(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanecarboxylic acid

Base Information

• Chemical Name: (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanecarboxylic acid
• CAS No.: 16052-40-7
• Molecular Formula: C11H20 O2
• Molecular Weight: 184.279
• Hs Code.: 2916200090
• European Community (EC) Number: 240-199-3
• UNII: 19IQ88IBRI
• DSSTox Substance ID: DTXSID40884866
• Nikkaji Number: J342.464B
• Wikidata: Q27252101
• Mol file: 16052-40-7.mol

Synonyms:16052-40-7;(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanecarboxylic acid;(1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexanecarboxylic acid;L-menthol carboxylic acid;Cyclohexanecarboxylic acid, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-;(-)-Menthylformic acid;p-Menthane-3-carboxylic acid, (1R,3R,4S)-;UNII-19IQ88IBRI;(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexane-1-carboxylic acid;19IQ88IBRI;(1R,3R,4S)-p-menthane-3-carboxylic acid;EINECS 240-199-3;[1R-(1alpha,2beta,5alpha)]-2-(isopropyl)-5-methylcyclohexanecarboxylic acid;p-Menthane-3-carboxylic acid, (1R,3R,4S)-(-)-;(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexane-1-carboxylic acid;(1R-(1alpha,2beta,5alpha))-2-(Isopropyl)-5-methylcyclohexanecarboxylic acid;CYCLOHEXANECARBOXYLIC ACID, 5-METHYL-2-(1-METHYLETHYL)-, (1R-(1.ALPHA.,2.BETA.,5.ALPHA.))-;Cyclohexanecarboxylic acid, 5-methyl-2-(1-methylethyl)-, [1R-(1.alpha.,2.beta.,5.alpha.)]-;SCHEMBL1150651;(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanecarboxylicacid;DTXSID40884866;CS-B1297;(-)-(1R,3R,4S )-4-Isopropyl-1-methylcyclohexane-3-carboxylic acid;CX1223;MFCD00798812;AKOS016000241;AMY202003215;EN300-3086707;Q-201317;Q27252101;(1R)-5beta-Methyl-2alpha-(1-methylethyl)-1beta-cyclohexanecarboxylic acid;Cyclohexanecarboxylic acid, 5-methyl-2-(1-methylethyl)-, (1R-(1alpha,2beta,5alpha))-;71030-83-6

Chemical Property of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanecarboxylic acid

Chemical Property:

• Vapor Pressure: 0.00187mmHg at 25°C
• Boiling Point: 270.9°Cat760mmHg
• PKA: 5.19±0.31(Predicted)
• Flash Point: 131.8°C
• PSA: 37.30000
• Density: 0.965g/cm³
• LogP: 2.77940
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 184.146329876
• Heavy Atom Count: 13
• Complexity: 187

Purity/Quality:

99.9% ^*data from raw suppliers

(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(C(C1)C(=O)O)C(C)C
• Isomeric SMILES: C[C@@H]1CC[C@H]([C@@H](C1)C(=O)O)C(C)C

Technology Process of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanecarboxylic acid

There total 19 articles about (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanecarboxylic 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: 97.0%

(1R,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxaldehyde (80434-59-9,485843-44-5,796865-68-4) → (-)-(1R,3R,4S)-4-isopropyl-1-methylcyclohexane-3-carboxylic acid (16052-40-7)

Guidance literature:

With jones' reagent; In acetone; at 20 ℃; for 1h;

DOI:10.1021/ja037078a

Reference yield: 93.0%

carbon dioxide (124-38-9,18923-20-1) + (1R,2S,5R)-menthyl chloride (16052-42-9) → (-)-(1R,3R,4S)-4-isopropyl-1-methylcyclohexane-3-carboxylic acid (16052-40-7)

Guidance literature:

(1R,2S,5R)-menthyl chloride; With iodine; magnesium; ethylene dibromide; at 70 - 75 ℃; for 4h; Inert atmosphere; Autoclave;

carbon dioxide; at 85 - 90 ℃; for 7.5h;

With hydrogenchloride; In water; Temperature;

Reference yield: 91.0%

C11H19N (1217664-77-1,439924-29-5) → (-)-(1R,3R,4S)-4-isopropyl-1-methylcyclohexane-3-carboxylic acid (16052-40-7)

Guidance literature:

With potassium hydroxide; In tert-butyl alcohol; Reflux;

upstream raw materials:

5-Pentyl-2-((1R)-3c-methyl-6t-isopropyl-cyclohexyl-(1r))-resorcin

acetone

(1R,2S,5R)-menthyl chloride

carbon dioxide

Downstream raw materials:

(1R)-3c-methyl-6t-isopropyl-cyclohexane-carbanilide-(1r)

(1R,2S,5R)-2-isopropyl-5-methylcyclohexane-1-carbonyl chloride

menthyl vinyl ketone

(1S,2S,5R)-2-isopropyl-5-methylcyclohexane-1-carboxylic acid

Refernces

• 1、 Mechoulam,Gaoni. "The absolute configuration of delta-1-tetrahydrocannabinol, the major active constituent of hashish.". . p. 1109 - 1111. Retrieved 1967.
• 2、 -. "Ester ammonolysis reaction catalyst composition and preparation method of L-menthane carboxamide". Paragraph 0007; 0048-0051. . Retrieved 2020/07/21.
• 3、 Koller, Sebastian,Gatzka, Julia,Wong, Kit Ming,Altmann, Philipp J.,P?thig, Alexander,Hintermann, Lukas. "Stereochemistry of the Menthyl Grignard Reagent: Generation, Composition, Dynamics, and Reactions with Electrophiles". . p. 15009 - 15028. Retrieved 2019/01/03.