5,6-Dihydropyridin-2(1H)-one

Base Information

• Chemical Name: 5,6-Dihydropyridin-2(1H)-one
• CAS No.: 6052-73-9
• Molecular Formula: C5H7NO
• Molecular Weight: 97.1167
• Hs Code.: 2933399090
• European Community (EC) Number: 821-708-3
• UNII: 77GJ5LL56Z
• DSSTox Substance ID: DTXSID70209265
• Nikkaji Number: J603.318K
• Wikidata: Q27266584
• Metabolomics Workbench ID: 128405
• ChEMBL ID: CHEMBL2347636
• Mol file: 6052-73-9.mol

Synonyms:5,6-Dihydropyridin-2(1H)-one;6052-73-9;5,6-DIHYDRO-1H-PYRIDIN-2-ONE;2,3-dihydro-1H-pyridin-6-one;5,6-Dihydro-2(1H)-pyridinone;5,6-Dihydro-2(1H)-pyridone;2(1H)-Pyridone, 5,6-dihydro-;2(1H)-Pyridinone, 5,6-dihydro-;UNII-77GJ5LL56Z;77GJ5LL56Z;1,2,5,6-tetrahydropyridin-2-one;MFCD19216835;CHEMBL2347636;AMY9701;DTXSID70209265;OXRRHYRRQWIHIV-UHFFFAOYSA-N;AKOS006350898;CS-W006454;AC-30520;AS-59359;SY259179;FT-0666873;EN300-211355;A848891;Q27266584

Chemical Property of 5,6-Dihydropyridin-2(1H)-one

Chemical Property:

• Vapor Pressure: 0.00256mmHg at 25°C
• Melting Point: 187-188℃
• Refractive Index: 1.478
• Boiling Point: 287 °C at 760 mmHg
• PKA: 15.07±0.20(Predicted)
• Flash Point: 158 °C
• PSA: 29.10000
• Density: 1.052 g/cm³
• LogP: 0.39130
• Storage Temp.: 2-8°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 97.052763847
• Heavy Atom Count: 7
• Complexity: 107

Purity/Quality:

98%,99%, ^*data from raw suppliers

5,6-Dihydro-2(1H)-pyridinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNC(=O)C=C1
• Uses: A new pyridone alkaloid as an intermediate in the synthesis of Piperlongumine (P482850).

Technology Process of 5,6-Dihydropyridin-2(1H)-one

There total 21 articles about 5,6-Dihydropyridin-2(1H)-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: 98.0%

6-oxo-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (128372-89-4) → 5,6-dihydro-2(1H)-pyridinone (6052-73-9)

Guidance literature:

With hydrogenchloride; In methanol; water; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1039/c6ob01160h

Reference yield: 97.7%

3-(phenylselanyl)-1-(trimethylsilyl)piperidin-2-one → 5,6-dihydro-2(1H)-pyridinone (6052-73-9)

Guidance literature:

With dihydrogen peroxide; In tetrahydrofuran; at 0 - 20 ℃; for 2h;

DOI:10.1021/acs.jmedchem.7b01096

Reference yield: 94.0%

(E)-N-(but-3-en-1-yl)but-2-enamide → 5,6-dihydro-2(1H)-pyridinone (6052-73-9)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 2h; Reflux;

DOI:10.1002/cmdc.201402292

upstream raw materials:

(E)-2,4-pentadienoic acid

1-(trimethylsilyl)piperidin-2-one

3-(phenylthio)piperidin-2-one

1-(methoxymethyl)-3-(phenylthio)piperidin-2-one

Downstream raw materials:

piperlongumine

(R)-4-(4-chlorophenyl)-2-piperidinone

1-nosyl-5,6-dihydropyridin-2(1H)-one

C₃₃H₃₆N₂O₉

Refernces

• 1、 -. "Piperlongumine derivative as well as preparation method and application thereof". Paragraph 0033; 0038. . Retrieved 2021/01/28.
• 2、 Hsu, Pei-Ling,Lee, Kuo-Hsiung,Li, Yangyang,Ling, Yong,Liu, Ji,Meng, Chi,Morris-Natschke, Susan L.,Qian, Jianqiang,Xu, Zhongyuan,Yang, Yumin,Zhang, Yanan,Zhu, Weizhong. "Design and synthesis of benzylidenecyclohexenones as TrxR inhibitors displaying high anticancer activity and inducing ROS, apoptosis, and autophagy". . . Retrieved 2020/07/31.