(2S,3S)-2-(diphenylphosphoryl)-3-isopropylcyclopentanone

Base Information

• Chemical Name: (2S,3S)-2-(diphenylphosphoryl)-3-isopropylcyclopentanone
• CAS No.: 1422017-56-8
• Molecular Formula: C₂₀H₂₃O₂P
• Molecular Weight: 326.375
• Mol file: 1422017-56-8.mol

Synonyms:(2S,3S)-2-(diphenylphosphoryl)-3-isopropylcyclopentanone

Chemical Property of (2S,3S)-2-(diphenylphosphoryl)-3-isopropylcyclopentanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-(diphenylphosphoryl)-3-isopropylcyclopentanone

There total 4 articles about (2S,3S)-2-(diphenylphosphoryl)-3-isopropylcyclopentanone 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: 71.0%

(1R, 5S)-1-(diphenylphosphoryl)-6,6-dimethylbicyclo[3.1.0]hexan-2-one (1422017-55-7) → (2S,3S)-2-(diphenylphosphoryl)-3-isopropylcyclopentanone (1422017-56-8)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 1h; Inert atmosphere; Reflux;

DOI:10.1021/ol500437m

Reference yield:

1-(diphenylphosphoryl)-6-methylhept-5-en-2-one (1422017-53-5) → (2S,3S)-2-(diphenylphosphoryl)-3-isopropylcyclopentanone (1422017-56-8)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine; 4-toluenesulfonyl azide / acetonitrile / 3 h / 20 °C

2: tetrakis(acetonitrile)copper(I) tetrafluoroborate; (4S)-2,2'-(1-phenylmethyl-2-phenylethylidene)bis[4-(1-methylethyl)-4,5-dihydrooxazole] / toluene / 12 h / 70 °C / Inert atmosphere

3: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 1 h / Reflux

With (4S)-2,2'-(1-phenylmethyl-2-phenylethylidene)bis[4-(1-methylethyl)-4,5-dihydrooxazole]; 4-toluenesulfonyl azide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; tetrakis(acetonitrile)copper(I) tetrafluoroborate; triethylamine; In toluene; acetonitrile;

DOI:10.1021/ol303459x

Reference yield:

1-diazo-1-(diphenylphosphoryl)-6-methylhept-5-en-2-one (1422017-54-6) → (2S,3S)-2-(diphenylphosphoryl)-3-isopropylcyclopentanone (1422017-56-8)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrakis(acetonitrile)copper(I) tetrafluoroborate; (4S)-2,2'-(1-phenylmethyl-2-phenylethylidene)bis[4-(1-methylethyl)-4,5-dihydrooxazole] / toluene / 12 h / 70 °C / Inert atmosphere

2: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 1 h / Reflux

With (4S)-2,2'-(1-phenylmethyl-2-phenylethylidene)bis[4-(1-methylethyl)-4,5-dihydrooxazole]; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; tetrakis(acetonitrile)copper(I) tetrafluoroborate; In toluene;

DOI:10.1021/ol303459x

upstream raw materials:

diphenyl(methyl)phosphine oxide

1-(diphenylphosphoryl)-6-methylhept-5-en-2-one

1-diazo-1-(diphenylphosphoryl)-6-methylhept-5-en-2-one

(1R, 5S)-1-(diphenylphosphoryl)-6,6-dimethylbicyclo[3.1.0]hexan-2-one