23581-42-2

Basic information

• Product Name: 2H-Quinolizin-2-one, octahydro-
• Synonyms: 2H-Quinolizin-2-one, octahydro-;1,3,4,6,7,8,9,9a-octahydroquinolizin-2-one
• CAS NO: 23581-42-2
• Molecular Formula: C₉H₁₅NO
• Molecular Weight: 153.2215
• Mol File: 23581-42-2.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 142-144 °C(Press: 16 Torr)
• Appearance: /
• Density: 1.06±0.1 g/cm3(Predicted)
• PKA: 8.18±0.20(Predicted)
• CAS DataBase Reference: 2H-Quinolizin-2-one, octahydro-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Quinolizin-2-one, octahydro-(23581-42-2)
• EPA Substance Registry System: 2H-Quinolizin-2-one, octahydro-(23581-42-2)

Safety Data

• Hazardous Substances Data: 23581-42-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 3457, 1956 DOI: 10.1021/ja01595a053

Upstream product

• 1258431-03-6 2-oxo-octahydro-quinolizine-3-carboxylic acid ethyl ester 
• 109-06-8 α-picoline 
• 1312456-09-9 C₉H₁₅NO 
• 27132-81-6 2,4-dimethyl-penta-1,4-dien-3-one 
• 49552-70-7 4-(1,3-dioxolan-2-yl)butan-1-amine 
• 34418-91-2 2,3,4,5-tetrahydropyridine N-oxide 
• 21938-23-8 5-Aminopentanal Diethyl Acetal 
• 337974-51-3 8-[(tert-butoxycarbonyl)amino]-1-[(4'-methylphenyl)sulfonyl]-1-nonen-3-one 
• 2739-98-2 ethyl 2-(pyridinyl-2)acetate 
• 2739-99-3 2-ethoxycarbonylmethylpiperidine 
• 24103-75-1 4-methoxy-2-methylpyridine 
• 87265-40-5 4-(5,5-Diethoxy-pentylamino)-butan-2-one 
• 106051-13-2 hexahydrospiroisoxazolo<2,3-a>pyridine> 
• 99392-94-6 1-(2-ethoxycarbonyl)ethyl-2-ethoxycarbonylmethylpiperidine 

Downstream Products

• 475301-86-1 3-methyldecahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocine 
• 475301-86-1 (1S,5R,11aR)-3-methyldecahydro-1H-1,5-methanopyrido[1,2-a]-[1,5]diazocine 
• 475301-86-1 (+)-sparteine surrogate 
• 99392-98-0 1,2,3,4,6,7,8,9-octahydro-2-<β-(3,4-dimethoxyphenethylamino)ethyl>-9aH-quinolizine 
• 99405-57-9 2-(3,4-dimethoxyphenethylcarbamoylmethyl)-1,2,3,4,6,7,8,9-octahydro-9aH-quinolizine 
• 98482-42-9 4-Acetylamino-5-chloro-2-methoxy-N-(2R,9aR)-octahydro-quinolizin-2-yl-benzamide 
• 98482-44-1 4-Acetylamino-5-chloro-2-methoxy-N-(2R,9aS)-octahydro-quinolizin-2-yl-benzamide 
• 98482-28-1 (2β,9aα)-4-amino-5-chloro-2-methoxy-N-(octahydro-2H-quinolizin-2-yl)benzamide 
• 98482-30-5 (2α,9aα)-4-amino-5-chloro-2-methoxy-N-(octahydro-2H-quinolizin-2-yl)benzamide 
• 67092-45-9 2-amino-quinolizidine 
• 4968-90-5 eq-quinolizidin-2-ylmethanol 
• 475301-86-1 (+)-sparteine surrogate 
• 475301-86-1 (-)-sparteine 
• 475301-86-1 11-methyl-7,11-diazatricyclo<7.3.1.0^2.7>tridecane 

Relevant articles and documents

Revisiting the sparteine surrogate: Development of a resolution route to the (-)-sparteine surrogate

The improved performance of the sparteine surrogate compared to sparteine in a range of applications has highlighted the need to develop an approach to the (-)-sparteine surrogate, previously inaccessible in gram-quantities. A multi-gram scale, chromatography-free synthesis of the racemic sparteine surrogate and its resolution via diastereomeric salt formation with (-)-O,O′-di-p-toluoyl-l-tartaric acid is reported. Resolution on a 10.0 mmol scale gave the diastereomeric salts in 33% yield from which (-)-sparteine surrogate of 937 er was generated. This work solves a key limitation: either enantiomer of the sparteine surrogate can now be readily accessed.

A two-step, formal [4 + 2] approach toward piperidin-4-ones via au catalysis

(Chemical Equation Presented) An efficient, formal [4 + 2] synthesis of synthetically valuable piperidin-4-ones from secondary amines in two steps has been achieved via a key gold catalysis without the purification of tertiary amine intermediates. This reaction is selective toward the less-substituted alkyl group and shows moderate to excellent diastereoselectivities. Its synthetic potential in alkaloid synthesis is demonstratedin a highly diastereoselective synthesis of (±)-cermizine C.

5-HT1F agonists

The present invention relates to a compound of formula (I): or a pharmaceutical acid addition salt thereof; which is useful for activating 5-HT1freceptors and inhibiting protein extravasation in a mammal.