5708-19-0

Basic information

• Product Name: (S)-(-)-3-CYCLOHEXENECARBOXYLIC ACID
• Synonyms: (S)-(-)-3-CYCLOHEXENECARBOXYLIC ACID;(1S)-cyclohex-3-ene-1-carboxylic acid;(S)-Cyclohex-3-enecarboxylic acid;(S)-3-Cyclohexene-1-carboxylic Acid;(S)-(?)-1,2,3,6-Tetrahydrobenzoic acid;(1S)-3-Cyclohexene-1-carboxylic acid;(S)-(-)-3-Cyclohexene-1-carboxylic Acid
• CAS NO: 5708-19-0
• Molecular Formula: C₇H₁₀O₂
• Molecular Weight: 126.15
• EINECS: 1592732-453-0
• Product Categories: Edoxaban
• Mol File: 5708-19-0.mol

Chemical Properties

• Melting Point: 19°C(lit.)
• Boiling Point: 118°C/6mmHg(lit.)
• Flash Point: 109.903 °C
• Appearance: /
• Density: 1.126 g/cm³
• Refractive Index: 1.4780 to 1.4820
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 4.67±0.20(Predicted)
• CAS DataBase Reference: (S)-(-)-3-CYCLOHEXENECARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-3-CYCLOHEXENECARBOXYLIC ACID(5708-19-0)
• EPA Substance Registry System: (S)-(-)-3-CYCLOHEXENECARBOXYLIC ACID(5708-19-0)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8 / PGIII
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 5708-19-0(Hazardous Substances Data)

Usage

Uses

(S)-(-)-3-Cyclohexenecarboxylic acid is used as an organic synthesis intermediate for the preparation of various chemical compounds. It is particularly useful in the development of pharmaceuticals, where it can be employed to create novel drug candidates with potential therapeutic applications.
Used in Pharmaceutical Industry:
(S)-(-)-3-Cyclohexenecarboxylic acid is used as a pharmaceutical intermediate for the synthesis of N-[(1R,2S,5S)-2-[(5-chloroindol-2-yl)carbonyl]amino-5-(dimethylcarbamoyl)cyclohexyl]-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxamide hydrochloride. (S)-(-)-3-Cyclohexenecarboxylic acid is a potent and orally active direct inhibitor of factor Xa, which plays a crucial role in the coagulation cascade. Inhibiting factor Xa can help in the treatment of various thrombotic disorders, such as deep vein thrombosis and pulmonary embolism.
Additionally, (S)-(-)-3-Cyclohexenecarboxylic acid can be used in laboratory research and development processes, where it may contribute to the discovery of new chemical entities with potential applications in various fields, including but not limited to, pharmaceuticals, agrochemicals, and materials science.

Synthesis

54.94 g of cyclohex-3-ene-1(S)-carboxylic acid (R)-(+)-methylbenzylamine salt and 18.2 volumes of H2O were charged to a flask at 20-25°C and stirred. To the mixture obtained further 6.7 volumes of H2O and 10 volumes of EtOAc were added. The mixture obtained was stirred for 15 min, the phases were separated and the organic layer was discarded. The aqueous layer was treated with 10 volumes of MTBE and 2.5 equivalents of 6M HCI were added slowly. The mixture obtained was stirred and two layers were formed, separated and the aqueous layer was extracted with MTBE. The organic layers obtained were combined and washed with aqueous, 30percent NaCl solution. The organic phase obtained was dried over Na2S04, filtered, and from the filtrate obtained solvent was removed in vacuo. Cyclohex-3-ene-1(S)-carboxylic acid in the form of a clear oil was obtained. Yield: 26.13 g (93.3percent of theory).

Upstream product

• 4771-80-6 1,2,5,6-tetrahydrobenzoic acid 
• 72581-32-9 cyclohex-3-enylmethanol 
• 5709-99-9 (R)-1-C-(1-Cyclohexen-5-yl)methanol 
• 102096-64-0 3-Cyclohexene-1-carboxylic acid (R)-pentalactone ester 
• 102096-60-6 (R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl acrylate 
• 106-99-0 buta-1,3-diene 
• 6493-77-2 methyl cyclohex-3-ene-1-carboxylate 
• 67976-82-3 (1S)-3-cyclohexene-1-carboxylic acid (R)-(+)-α-methylbenzylamine salt 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 1228540-49-5 Ethyl (R)-3-cyclohexene-1-carboxylate 
• 15111-56-5 ethyl-3-cyclohexene-1-carboxylate 
• 6493-77-2 (R)-(+)-methyl 3-cyclohexene-1-carboxylate 
• 5709-98-8 (R)-cyclohex-3-enecarboxylic acid 
• 116733-45-0 3-<(1R)-3-Cyclohexen-1-ylcarbonyl>-1,3-oxazolidin-2-one 

Downstream Products

• 5681-56-1 (S)-4-(Hydroxymethyl)cyclohexene 
• 123536-66-3 (1S,4S,5S)-4-iodo-6-oxabicyclo<3.2.1>octan-7-one 
• 163812-76-8 (1S,2S,4S)-4-(hydroxymethyl)-1-iodo-2-cyclohexanol 
• 349494-36-6 (1S,3R,4R)-3,4-dibromo-cyclohexanecarboxylic acid 
• 123453-95-2 (1S,5S)-(-)-5-(hydroxymethyl)-2-cyclohexen-1-ol 
• 349494-38-8 methyl c-4-bromo-c-3-hydroxy-r-1-cyclohexanecarboxylate 
• 349494-41-3 methyl (1S,3S,4S)-4-amino-3-hydroxy-1-cyclohexanecarboxylate 
• 349494-39-9 methyl (1S,3S,4R)-3-acetoxy-4-bromo-1-cyclohexanecarboxylate 
• 349494-40-2 methyl (1S,3S,4S)-3-acetoxy-4-azido-1-cyclohexanecarboxylate 
• 349494-42-4 methyl (1S,3S,4S)-4-(tert-butoxycarbonylamino)-3-hydroxy-1-cyclohexanecarboxylate 
• 163956-42-1 (1R,2S,4S)-4-(benzyloxymethyl)-1,2-epoxycyclohexane 
• 163812-78-0 (1R,4S)-4-(benzyloxymethyl)-2-cyclohexen-1-ol 
• 163812-77-9 (1R,2R,4S)-4-(benzyloxymethyl)-2-(phenylseleno)-1-cyclohexanol 
• 178945-61-4 (1'S,6'S)-2-(6'-benzyloxymethyl-2'-cyclohexenyl)ethanol 

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.

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 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.

Preparation method of S-3-cyclohexenecarboxylic acid and intermediates thereof, and intermediates of S-3-cyclohexenecarboxylic acid

The invention discloses a preparation method of S-3-cyclohexeneformic acid and intermediates thereof, and the intermediates thereof. The invention particularly discloses a preparation method of a compound as shown in a formula I which is described in the

Preparation method of edoxaban

The invention relates to a new preparation route and a new method for a p-toluenesulfonic acid edoxaban hydrate and intermediates thereof. The new method comprises the steps that a high-reactivity compound 109A4x is prepared; a compound 109C6x is prepared by using a new synthesizing method; new compounds 109E8-01, 109E9x and 109T7-01 are prepared; the p-toluenesulfonic acid edoxaban hydrate is prepared by using the intermediates. By using the new method and the new route, the reaction step of copious cooling is omitted, and dangerous elemental sulfur, high-risk n-butyllithium and high-risk azides are prevented from being used. In a word, by means of the method, the p-toluenesulfonic acid edoxaban hydrate and the key intermediates thereof are more easily and safely prepared at a lower coston an industrialization scale.

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

PROCESS FOR THE PREPARATION OF (1S,4S,5S)-4-BROMO-6-OXABICYCLO[3.2.1] OCTAN-7-ONE

The present invention relates to an improved and industrially advantageous process for the preparation of (1S, 4S, 5S) -4-bromo-6-oxabicyclo [3.2.1] octan-7-one represented by the following formula (I) which is a key intermediate in the synthesis of edoxaban, a compound that exhibits an inhibitory effect on activated blood coagulation factor X (also referred to as activated factor X or FXa), and is useful as a preventive and/or therapeutic drug for thrombotic diseases. The process includes reacting (1S) -cyclohex-3-ene-1-carboxylic acid of formula (II) with a brominating agent selected from the group consisting of N-bromosuccinimide or 1, 3-dibromo-5, 5-dimethylhydantoin in the presence of a base selected from calcium oxide or calcium hydroxide in a solvent selected from the group comprising of dichloromethane, toluene, tetrahydrofuran, ethy1 acetate, hexanes, cyclopentyl methyl ether (CPME) or a mixture thereof to get ( 1S, 4S, 5S) -4-bromo-6-oxabicyclo [3.2.1] octan-7-one of formula (I).

PROCESS FOR PRODUCING OPTICALLY ACTIVE CARBOXYLIC ACID

It has been demanded to provide a process for industrially producing an intermediate for a compound that exhibits an inhibitory effect on activated blood coagulation factor X and is useful as a preventive and/or therapeutic agent for thrombotic diseases. The present invention provides a process for producing the (R-α-phenylethylamine salt of (S)-3-cyclohexene-1-carboxylic acid, comprising reacting 3-cyclohexene-1-carboxylic acid and (R)-α-phenylethylamine using a mixed solvent of water and acetone or a mixed solvent of water and ethyl acetate as a solvent.

Enantiomerically pure amines

A compound of formula wherein PROT, PROT' and R have various meanings, processes for its production and production of intermediates in stereoisomerically pure form, and its use for the production of pharmaceutically active compounds.

Process for the preparation of pleuromutilins

A process for the preparation of a compound of formula in the form of a single stereoisomer, comprising deprotecting the amine group in an N-protected amino-hydroxy-cyclohexylsulfanyl-acetyl-mutilin of formula wherein R is an amine protecting group in the form of a single stereoisomer, and isolating a compound of formula I in the form of a single stereoisomer obtained from the reaction mixture; compounds obtainable by such processes, e.g. a compound of formula I in a crystalline form, or salts of a compound of formula I in crystalline form, and processes for the preparation of intermediates for the production of a compound of formula I.