19615-27-1

Basic information

• Product Name: 1-Acetyl-1,2,3,4-tetrahydropyridine
• Synonyms: 1-Acetyl-1,2,3,4-tetrahydropyridine
• CAS NO: 19615-27-1
• Molecular Formula: C₇H₁₁NO
• Molecular Weight: 125.1683
• Mol File: 19615-27-1.mol

Chemical Properties

• Boiling Point: 244.3°Cat760mmHg
• Flash Point: 109.5°C
• Appearance: /
• Density: 1.025g/cm³
• Vapor Pressure: 0.0305mmHg at 25°C
• Refractive Index: 1.492
• CAS DataBase Reference: 1-Acetyl-1,2,3,4-tetrahydropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Acetyl-1,2,3,4-tetrahydropyridine(19615-27-1)
• EPA Substance Registry System: 1-Acetyl-1,2,3,4-tetrahydropyridine(19615-27-1)

Safety Data

• Hazardous Substances Data: 19615-27-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H11NO/c1-7(9)8-5-3-2-4-6-8/h3,5H,2,4,6H2,1H3

Upstream product

• 522-33-8 Tripiperidin 
• 108-24-7 acetic anhydride 
• 522-33-8 α-tripiperideine 
• 618-42-8 1-piperidin-1-yl-ethanone 
• 18513-75-2 1-(1,2,3,6-tetrahydropyridin-1-yl)ethan-1-one 
• 63050-18-0 1-acetyl-2-methoxy-piperidine 
• 694-05-3 1,2,3,6-tetrahydropyridine 
• 110-89-4 piperidine 
• 67-56-1 methanol 

Downstream Products

• 18762-49-7 7-acetyl-3-phenyl-(3ar,7ac)-3a,4,5,6,7,7a-hexahydro-isoxazolo[5,4-b]pyridine 
• 83487-13-2 N-acetyl-1,4,5,6-tetrahydronicotinaldehyde 
• 18718-78-0 3-(3-phenyl-isoxazol-4-yl)-propylamine 
• 53508-16-0 (+)-maackiamine 

Relevant articles and documents

β-Functionalization of Saturated Aza-Heterocycles Enabled by Organic Photoredox Catalysis

The direct β-functionalization of saturated aza-heterocycles has remained a synthetic challenge because of the remote and unactivated nature of β-C-H bonds in these motifs. Herein, we demonstrate the β-functionalization of saturated aza-heterocycles enabl

The Effect of Ring-Size on the Anodic Oxidation of 'Cyclic Amides' in Methanol

The anodic oxidation of three 'cyclic amides' of type N-acylazacycloalkanes [5- (I), 6- (II) and 7-membered (III) rings] has been studied in methanol under constant current electrolysis, at C anodes and in the presence of various supporting electrolytes, and different concentrations of substrates. Four major products were formed in good yields by all three substrates, namely N-acyl, α-azacycloalkenes, N-acyl, α-methoxyazacycloalkanes, N-acyl, α-methoxy, α'-azacycloalkenes and N-acyl, α,α′-dimethoxyazacycloalkanes. The relative ratios among products and selectivity were found to be highly dependent on the nature of the electrolyte used, and to a lesser extent on substrate concentration. In terms of ring-size effect it was found that the rate of oxidation and current efficiency (yield) was in the order: I > II > III. Also the latter two behaved similarly (but different from I) when various supporting electrolytes were used.

Enantioselective, palladium-catalyzed α-arylation of N-Boc pyrrolidine: In situ react IR spectroscopic monitoring, scope, and synthetic applications

A comprehensive study of the enantioselective Pd-catalyzed α-arylation of N-Boc pyrrolidine has been carried out. The protocol involves deprotonation of N-Boc pyrrolidine using s-BuLi/(-)-sparteine in TBME or Et2O at -78 °C, transmetalation with ZnCl2 and Negishi coupling using Pd(OAc)2, t-Bu3P-HBF4 and the aryl bromide. This paper reports several new features including in situ React IR spectroscopic monitoring of the process; use of (-)-sparteine and the (+)-sparteine surrogate to access products with opposite configuration; development of a catalytic asymmetric lithiation-Negishi coupling reaction; extension to a wide range of heteroaromatic bromides; total synthesis of (R)-crispine A, (S)-nicotine and (S)-SIB-1508Y via short synthetic routes; and examples of α-vinylation of N-Boc pyrrolidine using vinyl bromides exemplified by the total synthesis of naturally occurring (+)-maackiamine (thus establishing its configuration as (R)). In this way, the full scope and limitations of the methodology are delineated.

Electroorganic Chemistry. 60. Electroorganic Synthesis of Enamides and Enecarbamates and Their Utilization in Organic Synthesis.

A variety of enecarbamates and enamides were synthesized from α-methoxy carbamates and α-methoxy amides prepared by anodic methoxylation of amine derivatives.Some new carbon-carbon bond-forming reactions and hydroxylation at the β position of amines have been accomplished by using these enecarbamates and enamides as key intermediates.Also, new synthetic routes of nicotinaldehyde and pyrrole derivatives have been exploited by utilizing anodic dimethoxylation of carbamates of piperidine and pyrrolidine, respectively.

Process for the preparation of cyclic enamides

Special cyclic enamides are prepared by splitting off alcohols catalytically from the corresponding alkoxylated cyclic amides, in the presence of at least one tetraalkylammonium and/or alkali metal salt of tetrafluoroboric acid and/or of hexafluorophosphoric acid as the catalyst, at a temperature of from about 120° to 250° C., distilling off the detached alcohol and isolating the formed enamide in known manner. Particularly preferred starting compounds are those cyclic amides which have been obtained by anodic alkoxylation of corresponding cyclic N-compounds in an alcohol in the presence of supporting electrolytes which are identical with the catalysts subsequently used for splitting off the alcohol, and by distilling off the alcohol from the reaction batch. The enamides are valuable starting products and intermediates for various syntheses, for example, syntheses of prostaglandins and of other pharmaceuticals.

Isomerization of N-Allylamides and -imides to Aliphatic Enamides by Iron, Rhodium, and Ruthenium Complexes

Substituted aliphatic N-propenylamides and -imides are readily sythesized from N-allylamides by double bond migration induced by rhodium or ruthenium hydrides.N-Propenylimides can be prepared from allylimides only in the presence of iron pentacarbonyl.