[2S,(S)S]-2-(prop-2-ynyl)-2-[2-(p-tolylsulfinyl)-phenyl]pent-4-enenitrile

Base Information

Chemical Name:[2S,(S)S]-2-(prop-2-ynyl)-2-[2-(p-tolylsulfinyl)-phenyl]pent-4-enenitrile
CAS No.:1392203-76-7
Molecular Formula:C₂₁H₁₉NOS
Molecular Weight:333.454
Hs Code.:

Synonyms:[2S,(S)S]-2-(prop-2-ynyl)-2-[2-(p-tolylsulfinyl)-phenyl]pent-4-enenitrile

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Chemical Property of [2S,(S)S]-2-(prop-2-ynyl)-2-[2-(p-tolylsulfinyl)-phenyl]pent-4-enenitrile

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Technology Process of [2S,(S)S]-2-(prop-2-ynyl)-2-[2-(p-tolylsulfinyl)-phenyl]pent-4-enenitrile

There total 2 articles about [2S,(S)S]-2-(prop-2-ynyl)-2-[2-(p-tolylsulfinyl)-phenyl]pent-4-enenitrile 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: 62.0%

: [(S)S]-2-[2-(p-tolylsulfinyl)phenyl]pent-4-enenitrile

: 106-96-7
propargyl bromide

: 1392203-75-6
[2R,(S)S]-2-(prop-2-ynyl)-2-[2-(p-tolylsulfinyl)-phenyl]pent-4-enenitrile

: 1392203-76-7
[2S,(S)S]-2-(prop-2-ynyl)-2-[2-(p-tolylsulfinyl)-phenyl]pent-4-enenitrile

Guidance literature:: [(S)S]-2-[2-(p-tolylsulfinyl)phenyl]pent-4-enenitrile; With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.166667h; Inert atmosphere;

propargyl bromide; In tetrahydrofuran; toluene; at -78 ℃; for 1h; optical yield given as %de; stereoselective reaction; Inert atmosphere;
DOI:10.1021/jo3011039

Reference yield:

: 1286196-72-2
(S)-2-[2-(p-tolylsulfinyl)phenyl]acetonitrile

: 1392203-76-7
[2S,(S)S]-2-(prop-2-ynyl)-2-[2-(p-tolylsulfinyl)-phenyl]pent-4-enenitrile

Guidance literature:: Multi-step reaction with 2 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

1.2: 0.17 h / 20 °C / Inert atmosphere

2.1: 18-crown-6 ether; sodium hexamethyldisilazane / tetrahydrofuran; toluene / 0.17 h / -78 °C / Inert atmosphere

2.2: -78 °C / Inert atmosphere

With 18-crown-6 ether; sodium hexamethyldisilazane; lithium hexamethyldisilazane; In tetrahydrofuran; toluene;
DOI:10.1021/jo3011039

Reference yield: 58.0%

: 1392203-76-7
[2S,(S)S]-2-(prop-2-ynyl)-2-[2-(p-tolylsulfinyl)-phenyl]pent-4-enenitrile

: 1392204-47-5
(S)-2-(prop-2-ynyl)-2-[2-(p-tolylsulfenyl)phenyl]pent-4-enamide

Guidance literature:: [2S,(S)S]-2-(prop-2-ynyl)-2-[2-(p-tolylsulfinyl)-phenyl]pent-4-enenitrile; With boron trifluoride diethyl etherate; In acetonitrile; at 20 ℃; for 0.5h; Inert atmosphere;

With sodium iodide; In acetonitrile; at 20 ℃; for 4.5h; optical yield given as %ee; Inert atmosphere;
DOI:10.1021/jo3011039