(+)-cis-3-bromonopinone

Base Information

• Chemical Name: (+)-cis-3-bromonopinone
• CAS No.: 28239-06-7
• Molecular Formula: C₉H₁₃BrO
• Molecular Weight: 217.106
• Mol file: 28239-06-7.mol

Synonyms:(+)-cis-3-bromonopinone

Chemical Property of (+)-cis-3-bromonopinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (+)-cis-3-bromonopinone

There total 2 articles about (+)-cis-3-bromonopinone 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: 55.0%

(1R,5S)-(+)-nopinone (38651-65-9) → (1R,5R)-3-bromo-6,6-dimethylbicyclo<3.1.1>-heptan-2-one (1610-50-0,28239-06-7,28239-07-8,35512-52-8,52610-68-1) + (1R,5R)-3,3-dibromo-6,6-dimethylbicyclo<3.1.1>-heptan-2-one (145104-70-7)

Guidance literature:

With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 48h; Heating;

DOI:10.1016/S0040-4020(01)85608-8

Reference yield: 37.0%

(1R,5S)-(+)-nopinone (38651-65-9) → (+)-cis-3-bromonopinone (28239-06-7)

Guidance literature:

With N-Bromosuccinimide; Perbenzoic acid; In tetrachloromethane; for 3h; Heating;

DOI:10.1021/ja00528a036

Reference yield:

(+)-cis-3-bromonopinone (28239-06-7) → (1R,5S)-(+)-nopinone (38651-65-9) + (+)-apoverbenone (35408-03-8)

Guidance literature:

With lithium carbonate; lithium bromide; In dimethyl sulfoxide; at 140 - 150 ℃; for 60h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/ja00528a036

upstream raw materials:

(1R,5S)-(+)-nopinone

Downstream raw materials:

(1R,5S)-(+)-nopinone

(+)-apoverbenone

(3R,4R)-(+)-3-methyl-4-tert-butylcyclohexanone

(3R,4R)-(-)-3-methyl-4-(1-methyl-1-cyclopropyl)cyclohexanone

Refernces

• 1、 Konopelski, Joseph P.,Sundararaman, P.,Barth, Guenter,Djerassi, Carl. "Optical Rotatory Dispersion Studies. 128. Octant Contributions of Methyl Groups in 4-tert-Butylcyclohexanones". . p. 2737 - 2745. Retrieved 2007/10/02.