ethyl 4-oxo-2,9-diphenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-6-carboxylate

Base Information

• Chemical Name: ethyl 4-oxo-2,9-diphenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-6-carboxylate
• CAS No.: 1361329-65-8
• Molecular Formula: C₂₂H₁₉NO₄
• Molecular Weight: 361.397
• Mol file: 1361329-65-8.mol

Synonyms:ethyl 4-oxo-2,9-diphenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-6-carboxylate

Chemical Property of ethyl 4-oxo-2,9-diphenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-6-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 4-oxo-2,9-diphenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-6-carboxylate

There total 3 articles about ethyl 4-oxo-2,9-diphenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-6-carboxylate 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: 77.0%

ethyl 2,3-butadienoate (14369-81-4) + 4-benzylidene-2-phenyloxazole-5(4H)-one (842-74-0,5839-91-8) → ethyl 4-oxo-2,9-diphenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-6-carboxylate (1361329-65-8)

Guidance literature:

With (11aR)-(+)-5,6,10,11,12,13-hexahydro-5-phenyl-4H-diindeno[7,1-cd:1,7-ef]phosphocin; In dichloromethane; at 20 ℃; for 8h; optical yield given as %ee; enantioselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1039/c2cc17709a

Reference yield:

ethyl 2,3-butadienoate (14369-81-4) + (4Z)-4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-one (17606-70-1,5839-91-8) → C22H19NO4 (1361559-72-9) + ethyl 4-oxo-2,9-diphenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-6-carboxylate (1361329-65-8) + (5S,9R)-ethyl 4-oxo-2,9-diphenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-6-carboxylate (1361559-68-3)

Guidance literature:

With (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; In toluene; at 20 ℃; enantioselective reaction; Inert atmosphere;

DOI:10.1002/chem.201103502

Reference yield:

benzaldehyde (100-52-7) → ethyl 4-oxo-2,9-diphenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-6-carboxylate (1361329-65-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium acetate; acetic anhydride / tetrahydrofuran / 3 h / Reflux

2: (11aR)-(+)-5,6,10,11,12,13-hexahydro-5-phenyl-4H-diindeno[7,1-cd:1,7-ef]phosphocin / dichloromethane / 8 h / 20 °C / Molecular sieve; Inert atmosphere

With (11aR)-(+)-5,6,10,11,12,13-hexahydro-5-phenyl-4H-diindeno[7,1-cd:1,7-ef]phosphocin; sodium acetate; acetic anhydride; In tetrahydrofuran; dichloromethane;

DOI:10.1039/c2cc17709a

upstream raw materials:

ethyl 2,3-butadienoate

(4Z)-4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-one

4-benzylidene-2-phenyloxazole-5(4H)-one

benzaldehyde