Bicyclo[3.1.1]heptan-2-one, 6,6-dimethyl-3-(phenylmethylene)-, (1R,3E,5R)-

Base Information

• Chemical Name: Bicyclo[3.1.1]heptan-2-one, 6,6-dimethyl-3-(phenylmethylene)-, (1R,3E,5R)-
• CAS No.: 118712-10-0
• Molecular Formula: C16H18O
• Molecular Weight: 226.318
• Mol file: 118712-10-0.mol

Synonyms:

Chemical Property of Bicyclo[3.1.1]heptan-2-one, 6,6-dimethyl-3-(phenylmethylene)-, (1R,3E,5R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Bicyclo[3.1.1]heptan-2-one, 6,6-dimethyl-3-(phenylmethylene)-, (1R,3E,5R)-

There total 3 articles about Bicyclo[3.1.1]heptan-2-one, 6,6-dimethyl-3-(phenylmethylene)-, (1R,3E,5R)- 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%

(1R,5S)-(+)-nopinone (38651-65-9) + benzaldehyde (100-52-7) → (1R,3E,5R)-(-)-3-benzylidene nopinone (118712-10-0)

Guidance literature:

With sodium hydroxide; In water; for 8h; Inert atmosphere; Reflux;

DOI:10.2174/15701808113106660095

Reference yield:

beta-pinene (18172-67-3,19902-08-0,25719-60-2) → (1R,3E,5R)-(-)-3-benzylidene nopinone (118712-10-0)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid; potassium permanganate / acetone / 15 - 20 °C / Inert atmosphere

2: sodium hydroxide / water / 8 h / Inert atmosphere; Reflux

With potassium permanganate; sulfuric acid; sodium hydroxide; In water; acetone;

DOI:10.2174/15701808113106660095

Reference yield:

beta-pinene (18172-67-3,19902-08-0,25719-60-2) → (1R,3E,5R)-(-)-3-benzylidene nopinone (118712-10-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) CH₂Cl₂, MeOH, -78 deg C to RT, 18 h

2: 10percent aq. KOH / 24 h / 100 °C

With potassium hydroxide; dimethylsulfide; ozone;

DOI:10.1016/S0957-4166(96)00523-X

upstream raw materials:

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

benzaldehyde

beta-pinene

Downstream raw materials:

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

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

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

(1R,2S,5R)-6,6-Dimethyl-3-[1-phenyl-meth-(E)-ylidene]-bicyclo[3.1.1]heptan-2-ol

Refernces

• 1、 Dumas, Francoise,Alencar, Karla,Mahuteau, Jacqueline,Barbero, Maria J. L.,Miet, Christine,Gerard, Flavien,Vasconcellos, Mario L. A. A.,Costa, Paulo R. R.. "Synthesis and structural determination of new chiral auxiliaries derived from (-)-β-pinene". . p. 579 - 583. Retrieved 2007/10/03.