄C(CN):̈ONC₆H₄NMe₂, m. 197-8° (from AcOH). Acid hydrolysis of XIX gives some C₆H₁₁C₆H₄COCN, m. 50° (petr. ether), and alk. hydrolysis leads to p-cyclohexylbenzoic acid, m. 197° (from AcOH). Condensation of 5 g. of XVIII with 2.8 g. of BzH (EtONa) gives α-(p-cyclohexylphenyl)cinnamonitrile (XX), m. 117° (alc.), and with 2.5 g. of furfural yields α-(p-cyclohexylphenyl)-2-furanacrylonitrile, m. 64°. These nitriles could not be hydrolyzed. Condensation of XX with III and II yields I and a mixture of PhCH(CN)CHPh₂ and Ph₂C(CN)CH₂Ph, not further purified. Saponification of XVIII with KOH gives (p-cyclohexylphenyl)acetic acid; its acid chloride (XXI), b₃ 165-6°, upon treatment with NH₃ gives (p-cyclohexylphenyl)acetamide, m. 163° (from III). XXI in III treated with II yields I, desoxybenzoin, and some p-cyclohexyldesoxybenzoin, b₁₆ 260-70°, m. 103° (from alc.). If the condensation is carried out in PhNO₂, 45 g. p,p’-dicyclohexyldesoxybenzoin, b_1.6 250-60°, m. 146°, is obtained and no cleavage of the cyclohexyl radical occurs. Condensation of XVII (45 g.) with 32 g. iso-PrCOPh previously treated with 8.9 g. NaNH₂ (XXII) in 200 cc. of III yields 47 g. of p-C₆H₁₁C₆H₄CH₂CMe₂Bz (XXIII), b₂ 223-6°. By treatment with XXII cleavage of XXIII to C₆H₁₁C₆H₄CH₂CMe₂CONH₂ (XXIV), m. 125°, is effected. NaOBr degradation of XXIV leads to the isocyanate, b₂ 145-50°, which upon treatment with HCl gives C₆H₁₁C₆H₄CH₂CMe₂NH₂.HCl; free base, b₃ 157-9°, m. 45° (from petr. ether); picrate, m. 175°; Bz derivative, m. 135°. To 90 g. of XII in 120 g. absolute alc. and 11 g. of Na, 100 g. of XVII was added, yielding 100 g. of Et (p-cyclohexylphenylmethyl) malonate, b₁₃ 230-2°; saponification yields the substituted malonic acid, m. 163° (with loss of CO₂). On distilling the acid, β-(p-cyclohexylphenyl)propionic acid (XXV), b_15-16 225-30°, m. 125° (from III), is obtained; its acid chloride (XXVI), b_2.5 170-2°, treated with NH₃ yields the amide of XXV, m. 167°. Reaction of 15 g. of XXVI with 50 cc. of III, with II catalyst, yields 7 g. of 6-cyclohexyl-1-indanone (XXVII), b_13-14 203-5°, m. 87° (semicarbazone, m. 230°), and some I and 1-indanone. XXVII condensed with isatin, with KOH, gives 3-cyclohexyl-5-aza-6,7-benzofluorene-8-carboxylic acid, decarboxylating on heating to 3-cyclohexyl-5-aza-6,7-benzofluorene, b₂ 240-50°, m. 129° (from alc.); picrate, decompose below 200°. Clemmensen reduction of XXVII yields 6-cyclohexylindan, b₁₆ 174-6°. Cyclohexyl p-nitrobenzoate, b₂ 180°, m. 52° (from alc.), prepared by treating p-O₂NC₆H₄COCl with excess of cyclohexanol, shows remarkable properties against pneumococci and tubercle bacilli.

Bulletin de la Societe Chimique de France 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, COA of Formula: C13H16O2.

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