(Z)-dimethyl 2-(allylimino)-5-(1-tosyl-1H-indol-3-yl)dihydrothiophene-3,3(2H)-dicarboxylate

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Chemical Name:(Z)-dimethyl 2-(allylimino)-5-(1-tosyl-1H-indol-3-yl)dihydrothiophene-3,3(2H)-dicarboxylate
CAS No.:1402823-90-8
Molecular Formula:C₂₆H₂₆N₂O₆S₂
Molecular Weight:526.634
Hs Code.:

Synonyms:(Z)-dimethyl 2-(allylimino)-5-(1-tosyl-1H-indol-3-yl)dihydrothiophene-3,3(2H)-dicarboxylate

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Chemical Property of (Z)-dimethyl 2-(allylimino)-5-(1-tosyl-1H-indol-3-yl)dihydrothiophene-3,3(2H)-dicarboxylate

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Technology Process of (Z)-dimethyl 2-(allylimino)-5-(1-tosyl-1H-indol-3-yl)dihydrothiophene-3,3(2H)-dicarboxylate

There total 3 articles about (Z)-dimethyl 2-(allylimino)-5-(1-tosyl-1H-indol-3-yl)dihydrothiophene-3,3(2H)-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: 77.0%

: 1181824-71-4
dimethyl 2-[1-(4-toluenesulfonyl)-1H-indol-3-yl]cyclopropane-1,1-dicarboxylate

: 57-06-7,58391-87-0
N-allyl isothiocyanate

: 1402823-90-8
(Z)-dimethyl 2-(allylimino)-5-(1-tosyl-1H-indol-3-yl)dihydrothiophene-3,3(2H)-dicarboxylate

Guidance literature:: With tin(II) trifluoromethanesulfonate; In dichloromethane; at 23 ℃; for 1.5h; chemoselective reaction; Inert atmosphere; Glovebox;
DOI:10.1021/ol302494n DOI:10.1021/ol302494n

Reference yield:

: 50562-79-3
1-(4-tolylsulfonyl)indole-3-carboxaldehyde

: 1402823-90-8
(Z)-dimethyl 2-(allylimino)-5-(1-tosyl-1H-indol-3-yl)dihydrothiophene-3,3(2H)-dicarboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: piperidine; acetic acid / benzene / Dean-Stark; Reflux; Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 22 °C / Inert atmosphere

2.2: 22 °C / Inert atmosphere

3.1: tin(II) trifluoromethanesulfonate / dichloromethane / 1.5 h / 23 °C / Inert atmosphere; Glovebox

With piperidine; tin(II) trifluoromethanesulfonate; sodium hydride; acetic acid; In dichloromethane; N,N-dimethyl-formamide; benzene; 1.1: |Knoevenagel Condensation / 2.1: |Johnson-Corey-Chaykovsky Reaction / 2.2: |Johnson-Corey-Chaykovsky Reaction;
DOI:10.1021/ol302494n DOI:10.1021/ol302494n

Reference yield:

: methyl 4-(N-p-toluenesulfonyl-3-indolyl)-3-carbomethoxybutenoate

: 1402823-90-8
(Z)-dimethyl 2-(allylimino)-5-(1-tosyl-1H-indol-3-yl)dihydrothiophene-3,3(2H)-dicarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 22 °C / Inert atmosphere

1.2: 22 °C / Inert atmosphere

2.1: tin(II) trifluoromethanesulfonate / dichloromethane / 1.5 h / 23 °C / Inert atmosphere; Glovebox

With tin(II) trifluoromethanesulfonate; sodium hydride; In dichloromethane; N,N-dimethyl-formamide; 1.1: |Johnson-Corey-Chaykovsky Reaction / 1.2: |Johnson-Corey-Chaykovsky Reaction;
DOI:10.1021/ol302494n DOI:10.1021/ol302494n