methyl (1R,2R,3S,4S)-3-methylbicyclo[2.2.1]hept-5-ene-2-carboxylate

Base Information

• Chemical Name: methyl (1R,2R,3S,4S)-3-methylbicyclo[2.2.1]hept-5-ene-2-carboxylate
• CAS No.: 136375-14-9
• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.22
• Mol file: 136375-14-9.mol

Synonyms:methyl (1R,2R,3S,4S)-3-methylbicyclo[2.2.1]hept-5-ene-2-carboxylate

Chemical Property of methyl (1R,2R,3S,4S)-3-methylbicyclo[2.2.1]hept-5-ene-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1R,2R,3S,4S)-3-methylbicyclo[2.2.1]hept-5-ene-2-carboxylate

There total 17 articles about methyl (1R,2R,3S,4S)-3-methylbicyclo[2.2.1]hept-5-ene-2-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: 96.0%

methanol (67-56-1) + ((1S,2S,3R,4R)-3-Methyl-bicyclo[2.2.1]hept-5-en-2-yl)-(2-thioxo-thiazolidin-3-yl)-methanone → endo-2-carbomethoxy-exo-3-methylbicyclo[2,2,1]hept-5-ene (7167-30-8,7288-31-5,16651-51-7,17660-75-2,23217-30-3,89577-04-8,136375-14-9,155325-46-5)

Guidance literature:

With dmap; In acetonitrile; at 25 ℃;

DOI:10.1039/a900577c

Reference yield:

crotonic acid methyl ester (623-43-8) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → endo-2-carbomethoxy-exo-3-methylbicyclo[2,2,1]hept-5-ene (7167-30-8,7288-31-5,16651-51-7,17660-75-2,23217-30-3,89577-04-8,136375-14-9,155325-46-5) + exo-2-carbomethoxy-endo-3-methylbicyclo[2,2,1]hept-5-ene (7167-30-8,7288-31-5,16651-51-7,17660-75-2,23217-30-3,89577-04-8,136375-14-9)

Guidance literature:

diethylaluminium chloride; In dichloromethane; at -78 - 0 ℃; for 48h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/S0040-4039(00)94204-7

Reference yield:

crotonic acid methyl ester (623-43-8) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → endo-2-carbomethoxy-exo-3-methylbicyclo[2,2,1]hept-5-ene (7167-30-8,7288-31-5,16651-51-7,17660-75-2,23217-30-3,89577-04-8,136375-14-9,155325-46-5) + exo-2-carbomethoxy-endo-3-methylbicyclo[2,2,1]hept-5-ene (7167-30-8,7288-31-5,16651-51-7,17660-75-2,23217-30-3,89577-04-8,136375-14-9)

Guidance literature:

diethylaluminium chloride; In dichloromethane; at -78 - 0 ℃; for 48h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/S0040-4039(00)94204-7

upstream raw materials:

methyl crotonate

cyclopenta-1,3-diene

crotonic acid methyl ester

methanol

Downstream raw materials:

endo-3-methylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid

(3-endo,2-exo)-3-methylbicyclo<2.2.1>hept-5-ene-2-carboxylic acid

(2R,3S)-3-Methyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid