endo-<4aR,5R,8S,8aR,(S)S>-5,8-methano-2-(p-tolylsulfinyl)-4a,5,8,8a-tetrahydro-1,4-naphthoquinone

Base Information

Chemical Name:endo-<4aR,5R,8S,8aR,(S)S>-5,8-methano-2-(p-tolylsulfinyl)-4a,5,8,8a-tetrahydro-1,4-naphthoquinone
CAS No.:174060-78-7
Molecular Formula:C₁₈H₁₆O₃S
Molecular Weight:312.389
Hs Code.:

Synonyms:endo-<4aR,5R,8S,8aR,(S)S>-5,8-methano-2-(p-tolylsulfinyl)-4a,5,8,8a-tetrahydro-1,4-naphthoquinone

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Chemical Property of endo-<4aR,5R,8S,8aR,(S)S>-5,8-methano-2-(p-tolylsulfinyl)-4a,5,8,8a-tetrahydro-1,4-naphthoquinone

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Technology Process of endo-<4aR,5R,8S,8aR,(S)S>-5,8-methano-2-(p-tolylsulfinyl)-4a,5,8,8a-tetrahydro-1,4-naphthoquinone

There total 3 articles about endo-<4aR,5R,8S,8aR,(S)S>-5,8-methano-2-(p-tolylsulfinyl)-4a,5,8,8a-tetrahydro-1,4-naphthoquinone 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: 72.0%

: 134281-83-7
(+)-(S)-2-(p-tolylsulfinyl)cyclohexa-2,5-diene-1,4-dione

: 542-92-7,25568-84-7,7313-32-8
cyclopenta-1,3-diene

: 162060-46-0
endo-<4aR,5S,8R,8aS,(S)S>-5,8-methano-2-(p-tolylsulfinyl)-4a,5,8,8a-tetrahydro-1,4-naphthoquinone

: 174060-78-7
endo-<4aR,5R,8S,8aR,(S)S>-5,8-methano-2-(p-tolylsulfinyl)-4a,5,8,8a-tetrahydro-1,4-naphthoquinone

Guidance literature:: In chloroform; at -20 ℃; Product distribution; effect of solvent, temperature and catalyst;
DOI:10.1016/S0040-4039(00)99307-9

Reference yield:

: 134281-83-7
(+)-(S)-2-(p-tolylsulfinyl)cyclohexa-2,5-diene-1,4-dione

: 542-92-7,25568-84-7,7313-32-8
cyclopenta-1,3-diene

: 162060-46-0
endo-<4aR,5S,8R,8aS,(S)S>-5,8-methano-2-(p-tolylsulfinyl)-4a,5,8,8a-tetrahydro-1,4-naphthoquinone

: 174060-78-7
endo-<4aR,5R,8S,8aR,(S)S>-5,8-methano-2-(p-tolylsulfinyl)-4a,5,8,8a-tetrahydro-1,4-naphthoquinone

: (1R,4S,4aS,8aR)-4a-((S)-Toluene-4-sulfinyl)-1,4,4a,8a-tetrahydro-1,4-methano-naphthalene-5,8-dione

Guidance literature:: With Eu(fod)3; In dichloromethane; at -20 ℃; for 0.5h;
DOI:10.1021/jo9913107

Reference yield:

: 134281-83-7
(+)-(S)-2-(p-tolylsulfinyl)cyclohexa-2,5-diene-1,4-dione

: 542-92-7,25568-84-7,7313-32-8
cyclopenta-1,3-diene

: 162060-46-0
endo-<4aR,5S,8R,8aS,(S)S>-5,8-methano-2-(p-tolylsulfinyl)-4a,5,8,8a-tetrahydro-1,4-naphthoquinone

: 174060-78-7
endo-<4aR,5R,8S,8aR,(S)S>-5,8-methano-2-(p-tolylsulfinyl)-4a,5,8,8a-tetrahydro-1,4-naphthoquinone

: endo-<4aS,5S,8R,8aR,(S)S>-5,8-methano-2-(p-tolylsulfinyl)-4a,5,8,8a-tetrahydro-1,4-naphthoquinone

Guidance literature:: With zinc dibromide; In dichloromethane; for 0.05h; Product distribution; Ambient temperature; Diels-Alder reactions with cyclic and acyclic dienes; influence of the sulfinyl group on the chemoselectivity and ?-facial selectivity; diastereomeric excess; effect of reaction conditions (solvent, temperature, time, presence of Lewis acids);
DOI:10.1021/jo951438y