1397699-67-0

Basic information

• Product Name: (S,E)-1-((4-cyclohexylbut-3-en-2-yl)sulfonyl)-4-methylbenzene
• Synonyms: (S,E)-1-((4-cyclohexylbut-3-en-2-yl)sulfonyl)-4-methylbenzene
• CAS NO: 1397699-67-0
• Molecular Weight: 292.442
• Mol File: 1397699-67-0.mol

Chemical Properties

• CAS DataBase Reference: (S,E)-1-((4-cyclohexylbut-3-en-2-yl)sulfonyl)-4-methylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: (S,E)-1-((4-cyclohexylbut-3-en-2-yl)sulfonyl)-4-methylbenzene(1397699-67-0)
• EPA Substance Registry System: (S,E)-1-((4-cyclohexylbut-3-en-2-yl)sulfonyl)-4-methylbenzene(1397699-67-0)

Safety Data

• Hazardous Substances Data: 1397699-67-0(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 25203-83-2 (E)-1-cyclohexyl-1,3-butadiene 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 2043-61-0 cyclohexanecarbaldehyde 
• 1397700-06-9 C₁₀H₁₇NO 
• 1397699-99-8 C₁₀H₁₉N 
• 824-79-3 sodium 4-methylbenzenesulfinate 

Relevant articles and documents

Palladium-Catalyzed Asymmetric Hydrosulfonylation of 1,3-Dienes with Sulfonyl Hydrazides

A highly enantio- and regioselective hydrosulfonylation of 1,3-dienes with sulfonyl hydrazides has been realized by using a palladium catalyst containing a monodentate chiral spiro phosphoramidite ligand. The reaction provided an efficient approach to synthetically useful chiral allylic sulfones. Mechanistic studies suggest that the reaction proceeds through the formation of an allyl hydrazine intermediate and subsequent rearrangement to the chiral allylic sulfone product. The transformation of the allyl hydrazine intermediate to the product is the enantioselectivity-determining step.

Direct substitution of primary allylic amines with sulfinate salts

The NH2 group in primary allylic amines was substituted directly by sulfinate salts with excellent regio- and stereoselectivities. In the presence of 0.1 mol % [Pd(allyl)Cl]2, 0.4 mol % 1,4- bis(diphenylphosphino)butane (dppb), and excess boric acid, a range of α-unbranched primary allylic amines were smoothly substituted with sodium sulfinates in an α-selective fashion to give structurally diverse allylic sulfones in good to excellent yields with exclusive E selectivity. Replacing dppb with 1,1′-bi-2-naphthol (BINOL) allowed unsymmetric α-chiral primary allylic amines to be transformed into the corresponding allylic sulfones in good to excellent yields with excellent retention of ee. Importantly, the reaction complements known asymmetric methods in substrate scope via its unique ability to provide α-chiral allylic sulfones with high optical purity starting from unsymmetric allylic electrophiles.