436145-75-4

Basic information

• Product Name: (4R,9aS)-4-(3,4-dimethoxyphenyl)octahydro-2H-quinolizin-2-one
• Synonyms: (4R,9aS)-4-(3,4-dimethoxyphenyl)octahydro-2H-quinolizin-2-one
• CAS NO: 436145-75-4
• Molecular Weight: 289.375
• Mol File: 436145-75-4.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (4R,9aS)-4-(3,4-dimethoxyphenyl)octahydro-2H-quinolizin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,9aS)-4-(3,4-dimethoxyphenyl)octahydro-2H-quinolizin-2-one(436145-75-4)
• EPA Substance Registry System: (4R,9aS)-4-(3,4-dimethoxyphenyl)octahydro-2H-quinolizin-2-one(436145-75-4)

Safety Data

• Hazardous Substances Data: 436145-75-4(Hazardous Substances Data)

Upstream product

• 689257-75-8 (E)-N-methoxy-N-methyl-3-(3,4-dimethoxyphenyl)-acrylamide 
• 39856-08-1 3,4-dimethoxy-cinnamoyl chloride 
• 2316-26-9 3,4-dimethoxycinnamic acid 
• 505-18-0 2,3,4,5-tetrahydropyridine 
• 110-89-4 piperidine 
• 2858-67-5 1-[(2S)-piperidin-2-yl]acetone 
• 2156-71-0 N-chloropiperidine 
• 1214914-34-7 (S)-2-(2-oxo-propyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 522-33-8 Tripiperidin 
• 15001-27-1 O-methyldehydrozingerone 
• 86953-81-3 tert-butyl 2-hydroxypiperidine-1-carboxylate 
• 1402830-66-3 (+)-(E)-tert-butyl 2-(4-(3,4-dimethoxyphenyl)-2-oxobut-3-enyl)piperidine-1-carboxylate 
• 436145-72-1 (10S)-4-(3,4-dimethoxyphenyl)-3-(p-toluenesulfonyl)-1,6,7,8,9,9a-hexahydroquinolizin-2-one 
• 436861-56-2 (S)-4-(3,4-Dimethoxy-phenyl)-3-(toluene-4-sulfonyl)-octahydro-quinolizin-2-ol 

Relevant articles and documents

Double asymmetric intramolecular aza-Michael reaction: a convenient strategy for the synthesis of quinolizidine alkaloids

A new methodology to access the quinolizidine skeleton in an asymmetric fashion was devised. It involves two consecutive intramolecular aza-Michael reactions of sulfinyl amines bearing a bis-enone moiety, in turn generated by a monodirectional cross metat

Biomimetic Organocatalytic Approach to 4-Arylquinolizidine Alkaloids and Application in the Synthesis of (-)-Lasubine II and (+)-Subcosine II

An enantioselective, biomimetic organocatalytic synthesis of 4-arylquinolizidin-2-ones, key intermediates in the synthesis of several Lythraceae alkaloids, was developed. The methodology features S-proline-mediated Mannich/aza-Michael reactions of readily available arylideneacetones and Δ1-piperideine. The total syntheses of (-)-lasubine II and (+)-subcosine II as well as the formal syntheses of structurally related Lythraceae alkaloids were achieved. The use of Δ1-pyrroline in the Mannich/aza-Michael reaction provides enantiomerically enriched 5-arylindolizidin-7-ones, which are precursors to nonopiate antinociceptive agents.

Copper(I)-catalyzed enantioselective incorporation of ketones to cyclic hemiaminals for the synthesis of versatile alkaloid precursors

A general catalytic enantioselective method that can produce five-, six-, and seven-membered N-heterocycles possessing various ketone moieties starting from stable and easily available cyclic hemiaminals and ketones was developed. The method involves three successive steps in one pot (aldol addition, dehydration, and enantioselective intramolecular aza-Michael reaction), all of which are promoted by a chiral copper(I)-conjugated Bronsted base catalyst. This method is useful for rapid access to versatile chiral building blocks for the synthesis of drug-lead alkaloids.