5709-98-8

Basic information

• Product Name: (R)-(+)-3-CYCLOHEXENECARBOXYLIC ACID
• Synonyms: (R)-Cyclohex-3-enecarboxylic acid;(R)-(+)-1,2,3,6-Tetrahydrobenzoic acid;(1R)-cyclohex-3-ene-1-carboxylic acid;(R)-cyclohex-3-ene-1-carboxylicacid;(R)-(+)-3-CYCLOHEXENECARBOXYLIC ACID;(1R)-3-Cyclohexene-1-carboxylic acid;(R)-3-Cyclohexene-1-carboxylic acid;(R)-3-Cyclohexene-1β-carboxylic acid
• CAS NO: 5709-98-8
• Molecular Formula: C₇H₁₀O₂
• Molecular Weight: 126.15
• Product Categories: Chiral Reagents;Chiral Compound
• Mol File: 5709-98-8.mol

Chemical Properties

• Boiling Point: 241.7 °C at 760 mmHg
• Flash Point: 109.9 °C
• Appearance: /
• Density: 1.126 g/cm³
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform, Methanol
• PKA: 4.67±0.20(Predicted)
• CAS DataBase Reference: (R)-(+)-3-CYCLOHEXENECARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-3-CYCLOHEXENECARBOXYLIC ACID(5709-98-8)
• EPA Substance Registry System: (R)-(+)-3-CYCLOHEXENECARBOXYLIC ACID(5709-98-8)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• Hazardous Substances Data: 5709-98-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(+)-3-CYCLOHEXENECARBOXYLIC ACID is used as an intermediate in the synthesis of various pharmaceutical compounds. One of its key applications is in the production of Leustroducsin B (LSN-B), a novel colony-stimulating factor (CSF) inducer. LSN-B is isolated from Streptomyces platensis and has potential applications in the treatment of various diseases and conditions related to the immune system.
As an intermediate in the synthesis of Leustroducsin B, (R)-(+)-3-CYCLOHEXENECARBOXYLIC ACID plays a crucial role in the development of new drugs and therapies. Its unique chemical structure allows for further functionalization and modification, enabling the creation of more complex and effective pharmaceutical compounds.

Upstream product

• 6493-77-2 (R)-(+)-methyl 3-cyclohexene-1-carboxylate 
• 19914-76-2 (1S-cis)-6-Chlorcarbonyl-3-cyclohexen-1-carbonsaeure-methylester 
• 935-79-5 cis-1,2,3,6-tetrahydrophthalic anhydride 
• 4771-80-6 1,2,5,6-tetrahydrobenzoic acid 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 136030-00-7 (1R,2S)-1-Amino-2-indanol 
• 1352834-06-0 cyclohex-3-ene-1-carboxylic acid (S)-1-phenylethanamine salt 
• 4841-84-3 dimethyl cis-1,2,3,6-tetrahydrophthalate 
• 31139-02-3 (1R,6S)-6-methoxycarbonyl-3-cyclohexene-1-carboxylic acid 
• 943144-69-2 C₁₇H₁₉NO₃ 
• 6493-77-2 methyl cyclohex-3-ene-1-carboxylate 
• 119944-89-7 (2S)-N-(acryloyl)bornane-10,2-sultam 
• 106-99-0 buta-1,3-diene 
• 143347-67-5 (R)-Cyclohex-3-enecarboxylic acid (S)-1-methyl-2,5-dioxo-pyrrolidin-3-yl ester 

Downstream Products

• 5709-99-9 (R)-1-C-(1-Cyclohexen-5-yl)methanol 
• 54911-89-6 (1R,5R)-methyl-5-hydroxycyclohex-3-enecarboxylate 
• 127943-95-7 methyl (1R,3R)-3-(tert-butyldimethylsilyloxy)cyclohex-4-ene-1-carboxylate 
• 1026073-45-9 methyl (1R,3R,4R,5S)-3-(tert-butyldimethylsilyloxy)-4-hydroxy-5-methylcyclohexane-1-carboxylate 
• 1339943-40-6 C₅₆H₇₆O₁₈Si 
• 1339943-42-8 C₅₀H₆₂O₁₈ 
• 1350636-90-6 N-(cyclohex-3-en-1(R)-yl)-2,2,2-trifluoro-acetamide 
• 1350753-51-3 ethyl cyclohex-3-enyl-1(R)-carbamate 
• 1350636-87-1 (R)-(3-cyclohexenyl)carbamic acid tert-butyl ester 
• 1350636-89-3 {(1R,2R,4R)-4-[(tert-butoxycarbonyl)amino]-2-hydroxycyclohexyl}phenyl thioformate 
• 1350734-45-0 {(1S,2S,5S)-5-[(tert-butoxycarbonyl)-amino]-2-hydroxy-cyclohexyl} benzenecarbothioate 
• 1350767-92-8 3-cyclohexene-1(R)-amine hydrochloride 
• 1350636-92-8 {(1R,2R,4R)-4-[(2,2,2-trifluoro-acetyl)-amino]-2-hydroxy-cyclohexyl} benzene-carbothioate 
• 1350753-45-5 2-(cyclohex-3-en-1(R)-yl)-isoindole-1,3-dione 

Relevant articles and documents

Asymmetric Synthesis of Optically Active 3-Cyclohexene-1-carboxylic Acid Utilizing Lactic Ester as a Chiral Auxiliary in the Diastereoselective Diels–Alder Reaction

The optically active 3-cyclohexene-1-carboxylic acid was synthesized through a TiCl4-catalyzed diastereoselective Diels–Alder reaction utilizing lactic acid ester as a chiral auxiliary, which can be removed by washing with H2O. The (S)- and (R)-isomers were both derived from easily available ethyl l-lactate.

Preparation method of edoxaban tosylate and isomers thereof

The invention discloses a preparation method of edoxaban tosylate and isomers thereof. By taking a compound (I) and a compound (II) as starting materials, the method can be used to prepare any one ofhigh-purity edoxaban tosylate (1S, 2R, 4S), edoxaban tosylate enantiomers (1R, 2S, 4R), edoxaban tosylate epimers (1R, 2R, 4S) and edoxaban tosylate epimers (1S, 2S, 4R). Effective guarantee is provided for process research and quality control of the edoxaban tosylate bulk drug and related preparations, the preparation method is suitable for commercialization, the produced edoxaban tosylate bulk drug is high in purity and has great significance and practical value, and the production of the edoxaban tosylate bulk drug and the control of drug quality are facilitated.

Kinetic Resolution of Nearly Symmetric 3-Cyclohexene-1-carboxylate Esters Using a Bacterial Carboxylesterase Identified by Genome Mining

A new bacterial carboxylesterase (CarEst3) was identified by genome mining and found to efficiently hydrolyze racemic methyl 3-cyclohexene-1-carboxylate (rac-CHCM) with a nearly symmetric structure for the synthesis of (S)-CHCM. CarEst3 displayed a high substrate tolerance and a stable catalytic performance. The enantioselective hydrolysis of 4.0 M (560 g·L-1) rac-CHCM was accomplished, yielding (S)-CHCM with a >99% ee, a substrate to catalyst ratio of 1400 g·g-1, and a space-time yield of 538 g·L-1·d-1.

Preparation method of (R)-3-cyclohexeneformic acid

The invention discloses a preparation method of (R)-3-cyclohexenecarboxylic acid, and belongs to the technical field of medical intermediates. The preparation method comprises the following steps: refluxing 3-cyclohexenecarboxylic acid and 0.5 eq(1S, 2S)-

An efficient stereoselective synthesis of six stereoisomers of 3, 4-diaminocyclohexane carboxamide as key intermediates for the synthesis of factor Xa inhibitors

An efficient stereoselective route for the preparation of six stereoisomers of tert-butyl ((1R, 2S, 5S)-2-amino-5-(dimethylcarbamoyl)cyclohexyl)carbamate 1 starting from simple 3-cyclohexene-1-carboxylic acid has been described. Stereochemistry of the tit

OPTICAL RESOLUTION METHOD FOR CARBOXYLIC ACID

PROBLEM TO BE SOLVED: To provide a method for optical resolution of carboxylic acid. SOLUTION: Provided is a method for optical resolution of carboxylic acid in which (S)-3-cyclohexene-1-carboxylic acid represented by the chemical structure of the left side in formula (II) is produced from 3-cyclohexene-1-carboxylic acid represented by formula (I) by using, as solvent, hydrous acetonitrile and/or hydrous 2-propanol, and, as optical resolution agent, (1R,2S)-1-amino-2-indanol represented by the chemical structure of the right side in Formula (II). SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

GLYCOMIMETIC-PEPTIDOMIMETIC INHIBITORS OF E-SELECTINS AND CXCR4 CHEMOKINE RECEPTORS

Compounds, compositions and methods are provided for treating cancer and inflammatory diseases, and for releasing cells such as stem cells (e.g., bone marrow progenitor cells) into circulating blood and enhancing retention of the cells in the blood. More specifically, glycomimetic-peptidomimetic compounds that inhibit both E-selectins and CXCR4 chemokine receptors are described.

Pre-organization of the core structure of E-selectin antagonists

A new class of N-acetyl-dglucosamine (GlcNAc) mimics for Eselectin antagonists was designed and synthesized. The mimic consists of a cyclohexane ring substituted with alkyl substituents adjacent to the linking position of the fucose moiety. Incorporation into E-selectin antagonists led to the test compounds 8 and the 2'-benzoylated analogues 21, which exhibit affinities in the low micromolar range. By using saturation transfer difference (STD)-NMR it could be shown that the increase in affinity does not result from an additional hydrophobic contact of the alkyl substituent with the target protein E-selectin, but rather from a steric effect stabilizing the antagonist in its bioactive conformation. The loss of affinity found for antagonists 10 and 35 containing a methyl substituent in a remote position (and therefore unable to support to the stabilization of the core) further supports this hypothesis. Finally, when a GlcNAc mimetic containing two methyl substituents (52 and 53) was used, in which one methyl was positioned adjacent to the fucose linking position and the other was in a remote position, the affinity was regained.

GLYCOMIMETIC COMPOUNDS AND METHODS TO INHIBIT INFECTION BY HIV

Compounds, compositions and methods are provided for use to inhibit infection by human immunodeficiency virus (HIV). More specifically, the present invention relates to glycomimetic compounds that inhibit HIV infection, and uses thereof.

Enantioselective synthesis of oseltamivir phosphate

The key steps in the enantioselective synthesis of Tamiflu include an asymmetric Diels-Alder reaction, Mitsunobu inversion using Fukuyama modified Weinreb reagent, carbamate directed epoxidation. Epoxide opening with trimethylsilyl azide furnished a 3:1 mixture of regioisomers that converged to afford the same aziridine. Attempted preparation of the unsaturated ester regioselectively using 2-iodoxybenzoic acid (IBX) following Nicolaou's protocol failed. The unsaturated ester was prepared by phenylselenylation followed by selenoxide elimination.