17366-51-7

Basic information

• Product Name: (Z)-2-Acetyl-1-<(3,4-dimethoxyphenyl)methylene>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• Synonyms: (Z)-2-Acetyl-1-<(3,4-dimethoxyphenyl)methylene>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• CAS NO: 17366-51-7
• Molecular Weight: 383.444
• Mol File: 17366-51-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (Z)-2-Acetyl-1-<(3,4-dimethoxyphenyl)methylene>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-2-Acetyl-1-<(3,4-dimethoxyphenyl)methylene>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline(17366-51-7)
• EPA Substance Registry System: (Z)-2-Acetyl-1-<(3,4-dimethoxyphenyl)methylene>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline(17366-51-7)

Safety Data

• Hazardous Substances Data: 17366-51-7(Hazardous Substances Data)

Upstream product

• 6957-27-3 3,4-dihydropapaverine 
• 108-24-7 acetic anhydride 
• 5884-22-0 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3.4-dihydroisoquinoline hydrochloride 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 10313-60-7 3,4-dimethoxyphenylacetyl chloride 
• 139-76-4 N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide 
• 75-36-5 acetyl chloride 

Downstream Products

• 4747-98-2 S-(-)-Norlaudanosine 
• 339067-73-1 N-(2-{2-[(2-bromo-4,5-dimethoxy-phenyl)-acetyl]-4,5-dimethoxy-phenyl}-ethyl)-acetamide 
• 339067-74-2 N-(2-{2-[2-(2-bromo-4,5-dimethoxyphenyl)-1-methoxyethyl]-4,5-dimethoxyphenyl}ethyl)acetamide 
• 2129-61-5 2-(2-acetamidoethyl)-4,4',5,5'-tetramethoxydeoxybenzoin 
• 860-24-2 (R)-2-Acetyl-1-<(3,4-dimethoxyphenyl)methyl>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 860-23-1 (S)-2-Acetyl-1-<(3,4-dimethoxyphenyl)methyl>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 85433-42-7 N-trifluoroacetyl-1-(3,4-dimethoxybenzyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline 
• 522-57-6 papaveraldine 
• 20345-69-1 3,4-dihydropapaveraldine 

Relevant articles and documents

Total syntheses of 1-methyl-1,2,3,4-tetrahydronaphtho[2,1-f]isoquinolines involving free radical cyclizations induced by tributyltin(IV) hydride

We describe two total syntheses of 1-methyl-1,2,3,4-tetrahydronaphtho[1,2-f]isoquinolines based on free radical cyclization. One of them includes the cyclization of N-{2-[2-(2-bromophenyl)-1-methoxyethyl]phenylethyl}acetamides and subsequent transformation of the resulting N-[2-(10-methoxy-9,10-dihydro-1-phenanthryl)ethyl]acetamides. The second is based on the known cyclization of 1-(2-bromobenzyl)isochroman-3-ones to 4,5,6a,7-tetrahydrodibenzo[de,g]chroman-3-ones followed by transformation of the resulting 2-(1-phenanthryl)acetamides.

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.

Asymmetric Synthesis of Isoquinoline Alkaloids by Homogeneous Catalysis

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