[1S-(1alpha,2beta,5alpha)]-2-(isopropyl)-5-methylcyclohexyl benzoate

Base Information

• Chemical Name: [1S-(1alpha,2beta,5alpha)]-2-(isopropyl)-5-methylcyclohexyl benzoate
• CAS No.: 58641-29-5
• Molecular Formula: C17H24 O2
• Molecular Weight: 260.376
• European Community (EC) Number: 261-374-0
• DSSTox Substance ID: DTXSID101163909
• Nikkaji Number: J296.993I
• Mol file: 58641-29-5.mol

Synonyms:58641-29-5;[1S-(1alpha,2beta,5alpha)]-2-(isopropyl)-5-methylcyclohexyl benzoate;d-menthyl benzoate;(1S-(1alpha,2beta,5alpha))-2-(Isopropyl)-5-methylcyclohexyl benzoate;SCHEMBL15498193;DTXSID101163909;Cyclohexanol, 5-methyl-2-(1-methylethyl)-, 1-benzoate, (1S,2R,5S)-

Chemical Property of [1S-(1alpha,2beta,5alpha)]-2-(isopropyl)-5-methylcyclohexyl benzoate

Chemical Property:

• PSA: 26.30000
• LogP: 4.30420
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 260.177630004
• Heavy Atom Count: 19
• Complexity: 292

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(C(C1)OC(=O)C2=CC=CC=C2)C(C)C
• Isomeric SMILES: C[C@H]1CC[C@@H]([C@H](C1)OC(=O)C2=CC=CC=C2)C(C)C

Technology Process of [1S-(1alpha,2beta,5alpha)]-2-(isopropyl)-5-methylcyclohexyl benzoate

There total 55 articles about [1S-(1alpha,2beta,5alpha)]-2-(isopropyl)-5-methylcyclohexyl benzoate 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: 100.0%

(-)-menthol (2216-51-5) + benzoic acid anhydride (93-97-0) → L-menthyl benzoate (612-33-9,31481-49-9,38649-18-2,50465-37-7,58641-29-5,71617-14-6,87038-98-0,88764-74-3,88764-75-4,91840-42-5,6284-35-1)

Guidance literature:

With 1-[bis(trifluoromethanesulfonyl)methyl]-2,3,4,5,6-pentafluorobenzene;

DOI:10.1002/1521-3773(20011105)40:21<4077::AID-ANIE4077>3.0.CO;2-1

Reference yield: 97.0%

(-)-menthol (2216-51-5) + N-methyl-N-phenyl-benzamide (1934-92-5) → L-menthyl benzoate (612-33-9,31481-49-9,38649-18-2,50465-37-7,58641-29-5,71617-14-6,87038-98-0,88764-74-3,88764-75-4,91840-42-5,6284-35-1)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; 1,3-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene; In toluene; at 80 ℃; for 12h; Inert atmosphere;

DOI:10.1021/acs.orglett.6b01758

Reference yield: 95.0%

(-)-menthol (2216-51-5) + benzoyl chloride (98-88-4) → L-menthyl benzoate (612-33-9,31481-49-9,38649-18-2,50465-37-7,58641-29-5,71617-14-6,87038-98-0,88764-74-3,88764-75-4,91840-42-5,6284-35-1)

Guidance literature:

(-)-menthol; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 25 ℃;

benzoyl chloride; In tetrahydrofuran; hexane; dichloromethane; for 2h;

DOI:10.1080/00397919708005004

upstream raw materials:

(1S,2R,5S)-(+)-menthol

benzoyl chloride

Potassium benzoate

benzoic acid anhydride

Downstream raw materials:

benzoic acid methyl ester

(1S,2R,5S)-(+)-menthol

(S)-2-p-tolylsulfinylmethylphenyl ketone

(R)-p-tolylsulfinylacetophenone

Refernces

• 1、 Huang, Changyu,Li, Jinpeng,Wang, Jiaquan,Zheng, Qingshu,Li, Zhenhua,Tu, Tao. "Hydrogen-bond-assisted transition-metal-free catalytic transformation of amides to esters". . p. 66 - 71. Retrieved 2020/11/18.
• 2、 Nikitas, Nikolaos F.,Apostolopoulou, Mary K.,Skolia, Elpida,Tsoukaki, Anna,Kokotos, Christoforos G.. "Photochemical Activation of Aromatic Aldehydes: Synthesis of Amides, Hydroxamic Acids and Esters". . p. 7915 - 7922. Retrieved 2021/05/03.