7028-47-9

Basic information

• Product Name: meso-3,4-diphenyladipic acid dimethyl ester
• Synonyms: meso-3,4-diphenyladipic acid dimethyl ester
• CAS NO: 7028-47-9
• Molecular Weight: 326.392
• Mol File: 7028-47-9.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: meso-3,4-diphenyladipic acid dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: meso-3,4-diphenyladipic acid dimethyl ester(7028-47-9)
• EPA Substance Registry System: meso-3,4-diphenyladipic acid dimethyl ester(7028-47-9)

Safety Data

• Hazardous Substances Data: 7028-47-9(Hazardous Substances Data)

Upstream product

• 613-90-1 benzoyl cyanide 
• 1122-62-9 2-acetylpyridine 
• 98-86-2 acetophenone 
• 623-91-6 diethyl Fumarate 
• 4192-77-2 ethyl cinnamate 
• 103-26-4 methyl cinnamate 
• 103-26-4 Methyl cinnamate 
• 67-56-1 methanol 
• 14990-09-1 tert-butyl cinnamate 
• 25347-44-8 racem.-3,4-diphenyl-adipic acid 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 1896-62-4 (E)-benzalacetone 
• 91-64-5 coumarin 
• 14371-10-9 (E)-3-phenylpropenal 

Downstream Products

• 7433-75-2 trans-1,2-diphenylcyclopentane 
• 7433-53-6 cis-1,2-diphenylcylopentane 
• 25347-44-8 3,4-diphenyl-adipic acid 
• 61883-07-6 meso-3,4-diphenyl-adipic acid dimethyl ester 
• 25347-44-8 racem.-3,4-diphenyl-adipic acid 
• 15898-52-9 (+/-)-3,4-diphenylhexane-1,6-diol 
• 13351-28-5 trans-3,4-diphenylcyclopentanone 

Relevant articles and documents

Hydroxylated HMPA enhances both reduction potential and proton donation in SmI2 reactions

HMPA is known to increase the reduction potential of SmI2. However, in many cases, the transferred electron returns from the radical anion of the substrate back to the Sm3+. This could be avoided by an efficient trapping of the radical anion: e.g., by protonation. However, bimolecular protonation by a proton donor from the bulk may be too slow to compete with the back electron transfer process. An efficient unimolecular protonation could be achieved by using a proton donor which complexes to SmI2, in which case the proton is unimolecularly transferred within the ion pair. A derivative of HMPA in which one of the methyl groups was substituted by a CH2CH2OH unit was synthesized. Cyclic voltammetry studies have shown that it resembles HMPA in its ability to enhance the reduction potential of SmI2, and reactivity studies show that it has also efficient proton shift capabilities. The various aspects of this additive were examined in the reactions of SmI2 with three substrates: benzyl chloride, methyl cinnamate, and anthracene.

Cathodic reductive coupling of methyl cinnamate on boron-doped diamond electrodes and synthesis of new neolignan-type products

The electroreduction reaction of methyl cinnamate on a boron-doped diamond (BDD) electrode was investigated. The hydrodimer, dimethyl 3,4-diphenylhexanedioate (racemate/meso = 74:26), was obtained in 85% yield as the major product, along with small amounts of cyclic methyl 5-oxo-2,3-diphenylcyclopentane-1-carboxylate. Two new neolignan-type products were synthesized from the hydrodimer.

Stereoselective hydrocoupling of cinnamic acid esters by electroreduction: Application to asymmetric synthesis of hydrodimers

The electroreduction of Ar-substituted methyl cinnamates in acetonitrile gave all-trans cyclized hydrodimers stereoselectively (58-90% de). In all cases, small amounts (2-symmetric dl-3,4-diaryladipic acids and trans-3,4-diarylcyclopentanones. The chiral auxiliary [(1R)-exo]-3-exo-(diphenylmethyl)borneol, prepared from (1R)-(+)-camphor, was highly effective for the stereoselective hydrocoupling of its cinnamates by electroreduction. From the resulting hydrodimers, (3R,4R)-3,4-diaryladipic acid esters and (3R,4R)-3,4-diarylhexane-1,6-diols were synthesized in 87-95% ee.