3-Methylenepiperidin-2-one

Base Information

• Chemical Name: 3-Methylenepiperidin-2-one
• CAS No.: 68074-14-6
• Molecular Formula: C6H9NO
• Molecular Weight: 111.144
• DSSTox Substance ID: DTXSID50457843
• Nikkaji Number: J1.792.481H
• Wikidata: Q82280872
• Mol file: 68074-14-6.mol

Synonyms:3-Methylenepiperidin-2-one;68074-14-6;3-methylidene-2-piperidinone;3-methylene-2-piperidone;3-METHYLENE-2-PIPERIDINONE;3-methylidenepiperidin-2-one;SCHEMBL2989968;DTXSID50457843;XFXHSJFUZPNEME-UHFFFAOYSA-N;MFCD13176083;AKOS006346831;SB43076;BS-17335;CS-0312427;D80229

Chemical Property of 3-Methylenepiperidin-2-one

Chemical Property:

• Melting Point: 55-57 °C
• Boiling Point: 110 °C(Press: 1 Torr)
• PSA: 32.59000
• Density: 1.01±0.1 g/cm3(Predicted)
• LogP: 0.72850
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 111.068413911
• Heavy Atom Count: 8
• Complexity: 129

Purity/Quality:

99% ^*data from raw suppliers

3-Methylenepiperidin-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=C1CCCNC1=O

Technology Process of 3-Methylenepiperidin-2-one

There total 13 articles about 3-Methylenepiperidin-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

3-(hydroxymethyl)-2-piperidinone (25219-43-6) → 3-methylidene-2-oxo-piperidine (68074-14-6)

Guidance literature:

With copper(l) iodide; dicyclohexyl-carbodiimide; In toluene; at 110 ℃; for 1.16667h;

DOI:10.1016/j.bmc.2014.07.004

Reference yield: 74.0%

carbon monoxide (201230-82-2) + HC2C3H6NHCH(CH3)C6H5 (930608-65-4) → 3-methylidene-2-oxo-piperidine (68074-14-6)

Guidance literature:

carbon monoxide; HC₂C₃H₆NHCH(CH₃)C₆H₅; With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; at 90 ℃; for 4h; Autoclave;

With methanol; chloro-trimethyl-silane; at 20 ℃; for 0.166667h;

DOI:10.1039/c1ob05145h

Reference yield: 67.0%

3-(hydroxymethyl)-2-pyrrolidinone (76220-94-5) → 3-methylidene-2-oxo-piperidine (68074-14-6)

Guidance literature:

With copper(l) iodide; dicyclohexyl-carbodiimide; In toluene; for 0.166667h; Heating;

DOI:10.1021/jm00133a021

upstream raw materials:

carbon monoxide

1-amino-pent-4-yne

3-(hydroxymethyl)-2-pyrrolidinone

3-(hydroxymethyl)-2-piperidinone

Downstream raw materials:

2-acetylthiomethyl-5-(p-methoxybenzyloxycarbonyl)aminopentanoic acid

2-Methylene-5-(p-methoxybenzyloxycarbonyl)aminopentanoic acid

3-methylene-2-oxo-piperidine-1-carboxylic acid benzyl ester

(6S,7S)-9-(tert-Butyl-dimethyl-silanyloxy)-8-methyl-1-oxo-7-prop-1-ynyl-2-aza-spiro[5.5]undec-8-ene-2-carboxylic acid benzyl ester

Refernces

• 1、 -. "COMPOSITIONS AND METHODS FOR SELECTIVELY DEPLETING SENESCENT CELLS". Paragraph 0417. . Retrieved 2016/02/26.
• 2、 Zachariassen, Zack G.,Thiele, Stefanie,Berg, Erik A.,Rasmussen, Pernille,Fossen, Torgils,Rosenkilde, Mette M.,V?ben?, Jon,Haug, Bengt Erik. "Design, synthesis, and biological evaluation of scaffold-based tripeptidomimetic antagonists for CXC chemokine receptor 4 (CXCR4)". . p. 4759 - 4769. Retrieved 2014/10/15.