104621-38-7

Basic information

• Product Name: (E)-2-Benzoyl-1-<(3,4-dimethoxyphenyl)methylene>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• Synonyms: (E)-2-Benzoyl-1-<(3,4-dimethoxyphenyl)methylene>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• CAS NO: 104621-38-7
• Molecular Weight: 445.515
• Mol File: 104621-38-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (E)-2-Benzoyl-1-<(3,4-dimethoxyphenyl)methylene>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-2-Benzoyl-1-<(3,4-dimethoxyphenyl)methylene>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline(104621-38-7)
• EPA Substance Registry System: (E)-2-Benzoyl-1-<(3,4-dimethoxyphenyl)methylene>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline(104621-38-7)

Safety Data

• Hazardous Substances Data: 104621-38-7(Hazardous Substances Data)

Upstream product

• 135574-17-3 (1R,2S)-2-(2,2-Dimethoxy-ethylamino)-1,2-bis-(3,4-dimethoxy-phenyl)-ethanol 
• 135574-68-4 (4R,5R)-4,5-Bis-(3,4-dimethoxy-phenyl)-[1,3,2]dioxathiolane 2,2-dioxide 
• 135574-16-2 (4R,5R)-4,5-Bis-(3,4-dimethoxy-phenyl)-[1,3,2]dioxathiolane 2-oxide 
• 135574-15-1 (2R*,3R*)-2,3-bis(3,4-dimethoxyphenyl)oxirane 
• 98-88-4 benzoyl chloride 
• 6957-27-3 3,4-dihydropapaverine 
• 7732-18-5 water 
• 135574-18-4 Benzoic acid (R)-((S)-2-benzoyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-(3,4-dimethoxy-phenyl)-methyl ester 
• 110-86-1 pyridine 

Relevant articles and documents

General asymmetric synthesis of isoquinoline alkaloids. Enantioselective hydrogenation of enamides catalyzed by BINAP-ruthenium(II) complexes

In the presence of a small amount of RuX2[(R)- or (S)-BINAP] (X = anionic ligand) a wide range of (Z)-2-acyl-1-benzylidene-1,2,3,4- tetrahydroisoquinolines are hydrogenated to give the saturated products in nearly quantitative yields and in high (up to 100%) optical yields. The enamide substrates are selectively prepared by N-acylation of the corresponding 1-benzylated 3,4-dihydroisoquinolines under suitable acylation conditions; some crystalline materials having low solubility are obtained by a second-order Z/E stereomutation technique utilizing the double-bond photolability and lattice energy effects. This asymmetric hydrogenation sets the key stereogenic center in a predictable manner, either R or S flexibly, at the C(1) position of the benzylated tetrahydroisoquinolines. The chiral products are converted by standard functional group modification to tetrahydropapaverine, laudanosine, tretoquinol, norreticuline, etc. Hydrogenation of the simple 1-methylene substrate is used for synthesis of salsolidine. This enantioselective hydrogenation is applied to the synthesis of morphine and its artificial analogues such as morphinans and benzomorphans of either chirality. A mnemonic device is presented for predicting the reactivity and enantiofacial selection of the BINAP-Ru catalyzed hydrogenation. Reaction with BINAP-Rh catalyst proceeds with a lower enantioselectivity and an opposite sense of asymmetric induction.

Short-cut in the pomeranz-fritsch synthesis of 1-benzyl-isoquinolines; short and efficient syntheses of norrecticuline derivatives and of papaverine

A new methodology for the Pomeranz-Fritsch synthesis of 1-benzyl-1,2-dihydroisoquinolines avoiding pavine or isopavine troubles, has been developed. These intermediates could be reduced to their 1,2,3,4-tetrahydro congeners or aromatized to give isoquinolines, as it was demonstrated by the synthesis of some norrecticuline derivatives 4-7 and of papaverin 8.