cis-(+/-)-2-allyl-3-hydroxy-2-methylcyclopentanone

Base Information

• Chemical Name: cis-(+/-)-2-allyl-3-hydroxy-2-methylcyclopentanone
• CAS No.: 81969-80-4
• Molecular Formula: C₉H₁₄O₂
• Molecular Weight: 154.209
• Mol file: 81969-80-4.mol

Synonyms:

Chemical Property of cis-(+/-)-2-allyl-3-hydroxy-2-methylcyclopentanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cis-(+/-)-2-allyl-3-hydroxy-2-methylcyclopentanone

There total 4 articles about cis-(+/-)-2-allyl-3-hydroxy-2-methylcyclopentanone 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:

2-allyl-2-methyl-1,3-cyclopentanedione (26828-48-8) → trans-(+/-)-2-allyl-3-hydroxy-2-methylcyclopentanone + cis-(+/-)-2-allyl-3-hydroxy-2-methylcyclopentanone (42050-72-6,72345-34-7,81969-79-1,81969-80-4,81969-81-5,109120-84-5,109120-85-6)

Guidance literature:

With sodium tetrahydroborate; In 1,2-dimethoxyethane; at -60 ℃; for 20h; Title compound not separated from byproducts.;

DOI:10.1016/j.tet.2008.01.065

Reference yield:

2-allyl-2-methyl-1,3-cyclopentanedione (26828-48-8) → (+)-(2S,3S)-3-Hydroxy-2-methyl-2-(prop-2-enyl)-cyclopentanon (72345-34-7) + (2S,3R)-2-allyl-3-hydroxy-2-methylcyclopentan-1-one (81969-80-4) + (2S,3S)-2-allyl-3-hydroxy-2-methylcyclopentan-1-one (109120-84-5) + (2R,3S)-3-hydroxy-2-methyl-2-(2-propenyl)cyclopentan-1-one (109120-85-6)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; for 3h; Yield given. Yields of byproduct given;

DOI:10.1021/jo00391a009

Reference yield:

2-allyl-2-methyl-1,3-cyclopentanedione (26828-48-8) → (+)-(2S,3S)-3-Hydroxy-2-methyl-2-(prop-2-enyl)-cyclopentanon (72345-34-7) + (2S,3R)-2-allyl-3-hydroxy-2-methylcyclopentan-1-one (81969-80-4)

Guidance literature:

With borane-THF; dihydroxy-methyl-borane; (2S,3R)-2-amino-3-(tert-butyldimethylsilyloxy)-1,1-diphenylbutan-1-ol; In tetrahydrofuran; at 20 ℃; for 19h; Title compound not separated from byproducts;

DOI:10.1016/S0957-4166(00)00378-5

upstream raw materials:

2-allyl-2-methyl-1,3-cyclopentanedione

Refernces

• 1、 Carr, Jeremy M.,Snowden, Timothy S.. "Comparative reductive desymmetrization of 2,2-disubstituted-cycloalkane-1,3-diones". . p. 2897 - 2905. Retrieved 2008/09/20.
• 2、 Brooks, Dee W.,Mazdiyasni, Hormoz,Grothaus, Paul G.. "Asymmetric Microbial Reduction of Prochiral 2,2-Disubstituted Cycloalkanediones". . p. 3223 - 3232. Retrieved 2007/10/02.