622-06-0

Basic information

• Product Name: 2-Butenedioic acid(Z)-bis(phenyl methyl)ester
• Synonyms: 2-Butenedioic acid(Z)-bis(phenyl methyl)ester;Maleic acid dibenzyl ester
• CAS NO: 622-06-0
• Molecular Formula: C₁₈H₁₆O₄
• Molecular Weight: 296.32
• Mol File: 622-06-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 420.8±25.0 °C(Predicted)
• Appearance: /
• Density: 1.187±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2-Butenedioic acid(Z)-bis(phenyl methyl)ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butenedioic acid(Z)-bis(phenyl methyl)ester(622-06-0)
• EPA Substance Registry System: 2-Butenedioic acid(Z)-bis(phenyl methyl)ester(622-06-0)

Safety Data

• Hazardous Substances Data: 622-06-0(Hazardous Substances Data)

Usage

Uses

Dibenzyl Maleate is an potential degradation product in over-the-counter phenylephrine containing drugs.

Upstream product

• 100-44-7 benzyl chloride 
• 52267-51-3 benzyl diazoacetate 
• 63254-54-6 cyclohexyl diazoacetate 
• 35059-50-8 t-butyl diazoacetate 
• 623-73-4 diazoacetic acid ethyl ester 
• 100-39-0 benzyl bromide 
• 110-16-7 maleic acid 
• 13474-68-5 benzyl hydrogen maleate 
• 100-51-6 benzyl alcohol 

Downstream Products

• 20080-27-7 3-phenyl-4,5-dihydro-isoxazole-4r,5c-dicarboxylic acid dibenzyl ester 
• 538-64-7 dibenzyl fumarate 
• 13474-68-5 Benzyl fumarate 
• 97678-47-2 2-Phenylsulfanyl-succinic acid dibenzyl ester 

Relevant articles and documents

New aziridine-based inhibitors of cathepsin L-like cysteine proteases with selectivity for the Leishmania cysteine protease LmCPB2.8

In the present work a series of aziridine-2,3-dicarboxylate inhibitors of papain-like cysteine proteases was designed, synthesized and tested. The compounds displayed selectivity for the parasitic protozoon Leishmania mexicana cathepsin L-like cysteine protease LmCPB2.8. The computational methods of homology modelling and molecular docking predicted some significant differences in the S2 pocket of LmCPB2.8 and cruzain, a related enzyme from Trypanosoma cruzi. Due to the presence of Tyr209 in LmCPB2.8 rather than Glu208 in cruzain sterically demanding, lipophilic ester groups (inhibitor 7d, 9d, 12d and 14d) are predicted to occupy the S2 pocket of the Leishmania protease, but do not form favorable interactions in cruzain, which is in common with our experimental results. Further, inhibitor 18 bearing a free carboxylic acid attached to the aziridine moiety showed a time-dependent inhibition of LmCPB2.8 (Ki = 0.41 μM; k2nd = 190,569 M?1 min?1). Docking results suggested a strong ionic interaction with the positively charged His163 of the active site. Biological and theoretical data confirm that the novel selective aziridine-based inhibitors are promising candidates for further optimization as LmCPB2.8 inhibitors.

Photoorganocatalytic synthesis of lactones: Via a selective C-H activation-alkylation of alcohols

Selective C-H activation is an area of growing importance in modern organic chemistry. Herein, we report our efforts in combining organocatalysis and photocatalysis for the development of a highly efficient and selective visible-light mediated protocol for the C-H activation and addition of various alcohols to a plethora of Michael acceptors, followed by a cyclization reaction leading to lactones, a repeatedly occurring motif in nature. Utilizing phenylglyoxylic acid as the photocatalyst and common household bulbs as the light source, we describe a versatile α-alkylation/lactonization of alcohols with α,β-unsaturated esters leading to products in excellent yields. The reaction mechanism was extensively studied.

A mild Boc deprotection and the importance of a free carboxylate

We report a facile and rapid removal of Boc protecting groups using microwave heating in H2O, with deprotection only requiring a free carboxylic acid group in the starting material. Unlike previous approaches, no additional reagents are required.