(-)-menthyl bicyclo[2.2.1]hept-2-ene-5-carboxylate

Base Information

• Chemical Name: (-)-menthyl bicyclo[2.2.1]hept-2-ene-5-carboxylate
• CAS No.: 138752-03-1
• Molecular Formula: C₁₈H₂₈O₂
• Molecular Weight: 276.419
• Mol file: 138752-03-1.mol

Synonyms:(-)-menthyl bicyclo[2.2.1]hept-2-ene-5-carboxylate

Chemical Property of (-)-menthyl bicyclo[2.2.1]hept-2-ene-5-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-menthyl bicyclo[2.2.1]hept-2-ene-5-carboxylate

There total 7 articles about (-)-menthyl bicyclo[2.2.1]hept-2-ene-5-carboxylate 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: 84.0%

(1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (120-74-1,934-30-5,1195-12-6,20507-53-3,58001-99-3,67999-50-2,67999-53-5,74645-32-2,108266-75-7) + (-)-menthol (2216-51-5) → (-)-menthyl bicyclo[2.2.1]hept-2-ene-5-carboxylate (138752-03-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; for 3.08333h;

DOI:10.1021/jacs.7b01747

Reference yield: 60.0%

(-)-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)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1023/A:1012374828303

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

upstream raw materials:

(-)-menthyl acrylate

cyclopenta-1,3-diene

(1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

(-)-menthol

Downstream raw materials:

(1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

(-)-(1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl methanol

Refernces

• 1、 Hondrogiannis,Pagni,Kabalka,Kurt,Cox. "The reaction of optically active menthyl acrylate with cyclopentadiene on γ-alumina". . p. 2303 - 2306. Retrieved 1991.
• 2、 Cativiela, Carlos,Fraile, Jose M.,Garcia, Jose I.,Mayoral, Jose A.,Pires, Elisabeth,Figueras, Francois,De Menorval, Louis C.. "Effect of clay calcination on clay-catalysed Diels-Alder reactions of cyclopentadiene with methyl and (-)-menthyl acrylates". . p. 6467 - 6476. Retrieved 1992.
• 3、 Mamedov. "Asymmetrical [4+2]-cycloaddition of (-)-menthyl acrylate and (-)-menthyl methacrylate to cyclopentadiene in the presence of BBr3". . p. 217 - 222. Retrieved 2007/10/03.