116576-40-0

Basic information

• Product Name: AURORA 891
• Synonyms: AURORA 891
• CAS NO: 116576-40-0
• Molecular Formula: C₁₄H₁₆ClNO
• Molecular Weight: 249.74
• Mol File: 116576-40-0.mol

Chemical Properties

• Melting Point: 127-128 °C
• Boiling Point: 433.1±24.0 °C(Predicted)
• Appearance: /
• Density: 1.191±0.06 g/cm3(Predicted)
• PKA: -0.92±0.20(Predicted)
• CAS DataBase Reference: AURORA 891(CAS DataBase Reference)
• NIST Chemistry Reference: AURORA 891(116576-40-0)
• EPA Substance Registry System: AURORA 891(116576-40-0)

Safety Data

• Hazardous Substances Data: 116576-40-0(Hazardous Substances Data)

Upstream product

• 1796-25-4 1-(2-bromoacetyl)piperidine 
• 104-88-1 4-chlorobenzaldehyde 
• 72292-84-3 1,1-dimethoxy-1-(N-piperidinyl)ethane 
• 146060-34-6 fluoroiodomethyl piperidino ketone 
• 321-77-7 fluorochloromethyl piperidino ketone 
• 27982-53-2 (1-piperidinylcarbonylmethylene)triphenylphosphorane 
• 3157-65-1 N-(p-chlorobenzylidene)-p-toluenesulfonamide 

Relevant articles and documents

Stereoselective olefination of N-sulfonyl imines with stabilized phosphonium ylides for the synthesis of electron-deficient alkenes

An unprecedented protocol has been developed for thestereoselective synthesis of structurally diverse electron-deficient alkenes in moderate to excellent yields from readily accessible N-sulfonyl imines and stabilized phosphonium ylides. Significantly, the olefination reaction of N-sulfonylimines with nitrile-stabilized phosphonium ylides affords an array of α,β-unsaturated nitriles with high Z selectivity, and the reactions with ester-, amide-, and ketone-stabilized phosphonium ylides afford α,β-unsaturated esters, amides, and ketones with high E selectivity, respectively. Spectroscopic analysis of the reaction mixtures and trapping of the intermediates allow plausible mechanisms to be proposed. Initialimine/ylide addition leads to the formation of betaines that cyclize to form 1,2-azaphosphetanes that subsequently eliminate iminophosphoranes to yield alkenes. For the synthesis of electron-deficient 1,2-disubstituted alkenes, the presence of an electron-withdrawing group in the betaine allows rapid interconversion between its two diastereomers through proton transfer. The Z/E selectivity for alkene synthesis is determined by the different rates at which the two betaine diastereomers form the corresponding 1,2-azaphosphetane diastereomers. In contrast, the Z/E selectivity for the synthesis of electron-deficient trisubstituted alkenes originates from the diastereoselective addition of stabilized phosphonium ylides to N-sulfonyl imines.

Synthesis of 1-Fluoro-2-Phenylvinyl Piperidino Ketones

A new palladium-catalysed synthesis of 1-fluoro-2-phenylvinyl piperidino ketones is described.

A new one-pot synthesis of α,β-unsaturated amides

A new one-pot synthesis of α,β-unsaturated amides with high stereoselectivity by the reaction of aldehydes with bromoacetamides promoted by tri-n-butylphosphine and zinc is described.

Palladium-catalyzed conversion of aldehydes to (2E)-, (2E,4E)-unsaturated amides in the presence of tri-n-butyl-arsine or phosphine

Palladium-catalyzed conversion of aldehydes to (2E)-, (2E,4E)-unsaturated amides in the presence of tri-n-butyl-arsine or -phosphine is described.

Lactam and Amide Acetals: Part XVII - Reactions of 1,1-Dimethoxy-1-(N-piperidinyl)ethane and 2-Ethoxy-1-methylindole with Electrophiles

Reactions of araldehydes with 1,1-dimethoxy-1-(N-piperidinyl)ethane (1) yield 3-aryl-1-(N-piperidinyl)-2-propen-1-ones (3-10), while 2-ethoxy-1-methylindole (2) reacts with araldehydes to afford aryldi-(2-ethoxy-1-methylindole-3-yl)methanes (11-16).Reaction of 2 with phenyl isocyanate and phenyl isothiocyanate gives 2-ethoxy-1-methyl-3-phenylcarbamoyl and thiocarbamoylindoles (17 and 18) respectively.