116172-20-4

Basic information

• Product Name: 2(1H)-Isoquinolinecarboxaldehyde, 3,4,5,6,7,8-hexahydro-1-[(4-methoxyphenyl)methylene]-, (Z)-
• CAS NO: 116172-20-4
• Molecular Formula: C18H21NO2
• Molecular Weight: 283.37
• Mol File: 116172-20-4.mol

Chemical Properties

• CAS DataBase Reference: 2(1H)-Isoquinolinecarboxaldehyde, 3,4,5,6,7,8-hexahydro-1-[(4-methoxyphenyl)methylene]-, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(1H)-Isoquinolinecarboxaldehyde, 3,4,5,6,7,8-hexahydro-1-[(4-methoxyphenyl)methylene]-, (Z)-(116172-20-4)
• EPA Substance Registry System: 2(1H)-Isoquinolinecarboxaldehyde, 3,4,5,6,7,8-hexahydro-1-[(4-methoxyphenyl)methylene]-, (Z)-(116172-20-4)

Safety Data

• Hazardous Substances Data: 116172-20-4(Hazardous Substances Data)

Upstream product

• 3399-73-3 2-(1-cyclohexenyl)ethylamine 
• 51072-34-5 N-(2-cyclohex-1-enylethyl)-2-(4-methoxyphenyl)-acetamide 
• 104-01-8 4-Methoxyphenylacetic acid 
• 51072-35-6 1-(4-methoxybenzyl)-3,4,5,6,7,8-hexahydro-isoquinoline 
• 10535-67-8 trimethylacetic formic anhydride 

Downstream Products

• 125-71-3 dextromethorphan 
• 28973-48-0 (+)-3-methoxy-N-formylmorphinan 
• 29144-31-8 (S)-2-Formyl-1-<(4-methoxyphenyl)methyl>-1,2,3,4,5,6,7,8-octahydroispquinoline 
• 51773-23-0 (R)-2-Formyl-1-<(4-methoxyphenyl)methyl>-1,2,3,4,5,6,7,8-octahydroispquinoline 

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.

GENERAL ASYMMETRIC SYNTHESIS OF BENZOMORPHANS AND MORPHINANS VIA ENANTIOSELECTIVE HYDROGENATION

A variety of optically active benzomorphans including metazocine and pentazocine as well as dextromethorphan, a morphinan, are obtainable by using the BINAP-ruthenium(II) catalyzed enantioselective hydrogenation as key operation.