27338-44-9

Usage

Type of compound

Carboxylic acid

Structural features

a. Cyclohexene ring
b. Propionic acid functional group

Applications

a. Intermediate in pharmaceutical production
b. Intermediate in agrochemical production
c. Synthesis of perfumes and fragrances

Biological activities

a. Antimicrobial properties
b. Anti-inflammatory properties

Versatility

Valuable in various chemical and pharmaceutical applications

Upstream product

• 186581-53-3 diazomethane 
• 84189-13-9 cyclohexene-1-acetyl chloride 
• 27338-40-5 cyclohex-1-enylmethyl-malonic acid 
• 136425-21-3 2-(1-cyclohexenyl)ethyl methanesulfonate 
• 22690-21-7 1-bromo-1-bromomethylcyclohexane 
• 37677-17-1 1-bromomethylcyclohexene 
• 105-53-3 diethyl malonate 
• 74120-62-0 ethyl 3-(1'-hydroxycyclohexyl)propionate 
• 76925-79-6 1-<2-(carboethoxy)-ethynyl>cyclohexanol 
• 4845-04-9 1-cyclohexene-1-methanol 
• 18448-47-0 methyl cyclohex-1-ene-1-carboxylate 
• 67-63-0 isopropyl alcohol 
• 18294-87-6 1-cyclohexenylacetic acid 
• 65173-43-5 ethyl 3-(cyclohex-1-en-1-yl)propionate 

Downstream Products

• 197148-66-6 3-Cyclohex-1-enyl-propionic acid 2-thioxo-2H-pyridin-1-yl ester 
• 22516-18-3 3-(cyclohex-1-en-1-yl)propan-1-ol 
• 27338-46-1 Diazo-1-(cyclohexen-1')yl-4-butanon-2 
• 749927-74-0 3-Cyclohex-1-enyl-thiopropionic acid S-pyridin-2-yl ester 
• 1488285-93-3 C₁₉H₂₃NO₂ 
• 389607-98-1 5-(1-cyclohexenyl)-pentanophenone N,N-dimethylhydrazone 
• 389607-99-2 5-(1-cyclohexenyl)-pentanophenone 
• 348135-81-9 1-(3-iodopropyl)cyclohex-1-ene 
• 63715-12-8 1-(3-mesyloxypropyl)-1-cyclohexene 
• 27338-45-0 (Cyclohexen-1')yl-3-propionsaeurechlorid 

Relevant academic research and scientific papers

Pyrrolidines and Piperidines by Ligand-Enabled Aza-Heck Cyclizations and Cascades of N-(Pentafluorobenzoyloxy)carbamates

Ligand-enabled aza-Heck cyclizations and cascades of N-(pentafluorobenzoyloxy)carbamates are described. These studies encompass the first examples of efficient non-biased 6-exo aza-Heck cyclizations. The methodology provides direct and flexible access to carbamate protected pyrrolidines and piperidines.

Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction

The preparation of unsaturated secondary lactams via the palladium-catalyzed cyclization of O-phenyl hydroxamates onto a pendent alkene is reported. This method provides rapid access to a broad range of lactams that are widely useful building blocks in alkaloid synthesis. Mechanistic studies support an aza-Heck-type pathway.

Diverse N-Heterocyclic Ring Systems via Aza-Heck Cyclizations of N-(Pentafluorobenzoyloxy)sulfonamides

Aza-Heck cyclizations initiated by oxidative addition of Pd0-catalysts into the N?O bond of N-(pentafluoro-benzoyloxy)sulfonamides are described. These studies, which encompass only the second class of aza-Heck reaction developed to date, provide direct access to diverse N-heterocyclic ring systems.

3-(cyclohex-1-en-1-yl)propionates and their use in perfume compositions

The present invention pertains to novel 3-(cyclohex-1-en-1-yl)propionates, the unexpected advantageous use thereof in enhancing, improving or modifying the fragrance of perfumes, colognes, toilet waters, fabric care products, personal products, and the like, and the unexpected advantageous use thereof in counteracting malodors.

Conformation-based restrictions and scaffold replacements in the design of hepatitis C virus polymerase inhibitors: Discovery of deleobuvir (BI 207127)

Conformational restrictions of flexible torsion angles were used to guide the identification of new chemotypes of HCV NS5B inhibitors. Sites for rigidification were based on an acquired conformational understanding of compound binding requirements and the roles of substituents in the free and bound states. Chemical bioisosteres of amide bonds were explored to improve cell-based potency. Examples are shown, including the design concept that led to the discovery of the phase III clinical candidate deleobuvir (BI 207127). The structure-based strategies employed have general utility in drug design.

Studies concerning the electrophilic amino-alkene cyclisation for the synthesis of bicyclic amines

The bromination of a series of cyclohexenyl substituted secondary amines 1a-i has been investigated using Br2, PHT and NBS. In the case of Br2 and NBS the secondary amines preferentially undergo N-bromination. In contrast, PHT cleanly affords the products of alkene dibromination. In the case of Br2 the N-bromo species then give the products of alkene dibromination, albeit less efficiently. On subsequent treatment with K2CO3 these dibromides form the corresponding hexahydroindoles 2a-h and octahydroquinoline 2i. The presence of an N-substituent bearing a stereogenic centre (1h and 1i) was studied and the products 2h and 2i were isolated with no diastereoselectivity. When NBS was used a novel cyclisation, forming bromo-substituted octahydroindoles 9a,b and d, was observed. In relation to this sequence it was shown that these products were not intermediates in the former Br2/PHT processes and that the reaction only proceeded in the presence of the succinimide by-product of N-bromination.

Inhibitors of hepatitis C virus RNA-dependent RNA polymerase, and compositions and treatments using the same

The invention relates to compounds of the formula 1 and to pharmaceutically acceptable salts, solvates, prodrugs and metabolites thereof, wherein W, Z, R1 and R2, are as defined herein. The invention also relates to methods of treating Hepatitis C virus in mammals by administering the compounds of formula 1, and to pharmaceutical compositions for treating such disorders, which contain the compounds of formula 1. The invention also relates to methods of preparing the compounds of formula 1.

INHIBITORS OF HEPATITIS C VIRUS RNA-DEPENDENT RNA POLYMERASE, AND COMPOSITIONS AND TREATMENTS USING THE SAME

The invention relates to compounds of the formula (I) and to pharmaceutically acceptable salts, solvates, prodrugs and metabolites thereof, wherein W, Z, R1and R2, are as defined herein. The invention also relates to methods of treating Hepatitis C virus in mammals by administering the compounds of formula (I), and to pharmaceutical compositions for treating such disorders, which contain the compounds of formula (I). The invention also relates to methods of preparing the compounds of formula (I).

Stereo- and regioselectivity of cyclization reactions in conformationally restricted epoxy ketones: Evaluation of C- versus O-alkylation process

The intramolecular addition reaction of metal enolates of ketones to oxiranes has been applied to a series of epoxy ketones derived from cyclohexene oxide. γ-Hydroxy ketones (γ-HKs, C-alkylation products) or hydroxy enol ethers (HEEs, O-alkylation products) are obtained, depending on the nature of the cyclic transition state in each case involved and the application of the Fu?rst-Plattner rule. The formation of HEEs by reaction of the same epoxy ketones under acid conditions is also described. In some cases, regioconvergent or chemoselective processes are conveniently obtained.