ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)cyclohexa-1,3-dienecarboxylate

Base Information

Chemical Name:ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)cyclohexa-1,3-dienecarboxylate
CAS No.:1041262-64-9
Molecular Formula:C₁₇H₁₅NO₄
Molecular Weight:297.31
Hs Code.:

Synonyms:ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)cyclohexa-1,3-dienecarboxylate

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Chemical Property of ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)cyclohexa-1,3-dienecarboxylate

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Technology Process of ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)cyclohexa-1,3-dienecarboxylate

There total 5 articles about ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)cyclohexa-1,3-dienecarboxylate 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:

: 1041262-63-8
ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)-1-(phenylthio)cyclohex-3-enecarboxylate

: 1041262-64-9
ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)cyclohexa-1,3-dienecarboxylate

: ethyl (3S)-3-(1,3-dioxoisoindolin-2-yl)cyclohexa-1,4-dienecarboxylate

Guidance literature:: ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)-1-(phenylthio)cyclohex-3-enecarboxylate; With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In toluene; at 0 ℃; for 2h;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 60 ℃; for 5h; Further stages. Title compound not separated from byproducts.;
DOI:10.1002/anie.200800282

Reference yield:

: 1291090-01-1
C₂₃H₂₁NO₄Se

: 1041262-64-9
ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)cyclohexa-1,3-dienecarboxylate

: ethyl (3S)-3-(1,3-dioxoisoindolin-2-yl)cyclohexa-1,4-dienecarboxylate

Guidance literature:: With pyridine; dihydrogen peroxide; In tetrahydrofuran; water; at 0 - 20 ℃; for 3h; Overall yield = 96 percent; Overall yield = 114 mg;
DOI:10.1021/acs.joc.1c00326

Reference yield:

: 4720-83-6
6-oxabicyclo<3.2.1>-oct-3-en-7-one

: 1041262-64-9
ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)cyclohexa-1,3-dienecarboxylate

: ethyl (3S)-3-(1,3-dioxoisoindolin-2-yl)cyclohexa-1,4-dienecarboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: bis(η3-allyl-μ-chloropalladium(II)); (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane / tetrahydrofuran / 0.33 h / 40 °C / Inert atmosphere

1.2: 8 h / 40 °C / Inert atmosphere

1.3: 10 h / Inert atmosphere; Reflux

2.1: potassium hexamethylsilazane / tetrahydrofuran / 6 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / toluene / 2 h / 0 °C / Inert atmosphere

3.2: 5 h / 60 °C / Inert atmosphere

With bis(η3-allyl-μ-chloropalladium(II)); potassium hexamethylsilazane; sodium hydrogencarbonate; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; toluene;
DOI:10.1002/chem.201003454