dimethyl 3β-methylcyclopropane-1α,2α-dicarboxylate

Base Information

• Chemical Name: dimethyl 3β-methylcyclopropane-1α,2α-dicarboxylate
• CAS No.: 14661-79-1
• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.181
• Mol file: 14661-79-1.mol

Synonyms:dimethyl 3β-methylcyclopropane-1α,2α-dicarboxylate

Chemical Property of dimethyl 3β-methylcyclopropane-1α,2α-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl 3β-methylcyclopropane-1α,2α-dicarboxylate

There total 2 articles about dimethyl 3β-methylcyclopropane-1α,2α-dicarboxylate 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: 20.0%

crotonic acid methyl ester (623-43-8) + (Dimethylsulfuranyliden)essigsaeure-methylester (103548-67-0) → dimethyl 3β-methylcyclopropane-1α,2α-dicarboxylate (14661-79-1) + methyl 3-methylcyclopropane-1α,2β-dicarboxylate (28363-79-3) + dimethyl trans-1,2-cyclopropanedicarboxylate (826-35-7) + dimethylfumarate (624-49-7)

Guidance literature:

In dichloromethane; for 22h; Heating;

Reference yield:

1,1-Dibromoethane (557-91-5) + dimethyl cis-but-2-ene-1,4-dioate (624-48-6) → dimethyl 3β-methylcyclopropane-1α,2α-dicarboxylate (14661-79-1) + methyl 3-methylcyclopropane-1α,2β-dicarboxylate (28363-79-3) + dimethyl 3α-methylcyclopropane-1α,2α-dicarboxylate (87421-39-4) + Dimethyl succinate (106-65-0)

Guidance literature:

With sodium iodide; nickel dibromide; zinc; Yield given. Yields of byproduct given; 1.) acetonitrile, RT, 2.) acetonitrile, RT, 27 h;

DOI:10.1246/bcsj.56.1592

Reference yield:

dimethyl 3β-methylcyclopropane-1α,2α-dicarboxylate (14661-79-1) → (1S,2R,3R)-2-(Methoxycarbonyl)-3-methylcyclopropane-1-carboxylic acid (139156-61-9,613681-19-9) + (1R,2S,3S)-2-(Methoxycarbonyl)-3-methylcyclopropane-1-carboxylic acid (139156-61-9,613681-19-9)

Guidance literature:

With sodium hydroxide; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature; pig liver esterase, pH 7.5-8.0 (phosphate buffer);

DOI:10.1002/hlca.19910740832

upstream raw materials:

crotonic acid methyl ester

(Dimethylsulfuranyliden)essigsaeure-methylester

1,1-Dibromoethane

dimethyl cis-but-2-ene-1,4-dioate

Downstream raw materials:

(1S,2R,3R)-2-(Methoxycarbonyl)-3-methylcyclopropane-1-carboxylic acid

(1R,2S,3S)-2-(Methoxycarbonyl)-3-methylcyclopropane-1-carboxylic acid

(1S,2S)-(+)-trans-2-methylcyclopropanecarboxylic acid

Refernces

• 1、 Kanai,Nishiguchi,Matsuda. "CYCLOPROPANATION OF DIMETHYL FUMARATE AND MALEATE WITH GEM-DIHALIDES CATALYZED BY Co(0)- OR Ni(0)-COMPLEX AND ZINC.". . p. 1592 - 1597. Retrieved 2007/10/02.