Heterocyclic Building Blocks-Quinuclidine

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: (5aS,10bR)-2-(2,4,6-Trichlorophenyl)-4,5a,6,10b-tetrahydro-2H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-11-ium tetrafluoroborate, is researched, Molecular C18H13BCl3F4N3O, CAS is 1214711-48-4, about A photoisomerization-coupled asymmetric Stetter reaction: application to the total synthesis of three diastereomers of (-)-cephalimysin A, the main research direction is photoisomerization Stetter reaction total synthesis cephalimysin enantioselective synthesis; Aspergillus fumigatus cephalimysin preparation total synthesis; Mugil cephalus Gray mullet mushroom fungus cephalimysin preparation.Application In Synthesis of (5aS,10bR)-2-(2,4,6-Trichlorophenyl)-4,5a,6,10b-tetrahydro-2H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-11-ium tetrafluoroborate.

The total synthesis of 8-epi-cephalimysin A, 8,9-epi-cephalimysin A and 9-epi-(-)-cephalimysin A is described. This catalytic enantioselective synthesis takes advantage of a novel tandem photoisomerization/Stetter reaction. The approach provides rapid access to the desired spirofuranone lactam core in good yield and excellent enantioselectivity. A late stage oxidation strategy allows for flexible access to three of the four diastereomers of cephalimysin A. Access to the epimers provides further support for the correction of the initially proposed relative stereochem. of cephalimysin A. The title compounds thus formed included 8-epi-cephalimycin A (I) and related substances, (5S,8R,9R)-8-Benzoyl-2-(3E)-3-hexen-1-yl-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione cephalimysin A. The synthesis of the target compounds was achieved using (5aR,10bS)-5a,10b-dihydro-2-(2,3,4,5,6-pentafluorophenyl)-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazinium, tetrafluoroborate(1-) as catalyst.

This literature about this compound(1214711-48-4)Application In Synthesis of (5aS,10bR)-2-(2,4,6-Trichlorophenyl)-4,5a,6,10b-tetrahydro-2H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-11-ium tetrafluoroboratehas given us a lot of inspiration, and I hope that the research on this compound((5aS,10bR)-2-(2,4,6-Trichlorophenyl)-4,5a,6,10b-tetrahydro-2H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-11-ium tetrafluoroborate) can be further advanced. Maybe we can get more compounds in a similar way.

Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Efficient access to chiral dihydrobenzoxazinones via Rh-catalyzed hydrogenation, published in 2019, which mentions a compound: 36620-11-8, mainly applied to benzoxazinone dihydro preparation enantioselective; benzoxazinylidene acetate ester hydrogenation rhodium catalyst, Application of 36620-11-8.

Rh/(S)-DTBM-SegPhos-catalyzed asym. hydrogenation of prochiral (Z)-2-(2-oxo-2H-benzo[b][1,4]oxazin-3(4H)-ylidene)acetate esters I (R = 6-F, 5-CH3, 7-Cl, etc.; R1 = CH3, C2H5) was successfully developed. A series of chiral dihydrobenzoxazinones (R)-II was prepared through efficient methodol. with good to excellent results (up to >99% conversion, 93% yield and >99% ee), which are important motifs in the biol. active mols.

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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Recommanded Product: (5aS,10bR)-2-(2,4,6-Trichlorophenyl)-4,5a,6,10b-tetrahydro-2H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-11-ium tetrafluoroborate. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: (5aS,10bR)-2-(2,4,6-Trichlorophenyl)-4,5a,6,10b-tetrahydro-2H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-11-ium tetrafluoroborate, is researched, Molecular C18H13BCl3F4N3O, CAS is 1214711-48-4, about Oxyanion Steering and CH-π Interactions as Key Elements in an N-Heterocyclic Carbene-Catalyzed [4 + 2] Cycloaddition. Author is Allen, Scott E.; Mahatthananchai, Jessada; Bode, Jeffrey W.; Kozlowski, Marisa C..

The N-heterocyclic carbene catalyzed [4 + 2] cycloaddition has been shown to give γ,δ-unsaturated δ-lactones in excellent enantio- and diastereoselectivity. However, preliminary computational studies of the geometry of the intermediate enolate rendered ambiguous both the origins of selectivity and the reaction pathway. Here, we show that a concerted, but highly asynchronous, Diels-Alder reaction occurs rather than the stepwise Michael-type or Claisen-type pathways. In addition, two crucial interactions are identified that enable high selectivity: an oxyanion-steering mechanism and a CH-π interaction. The calculations accurately predict the enantioselectivity of a number of N-heterocyclic carbene catalysts in the hetero-Diels-Alder reaction.

This literature about this compound(1214711-48-4)Recommanded Product: (5aS,10bR)-2-(2,4,6-Trichlorophenyl)-4,5a,6,10b-tetrahydro-2H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-11-ium tetrafluoroboratehas given us a lot of inspiration, and I hope that the research on this compound((5aS,10bR)-2-(2,4,6-Trichlorophenyl)-4,5a,6,10b-tetrahydro-2H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-11-ium tetrafluoroborate) can be further advanced. Maybe we can get more compounds in a similar way.

Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Application In Synthesis of Bis(norbornadiene)rhodium (I) tetrafluoroborate. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: Bis(norbornadiene)rhodium (I) tetrafluoroborate, is researched, Molecular C14H8BF4Rh, CAS is 36620-11-8, about (Z)-Selective Hydroboration of Terminal Alkynes Catalyzed by a PSP-Pincer Rhodium Complex.

A highly (Z)-selective hydroboration of terminal alkynes was achieved using a thioxanthene-based PSP-pincer Rh catalyst. This hydroboration exhibited good chemoselectivity toward alkynes over carbonyl compounds such as ketones and aldehydes. The mechanistic studies indicated the involvement of Rh-vinylidene intermediates, and the high (Z)-selectivity could be attributed to the rigid and electron-rich nature of the PSP-Rh catalyst.

This literature about this compound(36620-11-8)Application In Synthesis of Bis(norbornadiene)rhodium (I) tetrafluoroboratehas given us a lot of inspiration, and I hope that the research on this compound(Bis(norbornadiene)rhodium (I) tetrafluoroborate) can be further advanced. Maybe we can get more compounds in a similar way.

Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: (5aS,10bR)-2-(2,4,6-Trichlorophenyl)-4,5a,6,10b-tetrahydro-2H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-11-ium tetrafluoroborate, is researched, Molecular C18H13BCl3F4N3O, CAS is 1214711-48-4, about A photoisomerization-coupled asymmetric Stetter reaction: application to the total synthesis of three diastereomers of (-)-cephalimysin A, the main research direction is photoisomerization Stetter reaction total synthesis cephalimysin enantioselective synthesis; Aspergillus fumigatus cephalimysin preparation total synthesis; Mugil cephalus Gray mullet mushroom fungus cephalimysin preparation.Electric Literature of C18H13BCl3F4N3O.

The total synthesis of 8-epi-cephalimysin A, 8,9-epi-cephalimysin A and 9-epi-(-)-cephalimysin A is described. This catalytic enantioselective synthesis takes advantage of a novel tandem photoisomerization/Stetter reaction. The approach provides rapid access to the desired spirofuranone lactam core in good yield and excellent enantioselectivity. A late stage oxidation strategy allows for flexible access to three of the four diastereomers of cephalimysin A. Access to the epimers provides further support for the correction of the initially proposed relative stereochem. of cephalimysin A. The title compounds thus formed included 8-epi-cephalimycin A (I) and related substances, (5S,8R,9R)-8-Benzoyl-2-(3E)-3-hexen-1-yl-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione cephalimysin A. The synthesis of the target compounds was achieved using (5aR,10bS)-5a,10b-dihydro-2-(2,3,4,5,6-pentafluorophenyl)-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazinium, tetrafluoroborate(1-) as catalyst.

This literature about this compound(1214711-48-4)Electric Literature of C18H13BCl3F4N3Ohas given us a lot of inspiration, and I hope that the research on this compound((5aS,10bR)-2-(2,4,6-Trichlorophenyl)-4,5a,6,10b-tetrahydro-2H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-11-ium tetrafluoroborate) can be further advanced. Maybe we can get more compounds in a similar way.

Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Safety of (5aS,10bR)-2-(2,4,6-Trichlorophenyl)-4,5a,6,10b-tetrahydro-2H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-11-ium tetrafluoroborate. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: (5aS,10bR)-2-(2,4,6-Trichlorophenyl)-4,5a,6,10b-tetrahydro-2H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-11-ium tetrafluoroborate, is researched, Molecular C18H13BCl3F4N3O, CAS is 1214711-48-4, about Experimental and Computational Gas Phase Acidities of Conjugate Acids of Triazolylidene Carbenes: Rationalizing Subtle Electronic Effects.

In recent years, triazolylidene carbenes have come to the forefront as important organocatalysts for a wide range of reactions. The fundamental properties of these species, however, remain largely unknown. Herein, the gas phase acidities have been measured and calculated for a series of triazolium cations (the conjugate acids of the triazolylidene carbenes) that have not been heretofore examined in vacuo. The results are discussed in the context of these species as catalysts. We find correlations between the gas phase acidity and selectivity in two Umpolung reactions catalyzed by these species; such correlations are the first of their kind. We are able to use these linear correlations to improve reaction enantioselectivity. These results establish the possibility of using these thermochem. properties to predict reactivity in related transformations.

This literature about this compound(1214711-48-4)Safety of (5aS,10bR)-2-(2,4,6-Trichlorophenyl)-4,5a,6,10b-tetrahydro-2H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-11-ium tetrafluoroboratehas given us a lot of inspiration, and I hope that the research on this compound((5aS,10bR)-2-(2,4,6-Trichlorophenyl)-4,5a,6,10b-tetrahydro-2H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-11-ium tetrafluoroborate) can be further advanced. Maybe we can get more compounds in a similar way.

Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 36620-11-8, is researched, Molecular C14H8BF4Rh, about Facile access to functionalized chiral secondary benzylic boronic esters via catalytic asymmetric hydroboration, the main research direction is chiral secondary benzylic boronic ester preparation; stereoselective hydroboration regioselective allylic phosphonate rhodium catalyst.Application of 36620-11-8.

Allylic and homoallylic phosphonates bearing an aryl or heteroaryl substituent at the γ- or δ-position undergo rhodium-catalyzed asym. hydroboration by pinacolborane to give functionalized chiral secondary benzylic boronic esters in yields up to 86% and enantiomer ratios up to 99 : 1. Compared to minimally-functionalized terminal and 1,1-disubstituted vinyl arenes, there are relatively few reports of efficient catalytic asym. hydroboration (CAHB) of more highly functionalized internal alkenes. Phosphonate substrates bearing a variety of common heterocyclic ring systems, including furan, indole, pyrrole and thiophene derivatives, as well as those bearing basic nitrogen substituents (e.g., morpholine and pyrazine) are tolerated, although donor substituents positioned in close proximity of the alkene can influence the course of the reaction. Stereoisomeric (E)- and (Z)-substrates afford the same major enantiomer of the borated product. Deuterium-labeling studies reveal that rapid (Z)- to (E)-alkene isomerization accounts for the observed (E/Z)-stereoconvergence during CAHB. The synthetic utility of the chiral boronic ester products is illustrated by stereospecific C-B bond transformations including stereoretentive electrophile promoted 1,2-B-to-C migrations, stereoinvertive SE2 reactions of boron-ate complexes with electrophiles, and stereoretentive palladium- and rhodium-catalyzed cross-coupling protocols.

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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: Bis(norbornadiene)rhodium (I) tetrafluoroborate(SMILESS: [F-][B+3]([F-])([F-])[F-].C12=C3[Rh+]14567(C8=C5C9C6=C7C8C9)C%10=C4C2CC3%10,cas:36620-11-8) is researched.Reference of Bis(norbornadiene)rhodium (I) tetrafluoroborate. The article 《How Cationic Metalloligands Affect the Coordination of Lewis Basic Ligands in RhI Complexes》 in relation to this compound, is published in Organometallics. Let’s take a look at the latest research on this compound (cas:36620-11-8).

A series of RhI complexes featuring cationic diphosphinometal ligands (PMPn+) has been synthesized, and the effect of the dative RhI → Mn+ interactions on other ligands coordinated to the RhI center were studied. The Rh-CO bond strength in square pyramidal [(PMP)Rh(CO)X]n+-type complexes (X = Cl, H) is dominated by the charge of the metalloligand. Complex [(PZnP)Rh(CO)H](NTf2)2 (7) was evaluated for its competence in hydroformylation catalysis. Computational anal. of octahedral [(PMP)Rh(CO)2H]n+ model complexes revealed a strengthening of the Rh-CO bond trans to the metalloligand with increasing at. number of the metalloligand.

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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Reference of Bis(norbornadiene)rhodium (I) tetrafluoroborate. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: Bis(norbornadiene)rhodium (I) tetrafluoroborate, is researched, Molecular C14H8BF4Rh, CAS is 36620-11-8, about Rh(I)-Catalyzed enantioselective and scalable [4 + 2] cycloaddition of 1,3-dienes with dialkyl acetylenedicarboxylates. Author is Bao, Robert Li-Yuan; Yin, Junjie; Shi, Lei; Zheng, Limin.

An asym. intermol. [4 + 2] cycloaddition of 1,3-dienes with dialkyl acetylenedicarboxylates, which was catalyzed by a rhodium(I)-chiral phosphoramidite complex, was developed. This protocol provided a highly enantioselective access to prepare carbonyl substituted cyclohexa-1,4-dienes with up to 96% yield and >99% ee [e.g., di-Me acetylenedicarboxylate + (E)-1,3-nonadiene → I (96%, 99% ee)]. Notably, a cycloaddition on the 10 g scale gave the product in 92% yield and with 99% ee, which showed great potential for the scale-up synthesis of carbonyl substituted cyclohexa-1,4-dienes. In addition, oxidative aromatizations and hydrolysis of the products were also investigated.

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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 36620-11-8, is researched, SMILESS is [F-][B+3]([F-])([F-])[F-].C12=C3[Rh+]14567(C8=C5C9C6=C7C8C9)C%10=C4C2CC3%10, Molecular C14H8BF4RhJournal, Chinese Chemical Letters called Facile access to chiral 4-substituted chromanes through Rh-catalyzed asymmetric hydrogenation, Author is Tao, Lin; Zhao, Qingyang; Zhang, Xumu; Dong, Xiu-Qin, the main research direction is chromane preparation enantioselective; chromanylidene acetate asym hydrogenation rhodium catalyst.Category: quinuclidine.

Rh/ZhaoPhos-catalyzed asym. hydrogenation of a series of (E)-2-(chroman-4-ylidene)acetates I (R = H, Cl, F, MeO; R1 = CO2Me, CO2Et, CO2iPr) was successfully developed to prepare various chiral 4-substituted chromanes II with high yields and excellent enantioselectivities (up to 99% yield, 98% ee). Moreover, the gram-scale hydrogenation could be performed well in the presence of 0.02 mol% catalyst loading (TON = 5000) and the hydrogenation product II (R = H, R1 = CO2Et) was easily converted to access other important compounds, II (R = H, R1 = CO2H, CH2OH) which demonstrated the synthetic utility of this asym. catalytic methodol.

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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider