((4aR,9aR)-1,2,3,4,4a,9a-hexahydro-9H-carbazol-9-yl)(phenyl)methanone

Base Information

• Chemical Name: ((4aR,9aR)-1,2,3,4,4a,9a-hexahydro-9H-carbazol-9-yl)(phenyl)methanone
• CAS No.: 35682-32-7
• Molecular Formula: C₁₉H₁₉NO
• Molecular Weight: 277.366
• Mol file: 35682-32-7.mol

Synonyms:

Chemical Property of ((4aR,9aR)-1,2,3,4,4a,9a-hexahydro-9H-carbazol-9-yl)(phenyl)methanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((4aR,9aR)-1,2,3,4,4a,9a-hexahydro-9H-carbazol-9-yl)(phenyl)methanone

There total 4 articles about ((4aR,9aR)-1,2,3,4,4a,9a-hexahydro-9H-carbazol-9-yl)(phenyl)methanone 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%

N-[(1R,2R)-2-(2-bromophenyl)cyclohexyl]benzamide → ((4aR,9aR)-1,2,3,4,4a,9a-hexahydro-9H-carbazol-9-yl)(phenyl)methanone (35682-32-7,35682-33-8,101889-84-3)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane; caesium carbonate; In toluene; at 105 ℃; for 20h; Inert atmosphere;

DOI:10.1002/adsc.201601135

Reference yield:

2-(2-bromophenyl)-cyclohexanone (31908-20-0) → ((4aR,9aR)-1,2,3,4,4a,9a-hexahydro-9H-carbazol-9-yl)(phenyl)methanone (35682-32-7,35682-33-8,101889-84-3)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene-4-sulfonic acid / toluene / Reflux; Dean-Stark

2: bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen; (S)-binapine / dichloromethane / 20 h / 20 °C / 30402 Torr / Glovebox; Inert atmosphere; Autoclave; Green chemistry

3: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane; caesium carbonate / toluene / 20 h / 105 °C / Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; trifuran-2-yl-phosphane; (S)-binapine; hydrogen; caesium carbonate; toluene-4-sulfonic acid; In dichloromethane; toluene; 3: |Buchwald-Hartwig Coupling;

DOI:10.1002/adsc.201601135

Reference yield:

N-(2'-bromo-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)benzamide → ((4aR,9aR)-1,2,3,4,4a,9a-hexahydro-9H-carbazol-9-yl)(phenyl)methanone (35682-32-7,35682-33-8,101889-84-3)

Guidance literature:

Multi-step reaction with 2 steps

1: bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen; (S)-binapine / dichloromethane / 20 h / 20 °C / 30402 Torr / Glovebox; Inert atmosphere; Autoclave; Green chemistry

2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane; caesium carbonate / toluene / 20 h / 105 °C / Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; trifuran-2-yl-phosphane; (S)-binapine; hydrogen; caesium carbonate; In dichloromethane; toluene; 2: |Buchwald-Hartwig Coupling;

DOI:10.1002/adsc.201601135

upstream raw materials:

benzoyl chloride

cis-2,3,4,4a,9,9a-hexahydro-1H-carbazole

2-(2-bromophenyl)-cyclohexanone