(S)-(-)-3-Cyclohexenecarboxylic acid

Base Information

• Chemical Name: (S)-(-)-3-Cyclohexenecarboxylic acid
• CAS No.: 5708-19-0
• Molecular Formula: C7H10O2
• Molecular Weight: 126.155
• Hs Code.: 2916200090
• European Community (EC) Number: 634-675-3
• Nikkaji Number: J761.975H
• Mol file: 5708-19-0.mol

Synonyms:5708-19-0;(S)-(-)-3-CYCLOHEXENECARBOXYLIC ACID;(1S)-cyclohex-3-ene-1-carboxylic acid;(S)-Cyclohex-3-enecarboxylic acid;(S)-3-Cyclohexene-1-carboxylic acid;(S)-(+)-3-Cyclohexenecarboxylic acid;(S)-(-)-Cyclohex-3-enecarboxylic acid;3-Cyclohexene-1-carboxylic acid, (1S)-;(S)-(-)-3-CYCLOHEXENE-1-CARBOXYLIC ACID;MFCD08275437;(S)-Cyclohex-3-enecarboxylicacid;SCHEMBL468425;VUSWCWPCANWBFG-ZCFIWIBFSA-N;AKOS006287439;(1S)-3-cyclohexene-1-carboxylic acid;AM10071;CS-T-13953;CS-W018428;AC-33550;AS-34197;C3236;FT-0774177;EN300-320966;(S)-(-)-1,2,3,6-TETRAHYDROBENZOIC ACID

Chemical Property of (S)-(-)-3-Cyclohexenecarboxylic acid

Chemical Property:

• Melting Point: 19°C(lit.)
• Refractive Index: 1.4780 to 1.4820
• Boiling Point: 241.726 °C at 760 mmHg
• PKA: 4.67±0.20(Predicted)
• Flash Point: 109.903 °C
• PSA: 37.30000
• Density: 1.126 g/cm³
• LogP: 1.42730
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 126.068079557
• Heavy Atom Count: 9
• Complexity: 138

Purity/Quality:

99% ^*data from raw suppliers

(S)-(-)-3-Cyclohexene-1-carboxylic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(CC=C1)C(=O)O
• Isomeric SMILES: C1C[C@@H](CC=C1)C(=O)O
• Uses: (S)-(-)-3-CYCLOHEXENECARBOXYLIC ACID can be used as organic synthesis intermediates and pharmaceutical intermediates, mainly used in laboratory research and development processes and chemical production processes. (S)-3-Cyclohexene-1-carboxylic Acid has been used as a reactant for the preparation 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, a potent and orally active direct inhibitor of factor Xa.

Technology Process of (S)-(-)-3-Cyclohexenecarboxylic acid

There total 31 articles about (S)-(-)-3-Cyclohexenecarboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

(1S)-3-cyclohexene-1-carboxylic acid (R)-(+)-α-methylbenzylamine salt (67976-82-3) → (1S)-3-cyclohexenecarboxylic acid (5708-19-0)

Guidance literature:

With hydrogenchloride; In water; ethyl acetate;

DOI:10.1016/j.bmc.2008.12.037

Reference yield: 99.0%

(R)-Cyclohex-3-enyl-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-methanone → (1S)-3-cyclohexenecarboxylic acid (5708-19-0)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 25 ℃; for 18h;

DOI:10.1002/hlca.19840670527

Reference yield: 97.0%

3-Cyclohexene-1-carboxylic acid (R)-pentalactone ester (102096-64-0) → (1S)-3-cyclohexenecarboxylic acid (5708-19-0)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water;

DOI:10.1016/S0040-4039(00)98627-1

upstream raw materials:

1,2,5,6-tetrahydrobenzoic acid

cyclohex-3-enylmethanol

(R)-1-C-(1-Cyclohexen-5-yl)methanol

(S)-4-(Hydroxymethyl)cyclohexene

Downstream raw materials:

carbamic acid, N-[(1R,2S,5S)-2-[[2-[(5-chloro-2-pyridinyl)amino]-2-oxoacetyl]amino]-5-[(dimethylamino)carbonyl]cyclohexyl]-1,1-dimethylethyl ester

edoxaban

{(1R,2R,4S)-2-[(tert-butoxycarbonyl)amino]-4-[(dimethylamino)carbonyl]cyclohexyl}methanesulfonate

N₁-(5-chloropyridin-2-yl)-N₂-{(1R,2R,4S)-4-(dimethylaminocarbonyl)-2-[(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carboxamido]cyclohexyl}oxalamide p-toluenesulfonic acid

Refernces

• 1、 -. "Preparation method of edoxaban tosylate and isomers thereof". Paragraph 0071-0074-0076. . Retrieved 2021/02/06.
• 2、 -. "Preparation method of S-3-cyclohexenecarboxylic acid and intermediates thereof, and intermediates of S-3-cyclohexenecarboxylic acid". Paragraph 0078; 0079; 0085-0087; 0088; 0092. . Retrieved 2020/05/01.