221664-11-5

Basic information

• Product Name: (4S,9aS)-4-(3,4-dimethoxyphenyl)hexahydro-1H-quinolizin-2(6H)-one
• Synonyms: (4S,9aS)-4-(3,4-dimethoxyphenyl)hexahydro-1H-quinolizin-2(6H)-one
• CAS NO: 221664-11-5
• Molecular Weight: 289.375
• Mol File: 221664-11-5.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: (4S,9aS)-4-(3,4-dimethoxyphenyl)hexahydro-1H-quinolizin-2(6H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,9aS)-4-(3,4-dimethoxyphenyl)hexahydro-1H-quinolizin-2(6H)-one(221664-11-5)
• EPA Substance Registry System: (4S,9aS)-4-(3,4-dimethoxyphenyl)hexahydro-1H-quinolizin-2(6H)-one(221664-11-5)

Safety Data

• Hazardous Substances Data: 221664-11-5(Hazardous Substances Data)

Upstream product

• 505-18-0 2,3,4,5-tetrahydropyridine 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 69622-67-9 benzyl 2-hydroxypiperidine-1-carboxylate 
• 87905-98-4 5-<(benzyloxycarbonyl)amino>pentanol 
• 2858-66-4 (-)-pelletierine 
• 2858-67-5 1-[(2S)-piperidin-2-yl]acetone 
• 1214914-34-7 (S)-2-(2-oxo-propyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 1202039-12-0 (+)-(2R)-(2-oxopropyl)piperidine-1-carbamic acid tert-butylester 
• 2508-29-4 5-hydroxypentylamine 
• 184535-06-6 (+)-(2R)-(2-oxopropyl)piperidine-1-carbamic acid benzyl ester 
• 184535-17-9 (-)-(2S)-(2-oxopropyl)piperidine-1-carbamic acid benzyl ester 
• 1235511-86-0 C₁₄H₁₉NO₄ 

Downstream Products

• 68681-73-2 (-)-(2S,4S,9aS)-2-hydroxy-4-(3,4-dimethoxyphenyl)-decahydroquinolizidine 
• 386285-44-5 (2R,4S,9aS)-2-hydroxy-4-(3,4-dimethoxyphenyl)-decahydroquinolizidine 
• 77092-63-8 2-(p-hydroxyphenylpropionoyloxy)(a)-4-(3',4'-dimethoxyphenyl)(e)-trans-quinolizidine 
• 71480-97-2 2-(p-methoxyphenylpropionoyloxy)(a)-4-(3',4'-dimethoxyphenyl)(e)-trans-quinolizidine 
• 77092-60-5 2-(p-benzyloxyphenylpropionoyloxy)(a)-4-(3',4'-dimethoxyphenyl)(e)-trans-quinolizidine 
• 10183-64-9 Decinin 

Relevant articles and documents

Enantiodivergent Approach to the Synthesis of Cis-2,6-Disubstituted Piperidin-4-ones

Enantiopure β-amino ketone derivatives were synthesized by decarboxylative Mannich reaction of chiral N-tert-butanesulfinyl imines with β-keto acids and were subsequently transformed into cis-2,6-disubstituted piperidin-4-ones through an organocatalyzed condensation with aldehydes. Both enantiomers were accessible from the same precursors by inverting the order in the reaction sequence of the aldehydes involved in the imine formation and the intramolecular Mannich condensation. The synthesis of the piperidine alkaloids (+)-241D, (-)-epimyrtine, and (-)-lasubine II demonstrated the utility of this methodology.

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.