Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-3-(phenylsulfinyl)-, (1R)-

Base Information

• Chemical Name: Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-3-(phenylsulfinyl)-, (1R)-
• CAS No.: 142095-95-2
• Molecular Formula: C16H18O2S
• Molecular Weight: 274.384
• Mol file: 142095-95-2.mol

Synonyms:

Chemical Property of Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-3-(phenylsulfinyl)-, (1R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-3-(phenylsulfinyl)-, (1R)-

There total 1 articles about Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-3-(phenylsulfinyl)-, (1R)- 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: 92.0%

(1R,5S)-4,6,6-trimethyl-3-(phenylthio)bicyclo<3.1.1>hept-3-en-2-one (128261-66-5) → (1R,5S)-4,6,6-trimethyl-3-phenylsulfoxybicyclo<3.1.1>hept-3-en-2-one (142095-95-2)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 1h;

Reference yield:

(1R,5S)-4,6,6-trimethyl-3-phenylsulfoxybicyclo<3.1.1>hept-3-en-2-one (142095-95-2) → (3R,4S)-3-acetoxymethyl-4-isopropyl-3-vinylcyclohexanone (142185-55-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 88 percent / pyridine; H₂O / 15 h / 60 °C

2: 96 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

3: 83 percent / CuBr*Me₂S / tetrahydrofuran / 0.5 h / -78 °C

4: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 10 h / Ambient temperature

5: 91 percent / Et₃N, DMAP / CH₂Cl₂ / 20 h / Ambient temperature

6: 71 percent / BF₃*OEt₂, zinc acetate / 72 h / Ambient temperature

7: 1.) K₂CO₃, 2.) pyridine / 1.) CH₃OH, 0 deg C, 1 h, 2.) 0 deg C, 1 h; room temperature, 15 h

With pyridine; 1H-imidazole; dmap; copper(I) bromide dimethylsulfide complex; boron trifluoride diethyl etherate; zinc diacetate; tetrabutyl ammonium fluoride; potassium carbonate; triethylamine; In tetrahydrofuran; pyridine; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

(1R,5S)-4,6,6-trimethyl-3-phenylsulfoxybicyclo<3.1.1>hept-3-en-2-one (142095-95-2) → (4S,5R)-1-acetoxy-5-acetoxymethyl-4-isopropenyl-5-vinylcyclohex-1-ene (142096-00-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 88 percent / pyridine; H₂O / 15 h / 60 °C

2: 96 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

3: 83 percent / CuBr*Me₂S / tetrahydrofuran / 0.5 h / -78 °C

4: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 10 h / Ambient temperature

5: 91 percent / Et₃N, DMAP / CH₂Cl₂ / 20 h / Ambient temperature

6: 71 percent / BF₃*OEt₂, zinc acetate / 72 h / Ambient temperature

With 1H-imidazole; dmap; copper(I) bromide dimethylsulfide complex; boron trifluoride diethyl etherate; zinc diacetate; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; pyridine; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

(1R,5S)-4,6,6-trimethyl-3-(phenylthio)bicyclo<3.1.1>hept-3-en-2-one

Downstream raw materials:

(3R,4S)-3-acetoxymethyl-4-isopropyl-3-vinylcyclohexanone

(4S,5R)-1-acetoxy-5-acetoxymethyl-4-isopropenyl-5-vinylcyclohex-1-ene