Pitofenone

Base Information

• Chemical Name: Pitofenone
• CAS No.: 54063-52-4
• Molecular Formula: C22H25 N O4
• Molecular Weight: 367.445
• Hs Code.: 2933399090
• UNII: M09N8K7YJY
• DSSTox Substance ID: DTXSID6048381
• Nikkaji Number: J12.332C
• Wikipedia: Pitofenone
• Wikidata: Q7199015
• NCI Thesaurus Code: C73177
• Metabolomics Workbench ID: 155751
• ChEMBL ID: CHEMBL2104821
• Mol file: 54063-52-4.mol

Synonyms:baralginketone;methyl 2-(4-(2-piperid-1-ylethoxy)benzoyl) benzoate;pitofenone;pitofenone hydrochloride;pitophenon

Chemical Property of Pitofenone

Chemical Property:

• Vapor Pressure: 1.35E-10mmHg at 25°C
• Boiling Point: 512°Cat760mmHg
• PKA: 8.51±0.10(Predicted)
• Flash Point: 263.4°C
• PSA: 55.84000
• Density: g/cm³
• LogP: 3.50680
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 367.17835828
• Heavy Atom Count: 27
• Complexity: 481

Purity/Quality:

99%, ^*data from raw suppliers

Pitofenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC=CC=C1C(=O)C2=CC=C(C=C2)OCCN3CCCCC3

Technology Process of Pitofenone

There total 7 articles about Pitofenone 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: 91.0%

1-piperidinoethanol (3040-44-6) + methanol (67-56-1) + 2-(4-bromobenzoyl)benzoic acid (2159-40-2) → 2-methoxycarbonyl-4'-(2-piperidinoethyloxy)benzophenone (54063-52-4)

Guidance literature:

1-piperidinoethanol; With sodium hydride; In tetrahydrofuran; for 0.5h; Reflux;

methanol; 2-(4-bromobenzoyl)benzoic acid; With sodium hydride; In tetrahydrofuran; at 20 ℃;

With thionyl chloride; at 0 - 20 ℃;

DOI:10.1021/ol400919u

Reference yield: 88.0%

2-(4-hydroxybenzoyl)benzoic acid methyl ester (21147-23-9) + N-chloroethylpiperidine hydrochloride (2008-75-5) → 2-methoxycarbonyl-4'-(2-piperidinoethyloxy)benzophenone (54063-52-4)

Guidance literature:

With potassium carbonate; In ethyl acetate; at 60 ℃; for 15h;

DOI:10.1021/jacs.6b13113

Reference yield: 85.0%

piperidine (110-89-4) + methyl 2-(4-(2-bromoethoxy)benzoyl)benzoate → 2-methoxycarbonyl-4'-(2-piperidinoethyloxy)benzophenone (54063-52-4)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 50 ℃; for 1h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.joc.6b01064

upstream raw materials:

2-(piperidin-4-yl)ethyl chloride

2-(4-hydroxybenzoyl)benzoic acid methyl ester

1-piperidinoethanol

methanol

Downstream raw materials:

2-[4-(2-piperidino-ethoxy)-benzoyl]-benzoic acid

Refernces

• 1、 Sagadevan, Arunachalam,Charpe, Vaibhav Pramod,Ragupathi, Ayyakkannu,Hwang, Kuo Chu. "Visible Light Copper Photoredox-Catalyzed Aerobic Oxidative Coupling of Phenols and Terminal Alkynes: Regioselective Synthesis of Functionalized Ketones via C C Triple Bond Cleavage". . p. 2896 - 2899. Retrieved 2017/03/11.
• 2、 Miao, Jinmin,Ge, Haibo. "Palladium-catalyzed chemoselective decarboxylative ortho acylation of benzoic acids with α-oxocarboxylic acids". supporting information. p. 2930 - 2933. Retrieved 2013/07/26.