59224-99-6

Basic information

• Product Name: 2(1H)-Quinolinone, octahydro-, trans-
• CAS NO: 59224-99-6
• Molecular Formula: C9H15NO
• Molecular Weight: 153.224
• Mol File: 59224-99-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 151 °C
• Boiling Point: 321.4±11.0 °C(Predicted)
• Density: 1.014±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2(1H)-Quinolinone, octahydro-, trans-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(1H)-Quinolinone, octahydro-, trans-(59224-99-6)
• EPA Substance Registry System: 2(1H)-Quinolinone, octahydro-, trans-(59224-99-6)

Safety Data

• Hazardous Substances Data: 59224-99-6(Hazardous Substances Data)

Upstream product

• 10333-11-6 3,4,5,6,7,8-hexahydro-2-quinolinone 
• 553-03-7 3,4-dihydro-2(1H)-quinolone 
• 108-94-1 cyclohexanone 
• 59-31-4 2-hydroxyquinoline 
• 4594-78-9 cyclohexanone-2-propionitrile 
• 103621-58-5 trans-2-(methylamino)-3,4,5,6,7,8,9,9a-octahydroquinoline 

Downstream Products

• 87624-03-1 (4aS,8aS)-3-Chloro-octahydro-quinolin-2-one 
• 80828-13-3 rac-trans-octahydroindole-2-carboxylic acid 
• 80828-13-3 (2R,3aR,7aS)-Octahydro-indole-2-carboxylic acid 
• 10343-99-4 decahydroquinoline 
• 80828-13-3 (+/-)-(2R,3aS,7aS)-octahydroindole-2-carboxylic acid 
• 80828-13-3 (+/-)-(2S,3aS,7aS)-octahydroindole-2-carboxylic acid 
• 87624-03-1 (4aR,8aS)-3-Chloro-octahydro-quinolin-2-one 
• 90950-13-3 (+/-)-3-(trans-2-amino-cyclohexyl)-propionic acid 

Relevant articles and documents

Diastereoselective Rhodium-Catalyzed Hydrogenation of 2-Oxindoles and 3,4-Dihydroquinolones

The benzene ring of indolin-2-ones (2-oxindoles) and 3,4-dihydroquinol-2-ones was converted to a saturated cyclohexane ring by hydrogenation in the presence of the rhodium complex Cy(CAAC)Rh(cod)Cl. The stereoselectivity of the process was found to be high with respect to both external substituent R1 within the saturated part of the heterocyclic ring and substituent X on the benzene ring. Twenty-one hexahydroindolin-2(3H)-ones (70-99% yield, dr = 83/17 to >99/1) and twelve octahydro-2(1H)-quinolinones (87-96% yield, dr = 64/36 to >99/1) were obtained with the major diastereoisomer exhibiting the hydrogen atoms in an all-cis arrangement. The high tolerance toward functional groups and the compatibility with existing stereogenic centers are key features of the hydrogenation protocol presented here.

Catalytic Kinetic Resolution of Disubstituted Piperidines by Enantioselective Acylation: Synthetic Utility and Mechanistic Insights

The catalytic kinetic resolution of cyclic amines with achiral N-heterocyclic carbenes and chiral hydroxamic acids has emerged as a promising method to obtain enantio-enriched amines with high selectivity factors. In this report, we describe the catalytic kinetic resolution of disubstituted piperdines with practical selectivity factors (s, up to 52) in which we uncovered an unexpected and pronounced conformational effect resulting in disparate reactivity and selectivity between the cis- and trans-substituted piperidine isomers. Detailed experimental and computational studies of the kinetic resolution of various disubstituted piperidines revealed a strong preference for the acylation of conformers in which the α-substituent occupies the axial position. This work provides further experimental and computational support for the concerted 7-member transition state model for acyl transfer reagents and expands the scope and functional group tolerance of the secondary amine kinetic resolution.

Ruthenium-Catalyzed Hydration of Nitriles and Transformation of δ-Keto Nitriles to Ene-Lactams

Hydration of nitriles and transformation of δ-keto nitriles to ene-lactams can be performed efficiently by using RuH2(PPh3)4 catalyst under mild conditions.The effectiveness of the reaction is illustrated by the short-step synthesis of (-)-pumiliotoxin C.