40918-96-5

Basic information

• Product Name: 2-Propenoic acid, 3-(1,3-benzodioxol-5-yl)-, methyl ester, (E)-
• Synonyms: 2-hydroxy-3-methoxy-trans-cinnamic acid methyl ester;methyl (2E)-3-(2-hydroxy-3-methoxyphenyl)acrylate;2-hydroxy-3-methoxy-(E)-cinnamic acid methyl ester;2-Hydroxy-3-methoxy-trans-zimtsaeure-methylester;2-Propenoic acid,3-(2-hydroxy-3-methoxyphenyl)-,methyl ester,(2E);methyl E-3-<3,4-(methylenedioxy)phenyl>acrylate;Methyl (E)-3-(3,4-methylenedioxyphenyl)propenoate;(E)-methyl 3-(benzo[d][1,3]dioxol-5-yl)acrylate;(E)-3,4-methylenedioxycinnamic acid methyl ester;(E)-methyl 3-(1,3-benzodioxol-5-yl)prop-2-enoate
• CAS NO: 40918-96-5
• Molecular Formula: C11H10O4
• Molecular Weight: 206.198
• Mol File: 40918-96-5.mol
• Article Data: 40

Chemical Properties

• CAS DataBase Reference: 2-Propenoic acid, 3-(1,3-benzodioxol-5-yl)-, methyl ester, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid, 3-(1,3-benzodioxol-5-yl)-, methyl ester, (E)-(40918-96-5)
• EPA Substance Registry System: 2-Propenoic acid, 3-(1,3-benzodioxol-5-yl)-, methyl ester, (E)-(40918-96-5)

Safety Data

• Hazardous Substances Data: 40918-96-5(Hazardous Substances Data)

Upstream product

• 120-57-0 piperonal 
• 79-20-9 acetic acid methyl ester 
• 112050-77-8 3t-benzo[1,3]dioxol-5-yl-N-phenyl-acrylimidic acid methyl ester 
• 67-56-1 methanol 
• 2373-80-0 3,4-methylenedioxy-trans-cinnamic acid 
• 20850-43-5 5-(chloromethyl)-1,3-benzodioxole 
• 14090-83-6 methyl 2-phenylsulfinylacetate 
• 75-11-6 diiodomethane 
• 3843-74-1 Methyl caffeate 
• 186581-53-3 diazomethane 
• 2635-13-4 1,2-(methylenedioxy)-4-bromobenzene 
• 292638-85-8 acrylic acid methyl ester 
• 121-69-7 N,N-dimethyl-aniline 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 58095-76-4 (E)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-ol 
• 2373-80-0 3,4-methylenedioxy-trans-cinnamic acid 
• 331-39-5 caffeic acid 
• 23512-46-1 piperanine 
• 30830-55-8 3-(3,4-methylenedioxyphenyl)propionaldehyde 
• 58095-77-5 (E)-3,4-methylenedioxycinnamaldehyde 
• 94-62-2 Piperine 
• 17301-91-6 (3R*,4R*)-3-(3,4,5-trimethoxybenzyl)-4-(3,4-methylenedioxybenzyl)-4,5-dihydro-2(3H)-furanone 
• 139448-51-4 (E)-3-(benzo[d][1,3]dioxol-5-yl)allyl 2-bromo-3-(3,4,5-trimethoxyphenyl)propanoate 
• 17301-91-6 (+/-)-cis-dihydroanhydropodorhizol 
• 247045-82-5 methyl (3S)-3-(1,3-benzodioxol-5-yl)-3-{[(4-nitrophenoxy)carbonyl]amino}propanoate 
• 57961-87-2 3-(6-bromo-1,3-benzodioxol-5-yl)propanal 
• 1448019-82-6 (3R,4R)-4-[(6-bromo-1,3-benzodioxol-5-yl)methyl]-3-[(3,4,5-trimethoxyphenyl)amino]dihydrofuran-2(3H)-one 
• 1448019-80-4 (5aS,8aR)-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydro-1,3-dioxolo[4,5-g]furo[3,4-b]quinolin-6(5aH)-one 

Relevant articles and documents

Scalable Synthesis and Cancer Cell Cytotoxicity of Rooperol and Analogues

Plant polyphenols, such as the African potato (Hypoxis hemerocallidea)-derived bis-catechol rooperol, can display promising anticancer activity yet suffer from rapid metabolism. Embarking upon a program to systematically examine potentially more metabolically stable replacements for the catechol rings in rooperol, we report here a general, scalable synthesis of rooperol and analogues that builds on our previous synthetic approach incorporating a key Pd-catalyzed decarboxylative coupling strategy. Using this approach, we have prepared and evaluated the cancer cell cytotoxicity of rooperol and a series of analogues. While none of the analogues examined here were superior to rooperol in preventing the growth of cancer cells, analogues containing phenol or methylenedioxyphenyl replacements for one or both catechol rings were nearly as effective as rooperol.

Oxoammonium-Mediated Allylsilane–Ether Coupling Reaction

A new C(sp3)?H functionalization reaction consisting of the oxidative α-allylation of allyl- and benzyl- methyl ethers has been developed. The C?C coupling could be carried out under mild conditions thanks to the use of cheap and green oxoammonium salts. The scope of the reaction was studied over 27 examples, considering the nature of the substituents on the two coupling partners.

Mizoroki-Heck Reaction of Unstrained Aryl Ketones via Ligand-Promoted C-C Bond Olefination

Mizoroki-Heck reaction of unstrained aryl ketone with acrylate/styrene is accomplished via palladium-catalyzed ligand-promoted C-C bond cleavage. Various (hetero)aryl ketones are compatible in the reaction, affording the alkene product in good to excellent yields. Further applications in the late-stage olefination of some drugs, natural products, and fragrance-derived aryl ketones demonstrate the synthetic utility of this protocol. By employing ketone as both the directing group and the leaving group, 1,2-bifunctionalization is achieved via sequential ortho-C-H alkylation/ipso-Heck olefination.