200720-85-0

Basic information

• Product Name: (E)-(S)-3-(4-Chloro-phenyl)-hex-4-enoic acid ethyl ester
• Synonyms: (E)-(S)-3-(4-Chloro-phenyl)-hex-4-enoic acid ethyl ester
• CAS NO: 200720-85-0
• Molecular Weight: 252.741
• Mol File: 200720-85-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (E)-(S)-3-(4-Chloro-phenyl)-hex-4-enoic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-(S)-3-(4-Chloro-phenyl)-hex-4-enoic acid ethyl ester(200720-85-0)
• EPA Substance Registry System: (E)-(S)-3-(4-Chloro-phenyl)-hex-4-enoic acid ethyl ester(200720-85-0)

Safety Data

• Hazardous Substances Data: 200720-85-0(Hazardous Substances Data)

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 32271-56-0 (E)-4-(4-chlorophenyl)but-3-en-2-ol 
• 331866-60-5 (2R,3E)-4-(4-chlorophenyl)-3-buten-2-ol 
• 30626-03-0 (3E)-4-(4-chlorophenyl)-3-buten-2-one 
• 78-39-7 Triethyl orthoacetate 
• 200720-81-6 (E)-(S)-4-(4-chlorophenyl)but-3-en-2-ol 

Downstream Products

• 578731-46-1 3-(4-chlorophenyl)hexanoate 
• 69308-37-8 (R)-baclofen 

Relevant articles and documents

Diastereoselective rhodium(II)-catalyzed sulfonium ylide formation-[2,3]-sigmatropic rearrangement reaction of chiral non-racemic allylic sulfides

The tandem sulfonium ylide formation-[2,3]-sigmatropic rearrangement reaction of chiral non-racemic secondary allylic sulfides, (E)-9 and (Z)-10, is found to proceed with high diastereocontrol. The C-5 stereocenter bearing the sulfide group is essential for high diastereoselectivity in the reaction. Transition state conformers are proposed to explain the high diastereoselectivity in the formation of the diastereomeric products, 18a and 18b. The method is applied to the synthesis of (R)-4-(4-chlorophenyl)-2-butyrolactone. Modest enantioselectivity (63% ee) was achieved and this is attributed to partial racemization during the formation of the secondary allylic sulfide 22.