84385-05-7

Basic information

• Product Name: 2-Propenoic acid, 3-(2-methoxyphenyl)-, methyl ester, (Z)-
• CAS NO: 84385-05-7
• Molecular Formula: C11H12O3
• Molecular Weight: 192.214
• Mol File: 84385-05-7.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: 2-Propenoic acid, 3-(2-methoxyphenyl)-, methyl ester, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid, 3-(2-methoxyphenyl)-, methyl ester, (Z)-(84385-05-7)
• EPA Substance Registry System: 2-Propenoic acid, 3-(2-methoxyphenyl)-, methyl ester, (Z)-(84385-05-7)

Safety Data

• Hazardous Substances Data: 84385-05-7(Hazardous Substances Data)

Upstream product

• 91-64-5 coumarin 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 118652-92-9 (Z)-3-(2-methoxyphenyl)prop-2-enoyl chloride 
• 88738-78-7 bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate 
• 135-02-4 ortho-anisaldehyde 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 96-32-2 bromoacetic acid methyl ester 
• 612-16-8 (2-methoxyphenyl)methanol 
• 614-60-8 o-Coumaric acid 
• 98288-15-4 methyl 2-methoxycinnamate 
• 22621-54-1 2-Methoxy phenyl methylene-propanedioic acid dimethyl ester 

Downstream Products

• 98288-15-4 methyl 2-methoxycinnamate 
• 261633-61-8 methyl Z-3-(o-methoxyphenyl)-2-phenyl propenoate 
• 130228-49-8 2,3-dibromo-3-(2-methoxy-phenyl)-propionic acid methyl ester 
• 14737-91-8 (Z)-o-methoxycinnamic acid 

Relevant articles and documents

Synthesis of new 3,4-disubstituted pyrrolidines as thromboxane A2/prostaglandin H2 (TP) receptor antagonists

The synthesis and TP-receptor antagonistic activity of a series of 3,4-disubstituted pyrrolidines is described. The sulfonamide 1h was the most potent TP-receptor antagonist in this series with a pA2 value of 9.5 in isolated guinea pig trachea.

Microwave-Assisted Synthesis of Phenylpropanoids and Coumarins: Total Synthesis of Osthol

Herein we describe a one-pot microwave-assisted method for the synthesis of cinnamic acid and coumarin derivatives. The synthesis begins with an aldehyde synthon, and the chosen reaction conditions determine whether a cinnamic acid or coumarin derivative is formed. A regioselective Claisen rearrangement was also efficiently incorporated into the synthetic sequence to further increase the complexity of the product. Notably, this approach provides high product yields and selectivities without the need of a phenol protecting group.

Scope and Limitation of the Microwave-Assisted Catalytic Wittig Reaction

We have developed a microwave-assisted catalytic Wittig reaction. In this paper, we give full account of the scope and limitations of this reaction. A screening of various commercially available phosphine oxides as precatalysts revealed Bu3P=O to be the most promising candidate. We tested 10 silanes for the in situ reduction of the phosphine oxide to generate Bu3P as the actual catalyst. Different epoxides were tested as masked bases. In this context, cyclohexene oxide as well as butylene oxide proved to be suitable. The reaction could be carried out at 125 C, but higher yields and E/Z selectivities were obtained at 150 °C. Under the optimised reaction conditions, more than 40 examples for the conversion of various aldehydes into the corresponding alkenes are reported. The products were obtained in yields of up to 88 with high E selectivities. Moreover, we also describe the further screening of several chiral phosphines as catalysts for the microwave-assisted enantioselective catalytic Wittig reaction. The scope and limitations of the microwave-assisted catalytic Wittig reaction have been evaluated with respect to the catalyst, silane, solvent, reaction conditions, and substrates.