(1S,2S,4R)-7,7-dimethyl-1-[(E)-2-(phenylthio)vinyl]-2-[(Z)-1-propenyl]bicyclo[2.2.1]heptan-2-ol

Base Information

Chemical Name:(1S,2S,4R)-7,7-dimethyl-1-[(E)-2-(phenylthio)vinyl]-2-[(Z)-1-propenyl]bicyclo[2.2.1]heptan-2-ol
CAS No.:308122-91-0
Molecular Formula:C₂₀H₂₆OS
Molecular Weight:314.492
Hs Code.:

Synonyms:(1S,2S,4R)-7,7-dimethyl-1-[(E)-2-(phenylthio)vinyl]-2-[(Z)-1-propenyl]bicyclo[2.2.1]heptan-2-ol

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Chemical Property of (1S,2S,4R)-7,7-dimethyl-1-[(E)-2-(phenylthio)vinyl]-2-[(Z)-1-propenyl]bicyclo[2.2.1]heptan-2-ol

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Technology Process of (1S,2S,4R)-7,7-dimethyl-1-[(E)-2-(phenylthio)vinyl]-2-[(Z)-1-propenyl]bicyclo[2.2.1]heptan-2-ol

There total 3 articles about (1S,2S,4R)-7,7-dimethyl-1-[(E)-2-(phenylthio)vinyl]-2-[(Z)-1-propenyl]bicyclo[2.2.1]heptan-2-ol 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: 32.0%

: 13154-14-8
(Z)-1-propenylmagnesium bromide

: (1S,4R)-7,7-dimethyl-1-[(E)-2-(phenylthio)vinyl]-2-norbornanone

: 308122-91-0
(1S,2S,4R)-7,7-dimethyl-1-[(E)-2-(phenylthio)vinyl]-2-[(Z)-1-propenyl]bicyclo[2.2.1]heptan-2-ol

Guidance literature:: (Z)-1-propenylmagnesium bromide; With cerium(III) chloride; tert.-butyl lithium; In tetrahydrofuran; at -78 ℃; for 1h;

(1S,4R)-7,7-dimethyl-1-[(E)-2-(phenylthio)vinyl]-2-norbornanone; In tetrahydrofuran; at -78 ℃; for 2.5h; Further stages.;
DOI:10.1021/ja0025402

Reference yield:

: 86023-73-6,6004-71-3
7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-carbaldehyde

: 308122-91-0
(1S,2S,4R)-7,7-dimethyl-1-[(E)-2-(phenylthio)vinyl]-2-[(Z)-1-propenyl]bicyclo[2.2.1]heptan-2-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium hexamethyldisilazide / tetrahydrofuran / 0.75 h / 0 °C

1.2: tetrahydrofuran / 2 h

2.1: CeCl₃; tert-butyllithium / tetrahydrofuran / 1 h / -78 °C

2.2: 32 percent / tetrahydrofuran / 2.5 h / -78 °C

With cerium(III) chloride; tert.-butyl lithium; potassium hexamethylsilazane; In tetrahydrofuran; 1.2: Wittig olefination;
DOI:10.1021/ja0025402

Reference yield:

: 13884-92-9
phenylthiomethyl triphenylphosphonium chloride

: 308122-91-0
(1S,2S,4R)-7,7-dimethyl-1-[(E)-2-(phenylthio)vinyl]-2-[(Z)-1-propenyl]bicyclo[2.2.1]heptan-2-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium hexamethyldisilazide / tetrahydrofuran / 0.75 h / 0 °C

1.2: tetrahydrofuran / 2 h

2.1: CeCl₃; tert-butyllithium / tetrahydrofuran / 1 h / -78 °C

2.2: 32 percent / tetrahydrofuran / 2.5 h / -78 °C

With cerium(III) chloride; tert.-butyl lithium; potassium hexamethylsilazane; In tetrahydrofuran; 1.2: Wittig olefination;
DOI:10.1021/ja0025402