4-Benzenesulfonyl-2,2-dimethyl-5-methylene-hexahydro-pentalen-1-one

Base Information

• Chemical Name: 4-Benzenesulfonyl-2,2-dimethyl-5-methylene-hexahydro-pentalen-1-one
• CAS No.: 116831-00-6
• Molecular Formula: C₁₇H₂₀O₃S
• Molecular Weight: 304.41
• Mol file: 116831-00-6.mol

Synonyms:4-Benzenesulfonyl-2,2-dimethyl-5-methylene-hexahydro-pentalen-1-one

Chemical Property of 4-Benzenesulfonyl-2,2-dimethyl-5-methylene-hexahydro-pentalen-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Benzenesulfonyl-2,2-dimethyl-5-methylene-hexahydro-pentalen-1-one

There total 7 articles about 4-Benzenesulfonyl-2,2-dimethyl-5-methylene-hexahydro-pentalen-1-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: 39.0%

5,5-dimethylcyclopent-2-enone (17197-84-1) + 2-(chloromethyl)-3-(phenylsulfonyl)-1-propene (116830-92-3) → 4-Benzenesulfonyl-2,2-dimethyl-5-methylene-hexahydro-pentalen-1-one (116831-00-6)

Guidance literature:

With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; 1,2-bis-(diphenylphosphino)ethane; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In dichloromethane; water; for 48h; Ambient temperature;

DOI:10.1016/S0040-4039(00)80053-2

Reference yield: 29.0%

5,5-dimethylcyclopent-2-enone (17197-84-1) + ethyl 2-(benzenesulfonylmethyl)-2-propenyl carbonate (117036-93-8) → (3aR,4R,6aR)-4-Benzenesulfonyl-2,2-dimethyl-5-methylene-hexahydro-pentalen-1-one (116831-00-6)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran;

Reference yield:

1-(phenylsulfonyl)-2-methyl-2-propene (49639-05-6) → (3aR,4R,6aR)-4-Benzenesulfonyl-2,2-dimethyl-5-methylene-hexahydro-pentalen-1-one (116831-00-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 58 percent / sulfuryl cloride / CH₂Cl₂ / Heating; 1.) 15 min; 2.) reflux 30 min

2: 100 percent / formic acid / 48 h / Heating

3: 63 percent / 1N HCl / methanol / Ambient temperature

4: 87 percent / pyridine / diethyl ether / 24 h / 0 - 10 °C

5: 29 percent / Pd₂(DBA)3 (CHCl₃) / tetrahydrofuran

With pyridine; hydrogenchloride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; formic acid; sulfuryl dichloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

upstream raw materials:

5,5-dimethylcyclopent-2-enone

2-(chloromethyl)-3-(phenylsulfonyl)-1-propene

ethyl 2-(benzenesulfonylmethyl)-2-propenyl carbonate

1-(phenylsulfonyl)-2-methyl-2-propene

Downstream raw materials:

4-((1R,3aR,6aR)-1-Benzenesulfonyl-5,5-dimethyl-2,4-dioxo-octahydro-pentalen-1-yl)-butyric acid ethyl ester

(3aR,4R,6aR)-4-Benzenesulfonyl-2,2-dimethyl-hexahydro-pentalene-1,5-dione