(5S,6R,9S)-bis(2,2,2-trifluoroethyl) 6-cyclohexyl-2-(3,4-dichlorophenyl)-4-oxo-9-vinyl-3-oxa-1-azaspiro[4.4]non-1-ene-7,7-dicarboxylate

Base Information

• Chemical Name: (5S,6R,9S)-bis(2,2,2-trifluoroethyl) 6-cyclohexyl-2-(3,4-dichlorophenyl)-4-oxo-9-vinyl-3-oxa-1-azaspiro[4.4]non-1-ene-7,7-dicarboxylate
• CAS No.: 1402852-72-5
• Molecular Formula: C₂₇H₂₅Cl₂F₆NO₆
• Molecular Weight: 644.395
• Mol file: 1402852-72-5.mol

Synonyms:(5S,6R,9S)-bis(2,2,2-trifluoroethyl) 6-cyclohexyl-2-(3,4-dichlorophenyl)-4-oxo-9-vinyl-3-oxa-1-azaspiro[4.4]non-1-ene-7,7-dicarboxylate

Chemical Property of (5S,6R,9S)-bis(2,2,2-trifluoroethyl) 6-cyclohexyl-2-(3,4-dichlorophenyl)-4-oxo-9-vinyl-3-oxa-1-azaspiro[4.4]non-1-ene-7,7-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6R,9S)-bis(2,2,2-trifluoroethyl) 6-cyclohexyl-2-(3,4-dichlorophenyl)-4-oxo-9-vinyl-3-oxa-1-azaspiro[4.4]non-1-ene-7,7-dicarboxylate

There total 3 articles about (5S,6R,9S)-bis(2,2,2-trifluoroethyl) 6-cyclohexyl-2-(3,4-dichlorophenyl)-4-oxo-9-vinyl-3-oxa-1-azaspiro[4.4]non-1-ene-7,7-dicarboxylate 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: 81.0%

(Z)-4-(cyclohexylmethylene)-2-(3,4-dichlorophenyl)oxazol-5(4H)-one (1402852-66-7) + malonic acid di(2,2,2-trifluoroethyl ester) (104883-33-2) → (5S,6R,9S)-bis(2,2,2-trifluoroethyl) 6-cyclohexyl-2-(3,4-dichlorophenyl)-4-oxo-9-vinyl-3-oxa-1-azaspiro[4.4]non-1-ene-7,7-dicarboxylate (1402852-72-5)

Guidance literature:

With trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl); tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In toluene; at 20 ℃; for 16.8333h; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ja309003x DOI:10.1021/ja309003x

Reference yield:

2-(3,4-dichlorobenzamido)acetic acid (17321-80-1) → (5S,6R,9S)-bis(2,2,2-trifluoroethyl) 6-cyclohexyl-2-(3,4-dichlorophenyl)-4-oxo-9-vinyl-3-oxa-1-azaspiro[4.4]non-1-ene-7,7-dicarboxylate (1402852-72-5)

Guidance literature:

Multi-step reaction with 3 steps

1: N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / dichloromethane / 1 h / Inert atmosphere

2: aluminum oxide / dichloromethane / 2 h / Inert atmosphere

3: trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl); tris(dibenzylideneacetone)dipalladium(0) chloroform complex / toluene / 16.83 h / 20 °C / Inert atmosphere

With trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl); aluminum oxide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; toluene;

DOI:10.1021/ja309003x DOI:10.1021/ja309003x

Reference yield:

2-(3,4-dichlorophenyl)oxazol-5(4H)-one (1402852-67-8) → (5S,6R,9S)-bis(2,2,2-trifluoroethyl) 6-cyclohexyl-2-(3,4-dichlorophenyl)-4-oxo-9-vinyl-3-oxa-1-azaspiro[4.4]non-1-ene-7,7-dicarboxylate (1402852-72-5)

Guidance literature:

Multi-step reaction with 2 steps

1: aluminum oxide / dichloromethane / 2 h / Inert atmosphere

2: trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl); tris(dibenzylideneacetone)dipalladium(0) chloroform complex / toluene / 16.83 h / 20 °C / Inert atmosphere

With trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl); aluminum oxide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In dichloromethane; toluene;

DOI:10.1021/ja309003x DOI:10.1021/ja309003x

upstream raw materials:

2-(3,4-dichlorobenzamido)acetic acid

2-(3,4-dichlorophenyl)oxazol-5(4H)-one

(Z)-4-(cyclohexylmethylene)-2-(3,4-dichlorophenyl)oxazol-5(4H)-one

malonic acid di(2,2,2-trifluoroethyl ester)