116172-18-0

Basic information

• Product Name: 1(2H)-Pyridinecarboxaldehyde, 5,6-dihydro-2-[(4-methoxyphenyl)methyl]-3,4-dimethyl-, (S)-
• CAS NO: 116172-18-0
• Molecular Formula: C16H21NO2
• Molecular Weight: 259.348
• Mol File: 116172-18-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1(2H)-Pyridinecarboxaldehyde, 5,6-dihydro-2-[(4-methoxyphenyl)methyl]-3,4-dimethyl-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1(2H)-Pyridinecarboxaldehyde, 5,6-dihydro-2-[(4-methoxyphenyl)methyl]-3,4-dimethyl-, (S)-(116172-18-0)
• EPA Substance Registry System: 1(2H)-Pyridinecarboxaldehyde, 5,6-dihydro-2-[(4-methoxyphenyl)methyl]-3,4-dimethyl-, (S)-(116172-18-0)

Safety Data

• Hazardous Substances Data: 116172-18-0(Hazardous Substances Data)

Upstream product

• 60355-99-9 2-<(4-Methoxyphenyl)methylene>-3,4-dimethyl-5,6-dihydropyridine hydrochloride 
• 60355-98-8 N-(3'-methyl-3'-pentenyl)-4-methoxyphenylacetamide 
• 116172-15-7 (E)-3-methyl-3-pentenylamine 
• 116172-14-6 (E)-3-methyl-3-pentenenitrile 
• 497-02-9 (E)-2-methyl-2-buten-1-ol 
• 80-59-1 Tiglic acid 
• 99113-01-6 (S)-2-(4-methoxybenzyl)-3,4-dimethyl-1,2,5,6-tetrahydropyridine 
• 109-94-4 formic acid ethyl ester 
• 116172-10-2 (Z)-1-Formyl-2-<(4-methoxyphenyl)methylene>-3,4-dimethyl-1,2,5,6-tetrahydropyridine 

Downstream Products

• 70386-87-7 (S)-N-methyl-2-(4-methoxybenzyl)-3,4-dimethyl-1,2,5,6-tetrahydropyridine 
• 67009-58-9 (+)-metazocine 

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.

Asymmetric synthesis of 2-alkylpyrrolidines and piperidines. Synthesis of (+)-metazocine

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