3,4-Diphenylbut-3-en-2-one

Base Information

• Chemical Name: 3,4-Diphenylbut-3-en-2-one
• CAS No.: 1722-69-6
• Molecular Formula: C16H14 O
• Molecular Weight: 222.287
• European Community (EC) Number: 651-741-7
• DSSTox Substance ID: DTXSID801344035
• ChEMBL ID: CHEMBL2133310
• Mol file: 1722-69-6.mol

Synonyms:3,4-diphenylbut-3-en-2-one;MLS003389307;1722-69-6;SCHEMBL5183481;CHEMBL2133310;DTXSID801344035;SMR002048962

Chemical Property of 3,4-Diphenylbut-3-en-2-one

Chemical Property:

• Vapor Pressure: 1.38E-05mmHg at 25°C
• Boiling Point: 367.3°Cat760mmHg
• Flash Point: 139.6°C
• Density: 1.078g/cm³
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 222.104465066
• Heavy Atom Count: 17
• Complexity: 278

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C(=CC1=CC=CC=C1)C2=CC=CC=C2

Technology Process of 3,4-Diphenylbut-3-en-2-one

There total 32 articles about 3,4-Diphenylbut-3-en-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: 95.0%

(Z)-3-bromo-4-phenyl-3-buten-2-one (22965-96-4) + phenylboronic acid (98-80-6) → (E)-1,2-diphenylbut-1-en-3-one (38661-88-0,1722-69-6,54963-40-5)

Guidance literature:

With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); triethylamine; In tetrahydrofuran; water; at 20 ℃; Inert atmosphere;

DOI:10.1021/ja102689e

Reference yield: 86.0%

benzaldehyde (100-52-7) + 1-phenyl-acetone (103-79-7,136675-26-8) → 3,4-diphenylbut-3-en-2-one (1722-69-6)

Guidance literature:

With piperidine; In toluene; for 12h; Reflux; Dean-Stark;

DOI:10.1021/acs.orglett.0c00588

Reference yield: 80.0%

diphenyliodonium chloride (1483-72-3) + Triphenyl-phenylethynyl-stannane (1247-08-1) + acetyl chloride (75-36-5) → (E)-1,2-diphenylbut-1-en-3-one (38661-88-0,1722-69-6,54963-40-5)

Guidance literature:

Triphenyl-phenylethynyl-stannane; With Schwartz's reagent; In tetrahydrofuran; at 20 ℃; for 0.5h;

acetyl chloride; With copper(l) iodide; at 20 ℃; for 8h;

diphenyliodonium chloride; With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1080/00397910008086964

upstream raw materials:

4-chloro-3,4-diphenyl-butan-2-one

C₁₈H₁₈OS

benzaldehyde

1-phenyl-acetone

Downstream raw materials:

(E)-3-tert-butyl-1,2-diphenyl-1,3-butadiene

3,4,5,6-Tetraphenyl-octane-2,7-dione

1-Benzyl-4-(3-oxo-1,2-diphenyl-butyl)-1,4-dihydro-pyridine-3-carboxylic acid amide

1,1'-dibenzyl-1,4,1',4'-tetrahydro-[4,4']bipyridinyl-3,3'-dicarboxylic acid diamide

Refernces

• 1、 Hao, Hong-Yan,Mao, Yang-Jie,Xu, Zhen-Yuan,Lou, Shao-Jie,Xu, Dan-Qian. "Selective Cross-Dehydrogenative C(sp3)-H Arylation with Arenes". supporting information. p. 2396 - 2402. Retrieved 2020/03/13.
• 2、 Wang, Qingli,Gao, Wenchao,Lv, Hui,Zhang, Xumu. "Enantioselective synthesis of β-substituted chiral allylic amines: Via Rh-catalyzed asymmetric hydrogenation". supporting information. p. 11850 - 11853. Retrieved 2016/10/07.