137744-79-7

Basic information

• Product Name: 3-Butenoic acid, 4-(3,4,5-trimethoxyphenyl)-, methyl ester
• CAS NO: 137744-79-7
• Molecular Formula: C14H18O5
• Molecular Weight: 266.294
• Mol File: 137744-79-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3-Butenoic acid, 4-(3,4,5-trimethoxyphenyl)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Butenoic acid, 4-(3,4,5-trimethoxyphenyl)-, methyl ester(137744-79-7)
• EPA Substance Registry System: 3-Butenoic acid, 4-(3,4,5-trimethoxyphenyl)-, methyl ester(137744-79-7)

Safety Data

• Hazardous Substances Data: 137744-79-7(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 107-93-7 (E)-but-2-enoic acid 
• 2675-79-8 1-bromo-3,4,5-trimethoxybenzene 
• 127404-78-8 4-(3,4,5-trimethoxy-phenyl)-but-3-enoic acid 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 5320-31-0 3,4,5-trimethoxyphenylacetaldehyde 
• 186581-53-3 diazomethane 

Downstream Products

• 187950-51-2 (E)-2-Diazo-4-(3,4,5-trimethoxy-phenyl)-but-3-enoic acid methyl ester 

Relevant articles and documents

Enantioselective Total Synthesis of (+)-Monocerin, a Dihydroisocoumarin Derivative with Potent Antimalarial Properties

We describe here the enantioselective synthesis of (+)-monocerin and its acetate derivative. The present synthesis features an efficient optically active synthesis of the β-hydroxy-?-lactone derivative with high enantiomeric purity using Sharpless dihydroxylation as the key step. The synthesis also highlights a tandem Lewis acid-catalyzed, oxocarbenium ion-mediated diastereoselective syn-allylation reaction, and a methoxymethyl group promoted methylenation reaction. We investigated this reaction with a variety of Lewis acids. A selective CrO3-mediated oxidation of isochroman provided the corresponding lactone derivative. The synthesis is quite efficient and may be useful for the preparation of derivatives.

Reaction of 2-Butenoic Acid Dianion and Its N-(4-Methoxyphenyl)amide with Methoxy-Substituted Arynes

N-(4-Methoxyphenyl)-1-butenamide dianion (6), generated by the reaction of N-(4-methoxyphenyl)-2-butenamide (3) with LDA or LTMP, undergoes exclusive 4-arylation with various methoxy-substituted arynes 2a-e yielding mixtures consisting of a N-(4-methoxyphenyl)-(E)-4-aryl-3-butenamide (9) (85-90percent) and a N-(4-methoxyphenyl)-(E)-4-aryl-2-butenamide 9' (10-15percent).Under certain conditions, 4,4-diarylated products 12 are also obtained. 2-Butenoic acid dianion (14) also reacts with methoxy-substituted arynes affording predominantly 4-aryl-3-butenoic acids 15 and minor amountsof 4-aryl-2-butenoic acids 15'.The exclusive low temperature (-30 to -40 deg C) 4-addition of arynes to dianion 14 is in contrast to the predominant 2-addition that 14 undergoes with certain aldehydes and ketones at comparable temperatures.The mixtures of 4-arylbutenoic acids 15 and 15' and 4-arylbutenamides 9 and 9' were readily hydrogenated (Pd/C) and esterified (MeOH/H2SO4) to synthetically valuable methyl 4-arylbutanoates 17.