(+/-)-(Z)-3-[4-hydroxy-4-(4-nitrophenyl)butan-2-ylidene]-1-(methoxycarbonyl)indolin-2-one

Base Information

• Chemical Name: (+/-)-(Z)-3-[4-hydroxy-4-(4-nitrophenyl)butan-2-ylidene]-1-(methoxycarbonyl)indolin-2-one
• CAS No.: 1374606-06-0
• Molecular Formula: C₂₀H₁₈N₂O₆
• Molecular Weight: 382.373
• Mol file: 1374606-06-0.mol

Synonyms:(+/-)-(Z)-3-[4-hydroxy-4-(4-nitrophenyl)butan-2-ylidene]-1-(methoxycarbonyl)indolin-2-one

Chemical Property of (+/-)-(Z)-3-[4-hydroxy-4-(4-nitrophenyl)butan-2-ylidene]-1-(methoxycarbonyl)indolin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-(Z)-3-[4-hydroxy-4-(4-nitrophenyl)butan-2-ylidene]-1-(methoxycarbonyl)indolin-2-one

There total 4 articles about (+/-)-(Z)-3-[4-hydroxy-4-(4-nitrophenyl)butan-2-ylidene]-1-(methoxycarbonyl)indolin-2-one 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: 60.0%

2-[(tert-butyldimethylsilyl)oxy]-1-(methoxycarbonyl)-3-(prop-1-en-2-yl)-1H-indole (1374605-99-8) + 4-nitrobenzaldehdye (555-16-8) → (+/-)-(Z)-3-[4-hydroxy-4-(4-nitrophenyl)butan-2-ylidene]-1-(methoxycarbonyl)indolin-2-one (1374606-06-0)

Guidance literature:

With tetrachlorosilane; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; at -20 ℃; for 12h; optical yield given as %de; Inert atmosphere;

DOI:10.1002/ejoc.201101446

Reference yield:

methyl 3-(1-methylethylidene)-2-oxo-2,3-dihydro-1H-indole-1-carboxylate (957136-96-8) → (+/-)-(Z)-3-[4-hydroxy-4-(4-nitrophenyl)butan-2-ylidene]-1-(methoxycarbonyl)indolin-2-one (1374606-06-0)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere; Cooling

2: tetrachlorosilane; N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 12 h / -20 °C / Inert atmosphere

With tetrachlorosilane; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; 2: Mukaiyama aldol reaction;

DOI:10.1002/ejoc.201101446

Reference yield:

2-oxoindole (59-48-3) → (+/-)-(Z)-3-[4-hydroxy-4-(4-nitrophenyl)butan-2-ylidene]-1-(methoxycarbonyl)indolin-2-one (1374606-06-0)

Guidance literature:

Multi-step reaction with 4 steps

1: piperidine / ethanol / 4 h / 23 °C / Inert atmosphere

2: dmap / acetonitrile / 2 h / 20 °C / Inert atmosphere

3: triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere; Cooling

4: tetrachlorosilane; N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 12 h / -20 °C / Inert atmosphere

With piperidine; dmap; tetrachlorosilane; triethylamine; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 4: Mukaiyama aldol reaction;

DOI:10.1002/ejoc.201101446

upstream raw materials:

methyl 3-(1-methylethylidene)-2-oxo-2,3-dihydro-1H-indole-1-carboxylate

2-oxoindole

3-Isopropylidene-1,3-dihydro-indol-2-one

2-[(tert-butyldimethylsilyl)oxy]-1-(methoxycarbonyl)-3-(prop-1-en-2-yl)-1H-indole