(1R,3S,5R)-6,6-dimethyl-3-(phenylselanyl)bicyclo[3.1.1]heptan-2-one

Base Information

• Chemical Name: (1R,3S,5R)-6,6-dimethyl-3-(phenylselanyl)bicyclo[3.1.1]heptan-2-one
• CAS No.: 135432-16-5
• Molecular Formula: C₁₅H₁₈OSe
• Molecular Weight: 293.267
• Mol file: 135432-16-5.mol

Synonyms:(1R,3S,5R)-6,6-dimethyl-3-(phenylselanyl)bicyclo[3.1.1]heptan-2-one

Chemical Property of (1R,3S,5R)-6,6-dimethyl-3-(phenylselanyl)bicyclo[3.1.1]heptan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3S,5R)-6,6-dimethyl-3-(phenylselanyl)bicyclo[3.1.1]heptan-2-one

There total 3 articles about (1R,3S,5R)-6,6-dimethyl-3-(phenylselanyl)bicyclo[3.1.1]heptan-2-one 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: 89.0%

(1R,5S)-(+)-nopinone (38651-65-9) + diphenyl diselenide (1666-13-3) → (1R,3S,5R)-6,6-dimethyl-3-(phenylselanyl)bicyclo[3.1.1]heptan-2-one (135432-16-5)

Guidance literature:

With selenium(IV) oxide; sulfuric acid; In methanol; at 20 ℃; for 5h; Cooling with ice;

DOI:10.1002/chem.201303538

Reference yield:

(1R,5S)-(+)-nopinone (38651-65-9) + Phenylselenyl bromide (34837-55-3) → (1R,3S,5R)-6,6-dimethyl-3-(phenylseleno)bicyclo<3.1.1>heptan-2-one (135503-45-6) + (1R,3S,5R)-6,6-dimethyl-3-(phenylselanyl)bicyclo[3.1.1]heptan-2-one (135432-16-5)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given; 1) THF, -78 deg C, 30 min, 2) THF, 5 min;

DOI:10.1021/jo00024a031

Reference yield:

beta-pinene (18172-67-3,19902-08-0,25719-60-2) → (1R,3S,5R)-6,6-dimethyl-3-(phenylselanyl)bicyclo[3.1.1]heptan-2-one (135432-16-5)

Guidance literature:

Multi-step reaction with 2 steps

1: rhodium(III) chloride hydrate; sodium periodate / tetrachloromethane; acetonitrile; water / 2 h / 20 °C

2: selenium(IV) oxide; sulfuric acid / methanol / 5 h / 20 °C / Cooling with ice

With selenium(IV) oxide; sodium periodate; rhodium(III) chloride hydrate; sulfuric acid; In methanol; tetrachloromethane; water; acetonitrile;

DOI:10.1002/chem.201303538

upstream raw materials:

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

Phenylselenyl bromide

beta-pinene

diphenyl diselenide

Downstream raw materials:

(+)-apoverbenone

1-methoxy-4-((1R,2R,5R)-5-methyl-2-(prop-1-en-2-yl)-5-vinylcyclohexyl)benzene

cyclobackuchiol B