(1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Base Information

• Chemical Name: (1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester
• CAS No.: 84235-36-9
• Molecular Formula: C₁₈H₂₈O₂
• Molecular Weight: 276.419
• Mol file: 84235-36-9.mol

Synonyms:(1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Chemical Property of (1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

There total 5 articles about (1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 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: 85.0%

(-)-menthyl acrylate (4835-96-5) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (84235-36-9) + (1R,2S,4R)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (84235-35-8)

Guidance literature:

(R,R)-7; at -78 ℃; for 24h; Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/ja00196a081

Reference yield:

(-)-menthyl acrylate (4835-96-5) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (-)-menthyl bicyclo[2.2.1]hept-2-ene-5-carboxylate (138752-03-1) + (1S,2R,4S)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (138752-04-2) + (1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (84235-36-9) + (1R,2S,4R)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (84235-35-8)

Guidance literature:

With diethylaluminium chloride; In toluene; at 20 ℃; for 2.5h; Product distribution; other chiral acrylates; other silica and alumina modified by Lewis acids; var. reaction times and temperatures;

DOI:10.1016/S0957-4166(00)80163-9

Reference yield:

(-)-menthyl acrylate (4835-96-5) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (-)-menthyl bicyclo[2.2.1]hept-2-ene-5-carboxylate (138752-03-1) + (1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (84235-36-9) + Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Guidance literature:

With titanium tetrachloride; In dichloromethane; at -20 ℃; for 3.5h; Product distribution; variation of Lewis acid, solvent, temperature, reaction time;

DOI:10.1016/S0040-4039(01)90516-7

upstream raw materials:

(-)-menthyl acrylate

cyclopenta-1,3-diene