75463-68-2

Basic information

• Product Name: methyl (3Z,5E)-3-methyl-6-phenylhexa-3,5-dienoate
• CAS NO: 75463-68-2
• Molecular Weight: 216.28
• Mol File: 75463-68-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: methyl (3Z,5E)-3-methyl-6-phenylhexa-3,5-dienoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (3Z,5E)-3-methyl-6-phenylhexa-3,5-dienoate(75463-68-2)
• EPA Substance Registry System: methyl (3Z,5E)-3-methyl-6-phenylhexa-3,5-dienoate(75463-68-2)

Safety Data

• Hazardous Substances Data: 75463-68-2(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 1306616-02-3 (3Z,5E)-3-methyl-6-phenylhexa-3,5-dienoic acid 
• 1118759-61-7 (E,E)-2-[2-(tert-butyldimethylsilyloxy)ethyl]-5-phenylpenta-2,4-dien-1-al 
• 1118759-64-0 (2E,4E)-2-(2-tert-butyldimethylsilyloxyethyl)-5-phenylpenta-2,4-dien-1-ol 
• 1118759-67-3 (1E,3Z)-6-tert-butyldimethylsilyloxy-4-methyl-1-phenylhexa-1,3-diene 
• 1227391-15-2 (E,E)-2-[2-(4-methoxybenzyloxy)ethyl]-5-phenylpenta-2,4-dien-1-al 
• 131938-58-4 (3Z,5E)-3-methyl-6-phenylhexa-3,5-dien-1-ol 
• 1306615-80-4 (2E,4E)-2-[2-(4-methoxybenzyloxy)ethyl]-5-phenylpenta-2,4-dien-1-ol 
• 1306615-83-7 (1E,3Z)-6-(4-methoxybenzyloxy)-4-methyl-1-phenylhexa-1,3-diene 
• 1306615-97-3 (3Z,5E)-3-methyl-6-phenylhexa-3,5-dienal 
• 16721-45-2 triphenyl(phenylmethylene)phosphorane 
• 55815-92-4 2-Methyl-2-((E)-3-phenyl-allyl)-[1,3]dioxolane 
• 42762-56-1 (E)-5-phenylpent-4-en-2-one 
• 1449-46-3 benzyltriphenylphosphonium bromide 

Downstream Products

• 52110-55-1 methyl (2E,3Z,5E)-2-(methoxymethylene)-3-methyl-6-phenylhexa-3,5-dienoate 
• 52110-55-1 (3Z,5E)-2-[1-Methoxy-meth-(E)-ylidene]-3-methyl-6-phenyl-hexa-3,5-dienoic acid methyl ester 

Relevant articles and documents

Formal synthesis of strobilurins A and X

Known synthetic precursors of strobilurins A and X, i.e., methyl (3Z,5E)-6-aryl-3-methylhexa-3,5-dienoates (aryl is phenyl, 4-methoxyphenyl), were synthesized by highly stereospecific reactions from 2-(2-tert- butyldimethylsilyloxyethyl)- and 2-[2-(4-methoxybenzyloxy)-ethyl]-5-arylpenta- 2E,4E-dien-1-ols. These dienols were efficiently dehydroxylated to (1E,3Z)-4-methyl-6-(4-methoxybenzyloxy)hexa-1,3-dienylarenes with their subsequent demethoxyben-zylation to (3Z,5E)-6-aryl-3-methylhexa-3,5-dien-1-ols. The latter through the step of corresponding aryldienals and aryldienoic acids were transformed to the target methyl (3Z,5E)-6-aryl-3-methylhexa-3,5-dienoates, which completes a formal synthesis of strobilurins A and X. Configuration of the C=C bonds of the conjugated aryldiene system is preserved in the considered transformations by 95-97%.