(Z)-3-[(R)-p-tolylsulfinyl]propenonitrile

Base Information

• Chemical Name: (Z)-3-[(R)-p-tolylsulfinyl]propenonitrile
• CAS No.: 205251-17-8
• Molecular Formula: C₁₀H₉NOS
• Molecular Weight: 191.254
• Mol file: 205251-17-8.mol

Synonyms:(Z)-3-[(R)-p-tolylsulfinyl]propenonitrile

Chemical Property of (Z)-3-[(R)-p-tolylsulfinyl]propenonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (Z)-3-[(R)-p-tolylsulfinyl]propenonitrile

There total 4 articles about (Z)-3-[(R)-p-tolylsulfinyl]propenonitrile 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: 55.0%

diethylaluminium cyanide (5804-85-3) + (+)-(R)S-ethynyl-p-tolylsulfoxide (99930-83-3) → (Z)-3-[(R)-p-tolylsulfinyl]propenonitrile (205251-17-8) + (-)-(R,R,Z)-1,2-bis(p-tolylsulfinyl)ethene

Guidance literature:

In toluene; at -20 ℃; for 0.05h; Yields of byproduct given;

DOI:10.1021/jo9721002

Reference yield: 26.0%

(+)-(R)S-ethynyl-p-tolylsulfoxide (99930-83-3) → (Z)-3-[(R)-p-tolylsulfinyl]propenonitrile (205251-17-8) + (-)-(R,R,Z)-1,2-bis(p-tolylsulfinyl)ethene

Guidance literature:

With diethylaluminium cyanide; In toluene; at -78 ℃; for 24h;

DOI:10.1021/jo9721002

Reference yield:

2-isopropyl-5-methylcyclohexyl 4-methylbenzenesulfinate (98147-48-9) → (Z)-3-[(R)-p-tolylsulfinyl]propenonitrile (205251-17-8)

Guidance literature:

Multi-step reaction with 2 steps

1: EtMgBr / diethyl ether

2: toluene

With ethylmagnesium bromide; In diethyl ether; toluene;

DOI:10.1021/ol016481o

upstream raw materials:

diethylaluminium cyanide

(+)-(R)_S-ethynyl-p-tolylsulfoxide

(R)-ethynyl-p-tolyl-sulfoxide

2-isopropyl-5-methylcyclohexyl 4-methylbenzenesulfinate

Downstream raw materials:

C₂₃H₂₂N₂O₃S

C₂₃H₂₂N₂O₃S

Ethyl 1-cyanopyrrolo<5,1-a>isoquinoline-3-carboxylate

ethyl [5S,6R,7S,7aS,S(R)]-2-[2-(acetyloxy)ethyl]-7-cyano-3-methyl-6-(p-tolylsulfinyl)-5,6,7,7a-tetrahydropyrrolo[2,1-b][1,3]thiazole-5-carboxylate

Refernces

• 1、 Garci?a Ruano, Jose L.,Gamboa, Antonio Esteban,Marti?n Castro, Ana M.,Rodri?guez, Jesu?s H.,Lo?pez-Solera, M. Isabel. "Synthesis and Dienophilic Behavior of Enantiomerically Pure (Z)-3-p-Tolylsulfinylacrylonitriles". . p. 3324 - 3332. Retrieved 2007/10/03.