(R)-methyl 3-(4-methyl-6-oxocyclohex-1-enyl)propanoate

Base Information

• Chemical Name: (R)-methyl 3-(4-methyl-6-oxocyclohex-1-enyl)propanoate
• CAS No.: 1042150-18-4
• Molecular Formula: C₁₁H₁₆O₃
• Molecular Weight: 196.246
• Mol file: 1042150-18-4.mol

Synonyms:(R)-methyl 3-(4-methyl-6-oxocyclohex-1-enyl)propanoate

Chemical Property of (R)-methyl 3-(4-methyl-6-oxocyclohex-1-enyl)propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-methyl 3-(4-methyl-6-oxocyclohex-1-enyl)propanoate

There total 2 articles about (R)-methyl 3-(4-methyl-6-oxocyclohex-1-enyl)propanoate 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: 78.0%

C14H16O2 + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → (R)-methyl 3-(4-methyl-6-oxocyclohex-1-enyl)propanoate (1042150-18-4)

Guidance literature:

C₁₄H₁₆O₂; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h; Inert atmosphere;

acrylic acid methyl ester; In N,N-dimethyl-d₆-formamide; at 0 - 40 ℃; for 16h; Inert atmosphere;

DOI:10.1021/acs.orglett.6b02322

Reference yield:

pulegone (89-82-7,90449-51-7) → (R)-methyl 3-(4-methyl-6-oxocyclohex-1-enyl)propanoate (1042150-18-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dihydrogen peroxide; lithium hydroxide

1.3: Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene

With dihydrogen peroxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium hydroxide;

DOI:10.1021/acs.orglett.6b02072

Reference yield: 99.0%

(R)-methyl 3-(4-methyl-6-oxocyclohex-1-enyl)propanoate (1042150-18-4) + allyl-trimethyl-silane (762-72-1) → methyl 3-((2R,4R)-2-allyl-4-methyl-6-oxocyclohexyl)propanoate

Guidance literature:

With indium(III) chloride; chloro-trimethyl-silane; diastereoselective reaction;

DOI:10.1021/acs.orglett.7b00492

upstream raw materials:

acrylic acid methyl ester

pulegone

Downstream raw materials:

(-)-8-deoxyserratinine

lycopodine

Refernces

• 1、 Ma, Donghui,Zhong, Zhuliang,Liu, Zaimin,Zhang, Mingjie,Xu, Shiyan,Xu, Dengyu,Song, Dengpeng,Xie, Xingang,She, Xuegong. "Protecting-Group-Free Total Synthesis of (-)-Lycopodine via Phosphoric Acid Promoted Alkyne Aza-Prins Cyclization". . p. 4328 - 4331. Retrieved 2016/11/09.