(E)-3-(4-chlorophenyl)-1-((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)prop-2-en-1-one

Base Information

• Chemical Name: (E)-3-(4-chlorophenyl)-1-((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)prop-2-en-1-one
• CAS No.: 1092682-58-0
• Molecular Formula: C₁₉H₂₂ClNO₃S
• Molecular Weight: 379.908
• Mol file: 1092682-58-0.mol

Synonyms:(E)-3-(4-chlorophenyl)-1-((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)prop-2-en-1-one

Chemical Property of (E)-3-(4-chlorophenyl)-1-((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)prop-2-en-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-(4-chlorophenyl)-1-((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)prop-2-en-1-one

There total 2 articles about (E)-3-(4-chlorophenyl)-1-((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)prop-2-en-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: 87.0%

cinnamoyl chloride (35086-79-4,95602-71-4) + (+)-camphorsultam (108448-77-7,124224-04-0) → (E)-3-(4-chlorophenyl)-1-((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)prop-2-en-1-one (1092682-58-0)

Guidance literature:

(+)-camphorsultam; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.5h;

cinnamoyl chloride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃;

DOI:10.1021/jm401798r

Reference yield:

3-(4-chlorophenyl)prop-2-enoic acid (1615-02-7,940-62-5) → (E)-3-(4-chlorophenyl)-1-((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)prop-2-en-1-one (1092682-58-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: thionyl chloride / 2 h / 20 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C

2.2: 0 - 20 °C

With thionyl chloride; sodium hydride; In tetrahydrofuran; mineral oil;

DOI:10.1021/jm401798r

Reference yield: 73.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (E)-3-(4-chlorophenyl)-1-((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)prop-2-en-1-one (1092682-58-0) → ((1S,2S)-2-(4-chlorophenyl)cyclopropyl)((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)methanone (1612143-64-2)

Guidance literature:

With palladium diacetate; In diethyl ether; dichloromethane; at -10 - 20 ℃; diastereoselective reaction;

DOI:10.1016/j.bmc.2016.11.018

upstream raw materials:

cinnamoyl chloride

(+)-camphorsultam

3-(4-chlorophenyl)prop-2-enoic acid

Downstream raw materials:

(+)-(1S,2S)-2-(4-chlorophenyl)cyclopropanecarboxylic acid

tert-butyl ((1S,2R)-2-(4-chlorophenyl)cyclopropyl)carbamate

(1S,2R)-2-(4-chlorophenyl)-N-propylcyclopropan-1-amine

(1S,2R)-2-(4-chlorophenyl)cyclopropan-1-amine