cis-3-(Methoxycarbonyl)cyclobutanecarboxylic acid

Base Information

• Chemical Name: cis-3-(Methoxycarbonyl)cyclobutanecarboxylic acid
• CAS No.: 142733-61-7
• Molecular Formula: C₇H₁₀O₄
• Molecular Weight: 158.154
• Mol file: 142733-61-7.mol

Synonyms:cis-3-(Methoxycarbonyl)cyclobutanecarboxylic acid

Chemical Property of cis-3-(Methoxycarbonyl)cyclobutanecarboxylic acid

Chemical Property:

• PSA: 63.60000
• LogP: 0.27020

Purity/Quality:

98%,99%, ^*data from raw suppliers

cis-Cyclobutane-1,3-dicarboxylicacidmono-methylester 96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of cis-3-(Methoxycarbonyl)cyclobutanecarboxylic acid

There total 9 articles about cis-3-(Methoxycarbonyl)cyclobutanecarboxylic acid 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: 100.0%

methyl 3-oxo-2-oxabicyclo<2.2.0>hept-5-ene-6-carboxylate (61752-11-2) → cis-1,3-cyclobutanedicarboxylic acid monomethyl ester (142733-61-7,116569-00-7,1401103-71-6)

Guidance literature:

With platinum on carbon; hydrogen; In tetrahydrofuran; at 20 ℃; for 16h; under 760.051 Torr;

DOI:10.1016/j.tet.2018.12.037

Reference yield: 91.0%

methanol (67-56-1) + cis-cyclobutane-1,3-dicarboxylic acid anhydride (4462-97-9) → cis-1,3-cyclobutanedicarboxylic acid monomethyl ester (142733-61-7,116569-00-7,1401103-71-6)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 10h; Ambient temperature;

Reference yield:

methyl coumalate (6018-41-3) → cis-1,3-cyclobutanedicarboxylic acid monomethyl ester (142733-61-7,116569-00-7,1401103-71-6)

Guidance literature:

Multi-step reaction with 2 steps

1: dichloromethane / 96 h / 15 °C / Photolysis; Inert atmosphere

2: 10 % platinum on carbon; hydrogen / dichloromethane

With 10 % platinum on carbon; hydrogen; In dichloromethane;

DOI:10.1021/ja209205x

upstream raw materials:

methanol

cis-1,3-Cyclobutandicarbonsaeureanhydrid

cis-cyclobutane-1,3-dicarboxylic acid anhydride

7‐phenyl‐6,8‐dioxaspiro[3.5]nonane‐2,2‐dicarboxylic acid

Downstream raw materials:

C₂₃H₂₆O₉

C₃₃H₃₆N₂O₉

C₁₄H₁₇NO₃S

cis-methyl 3-<(t-butoxycarbonyl)amino>cyclobutanecarboxylate

Refernces

• 1、 Frebault, Frederic,Maulide, Nuno. "Total synthesis and structural revision of the piperarborenines: When photochemistry meets C-H activation". . p. 2815 - 2817. Retrieved 2012/05/05.
• 2、 Pecquet, Pascal,Huet, Francois,Legraverend, Michel,Bisagni, Emile. "SYNTHESIS OF NEW CARBOCYCLIC ANALOGUES OF OXETANOCIN A AND OXETANOCIN G". . p. 739 - 745. Retrieved 2007/10/02.