endo-2-hydroxy-exo-3-(phenylsulfenyl)-5-cyano-6,6-diphenylbicyclo<3.1.0>hexane

Base Information

• Chemical Name: endo-2-hydroxy-exo-3-(phenylsulfenyl)-5-cyano-6,6-diphenylbicyclo<3.1.0>hexane
• CAS No.: 75011-44-8
• Molecular Formula: C₂₅H₂₁NOS
• Molecular Weight: 383.514
• Mol file: 75011-44-8.mol

Synonyms:endo-2-hydroxy-exo-3-(phenylsulfenyl)-5-cyano-6,6-diphenylbicyclo<3.1.0>hexane

Chemical Property of endo-2-hydroxy-exo-3-(phenylsulfenyl)-5-cyano-6,6-diphenylbicyclo<3.1.0>hexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of endo-2-hydroxy-exo-3-(phenylsulfenyl)-5-cyano-6,6-diphenylbicyclo<3.1.0>hexane

There total 4 articles about endo-2-hydroxy-exo-3-(phenylsulfenyl)-5-cyano-6,6-diphenylbicyclo<3.1.0>hexane 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: 83.0%

exo-3-(phenylsulfenyl)-5-cyano-6,6-diphenylbicyclo<3.1.0>hexan-2-one (75045-13-5) → endo-2-hydroxy-exo-3-(phenylsulfenyl)-5-cyano-6,6-diphenylbicyclo<3.1.0>hexane (75011-44-8)

Guidance literature:

With sodium tetrahydroborate; In methanol; for 2h; Ambient temperature;

DOI:10.1021/jo01312a013

Reference yield:

3-oxocyclopent-1-ene-1-carbonitrile (34250-16-3) → endo-2-hydroxy-exo-3-(phenylsulfenyl)-5-cyano-6,6-diphenylbicyclo<3.1.0>hexane (75011-44-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / diethyl ether / 1080 h / Ambient temperature

2: 1) LDA, 2) HMPA / 1) -78 deg C, 30 min, THF, hexane, 2) room temperature, 1 h

3: 83 percent / NaBH₄ / methanol / 2 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; lithium diisopropyl amide; In methanol; diethyl ether;

DOI:10.1021/jo01312a013

Reference yield:

5-cyano-6,6-diphenylbicyclo<3.1.0>hexan-2-one (75011-39-1) → endo-2-hydroxy-exo-3-(phenylsulfenyl)-5-cyano-6,6-diphenylbicyclo<3.1.0>hexane (75011-44-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) LDA, 2) HMPA / 1) -78 deg C, 30 min, THF, hexane, 2) room temperature, 1 h

2: 83 percent / NaBH₄ / methanol / 2 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; lithium diisopropyl amide; In methanol;

DOI:10.1021/jo01312a013

upstream raw materials:

exo-3-(phenylsulfenyl)-5-cyano-6,6-diphenylbicyclo<3.1.0>hexan-2-one

3-oxocyclopent-1-ene-1-carbonitrile

5-cyano-6,6-diphenylbicyclo<3.1.0>hexan-2-one

diazodiphenylmethane

Downstream raw materials:

exo-2-chloro-exo-3-(phenylsulfenyl)-5-cyano-6,6-diphenylbicyclo<3.1.0>hexane

endo-2-hydroxy-exo-3-(phenylsulfenyl)-5-cyano-6,6-diphenylbicyclo<3.1.0>hexyl methanesulfonate