(1S,2R,5R,2'S)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl endo-2-bicyclo<2.2.1>heptanecarboxylate

Base Information

• Chemical Name: (1S,2R,5R,2'S)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl endo-2-bicyclo<2.2.1>heptanecarboxylate
• CAS No.: 100101-46-0
• Molecular Formula: C₂₄H₃₂O₂
• Molecular Weight: 352.517
• Mol file: 100101-46-0.mol

Synonyms:

Chemical Property of (1S,2R,5R,2'S)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl endo-2-bicyclo<2.2.1>heptanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,5R,2'S)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl endo-2-bicyclo<2.2.1>heptanecarboxylate

There total 7 articles about (1S,2R,5R,2'S)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl endo-2-bicyclo<2.2.1>heptanecarboxylate 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%

(-)-8-phenylmenthyl acrylate (72526-00-2) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → 5-methyl-2-(1-methyl-1-phenylethyl)cyclohexylbicyclo[2.2.1]hept-5-ene-2-carboxylate (80868-49-1,100101-46-0)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 4h;

DOI:10.1021/jo9721103

Reference yield:

(-)-8-phenylmenthol (65253-04-5) → 5-methyl-2-(1-methyl-1-phenylethyl)cyclohexylbicyclo[2.2.1]hept-5-ene-2-carboxylate (80868-49-1,100101-46-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / Et₃N / CH₂Cl₂ / -10 - 25 °C

2: 97 percent / BF₃*Et₂O / CH₂Cl₂ / 4 h / 0 °C

With boron trifluoride diethyl etherate; triethylamine; In dichloromethane; 1: Esterification / 2: Cyclization;

DOI:10.1021/jo9721103

Reference yield:

(1S,2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanol (100101-42-6) → (1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1S,2R,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (80868-49-1,100101-46-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / 4-(dimethylamino)pyridine, triethylamine / CH₂Cl₂ / 1.5 h / 0 °C

2: 1.) titanium tetrachloride / 1.) dichloromethane, 0 deg C, 45 min, 2.) 4 h

With dmap; titanium tetrachloride; triethylamine; In dichloromethane;

DOI:10.1021/jo00354a032

upstream raw materials:

(-)-8-phenylmenthyl acrylate

cyclopenta-1,3-diene

(-)-8-phenylmenthol

(1S,2R,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl acrylate

Refernces

• 1、 Whitesell, James K.,Liu, Chi-Ling,Buchanan, Charles M.,Chen, Hwang-Hsing,Minton, Mark A.. "Preparation of 8-Phenylmenthol and Its Diastereomer, 2-epi,ent-8-Phenylmenthol. A Caveat". . p. 551 - 553. Retrieved 2007/10/02.