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

Base Information

• Chemical Name: bis(2,2,2-trifluoroethyl) (5S,6R,9S)-6-(3-methoxyphenyl)-4-oxo-2-phenyl-9-vinyl-3-oxa-1-azaspiro[4.4]non-1-ene-7,7-dicarboxylate
• CAS No.: 1314387-64-8
• Molecular Formula: C₂₈H₂₃F₆NO₇
• Molecular Weight: 599.484
• Mol file: 1314387-64-8.mol

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

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

There total 4 articles about bis(2,2,2-trifluoroethyl) (5S,6R,9S)-6-(3-methoxyphenyl)-4-oxo-2-phenyl-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: 84.0%

(4Z)-4-(3-methoxybenzylidene)-2-phenyloxazol-5(4H)-one (82301-50-6,82301-53-9,113697-03-3) + malonic acid di(2,2,2-trifluoroethyl ester) (104883-33-2) → bis(2,2,2-trifluoroethyl) (5S,6R,9S)-6-(3-methoxyphenyl)-4-oxo-2-phenyl-9-vinyl-3-oxa-1-azaspiro[4.4]non-1-ene-7,7-dicarboxylate (1314387-64-8)

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; Inert atmosphere;

DOI:10.1021/ja309003x DOI:10.1021/ja309003x

Reference yield: 84.0%

bis(2,2,2-trifluoroethyl) 2-vinylcyclopropane-1,1-dicarboxylate (1314387-45-5) + (4Z)-4-(3-methoxybenzylidene)-2-phenyloxazol-5(4H)-one (82301-50-6,82301-53-9,113697-03-3) → bis(2,2,2-trifluoroethyl) (5S,6R,9S)-6-(3-methoxyphenyl)-4-oxo-2-phenyl-9-vinyl-3-oxa-1-azaspiro[4.4]non-1-ene-7,7-dicarboxylate (1314387-64-8)

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 16h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1002/anie.201101684

Reference yield:

Hippuric Acid (495-69-2,140480-84-8,21251-67-2,91787-63-2,66407-11-2) + 3-methoxy-benzaldehyde (591-31-1) → bis(2,2,2-trifluoroethyl) (5S,6R,9S)-6-(3-methoxyphenyl)-4-oxo-2-phenyl-9-vinyl-3-oxa-1-azaspiro[4.4]non-1-ene-7,7-dicarboxylate (1314387-64-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium acetate; acetic anhydride / tetrahydrofuran / 3 h / 60 °C / Inert atmosphere

2: trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl); tris(dibenzylideneacetone)dipalladium(0) chloroform complex / toluene / 16 h / 20 °C / Inert atmosphere

With trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl); tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium acetate; acetic anhydride; In tetrahydrofuran; toluene;

DOI:10.1002/anie.201101684

upstream raw materials:

Hippuric Acid

3-methoxy-benzaldehyde

bis(2,2,2-trifluoroethyl) 2-vinylcyclopropane-1,1-dicarboxylate

(4Z)-4-(3-methoxybenzylidene)-2-phenyloxazol-5(4H)-one