4593-16-2

Basic information

• Product Name: 1-ACETYL-3-METHYLPIPERIDINE
• Synonyms: 1-ACETYL-3-METHYLPIPERIDINE;1-acetyl-3-methyl-piperidin;1-(3-methyl-1-piperidyl)ethanone;1-(3-methylpiperidin-1-yl)ethanone;1-(3-Methyl-1-piperidinyl)-ethanone;1-Acetyl-3-pipecoline
• CAS NO: 4593-16-2
• Molecular Formula: C₈H₁₅NO
• Molecular Weight: 141.21
• EINECS: 224-983-2
• Product Categories: API intermediates;Building Blocks;Heterocyclic Building Blocks;Piperidines;Building Blocks;C8;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 4593-16-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: −15 °C(lit.)
• Boiling Point: 239 °C(lit.)
• Flash Point: 224 °F
• Appearance: /
• Density: 0.974 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0406mmHg at 25°C
• Refractive Index: n20/D 1.476(lit.)
• CAS DataBase Reference: 1-ACETYL-3-METHYLPIPERIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ACETYL-3-METHYLPIPERIDINE(4593-16-2)
• EPA Substance Registry System: 1-ACETYL-3-METHYLPIPERIDINE(4593-16-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 4593-16-2(Hazardous Substances Data)

Usage

Description

1-Acetyl-3-methylpiperidine is an organic compound with the molecular formula C8H15NO. It is a derivative of piperidine, a heterocyclic amine, and features an acetyl group at the 1st position and a methyl group at the 3rd position. 1-ACETYL-3-METHYLPIPERIDINE is known for its potential applications in various chemical and pharmaceutical processes due to its unique structural properties.

Uses

1. Used in Chemical Synthesis:
1-Acetyl-3-methylpiperidine is used as a reactant for regioselective amidyl radical cyclization and regioselective oxidation of cyclic amino compounds. These reactions are crucial in the synthesis of complex organic molecules and pharmaceutical compounds, where the selective formation of specific products is essential.
2. Used in Pharmaceutical Research:
1-Acetyl-3-methylpiperidine is used as a piperidine ligand to investigate the enzymatic activity and three-dimensional structure of non-peptide ligand-cyclophilin complexes. Cyclophilin is a protein that plays a role in various cellular processes, and understanding its interactions with different ligands can provide insights into the development of new drugs targeting these proteins.

InChI:InChI=1/C8H15NO/c1-7-4-3-5-9(6-7)8(2)10/h7H,3-6H2,1-2H3

Upstream product

• 1039553-34-8 C₁₄H₁₉NOS 
• 108-24-7 acetic anhydride 
• 626-56-2 3-Methylpiperidine 
• 75-36-5 acetyl chloride 

Downstream Products

• 1568025-98-8 1-(3-methylpiperidin-1-yl)-3-phenylpropane-1,3-dione 
• 2162-86-9 1-ethyl-3-methyl-piperidine 

Relevant articles and documents

Development of highly regioselective amidyl radical cyclization based on lone pair-lone pair repulsion

(Chemical Equation Presented) The substituent effect on the reactivity and regioselectivity of N-(4-pentenyl)amidyl radical cyclization was investigated. Exclusive 6-endo cyclization was observed for N-(4-pentenyl)amidyl radicals with internal vinylic heteroatom substitution (Cl, Br, I, OMe, SEt). The substituent on the carbonyl group also showed a significant influence on the reactivity of amidyl radicals, which increases in the order of Ph a result, the photostimulated reactions of N-(4-halopent-4-enyl)amides and carbamates (X = Cl, Br, I) with DIB/I2 or Pb(OAc)4/I 2 led to the efficient and exclusive formation of the corresponding piperidines while those of N-(5-halopent-4-enyl)amides afforded the pyrrolidine products only. The halogen-substitution effect also allowed the 6-exo and 7-endo amidyl radical cyclization to proceed in a highly regioselective manner. The above experimental results, in combination with theoretical analyses, revealed that the lone pair-lone pair repulsion between the nitrogen radical and the vinylic heteroatom played an important role in controlling the regioselectivity of cyclization.

NMR Spectra and Stereochemistry of N-Acetyl and N-Benzoyl Derivatives of Solasodine

N-Acetylation of solasodine gives only one rotameric N-acetyl derivative compared with N-acetyl-3-methylpiperidine, which exists in solution as two equally populated rotamers.The 1H and 13C NMR spectra (CDCl3) of O,N-diacetyl- and O-acetyl-N-benzoylsolasodine indicate significant deviations from F-ring chair geometry.Opening of the F ring of these derivatives in CDCl3 solution at 25 deg C, to give the corresponding furosta-5,20(22)-diene derivatives, was ascertained by NMR spectroscopy.Key Words: Solasodine O,N-Diacetylsolasodine O-Acetyl-N-benzoylsolasodine 3β-Acetoxy-26-acetamidofurosta-5,20(22)-diene 3β-Acetoxy-26-benzamidofurosta-5,20(22)-diene