2-Propyn-1-one, 1-phenyl-3-(trimethylsilyl)-

Base Information

• Chemical Name: 2-Propyn-1-one, 1-phenyl-3-(trimethylsilyl)-
• CAS No.: 13829-77-1
• Molecular Formula: C12H14OSi
• Molecular Weight: 202.328
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID40452140
• Nikkaji Number: J303.534D
• Wikidata: Q82272553
• Mol file: 13829-77-1.mol

Synonyms:13829-77-1;2-Propyn-1-one, 1-phenyl-3-(trimethylsilyl)-;1-phenyl-3-trimethylsilylprop-2-yn-1-one;benzoyltrimethylsilylacetylene;SDK-8;SCHEMBL1712895;DTXSID40452140

Chemical Property of 2-Propyn-1-one, 1-phenyl-3-(trimethylsilyl)-

Chemical Property:

• PSA: 17.07000
• LogP: 2.75010
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 202.081391600
• Heavy Atom Count: 14
• Complexity: 268

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)C#CC(=O)C1=CC=CC=C1

Technology Process of 2-Propyn-1-one, 1-phenyl-3-(trimethylsilyl)-

There total 22 articles about 2-Propyn-1-one, 1-phenyl-3-(trimethylsilyl)- 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%

benzoyl chloride (98-88-4) + trimethylsilylacetylene (1066-54-2) → 3-(trimethylsilyl)-1-phenyl-2-propyn-1-one (13829-77-1)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 20 ℃; for 1h; Reagent/catalyst; Time; Temperature;

DOI:10.1016/j.tet.2013.04.127

Reference yield: 94.0%

benzoyl chloride (98-88-4) + tris(2-(trimethylsilyl)ethynyl)indium (250643-77-7) → 3-(trimethylsilyl)-1-phenyl-2-propyn-1-one (13829-77-1)

Guidance literature:

With mesoporous MCM-41-immobilized phosphine-free heterogeneous palladium⁽⁰⁾-schiff base complex; In tetrahydrofuran; at 68 ℃; for 2h; Inert atmosphere; Green chemistry;

DOI:10.1039/c7ra08355f

Reference yield: 80.0%

benzaldehyde (100-52-7) + trimethylsilylacetylene (1066-54-2) → 3-(trimethylsilyl)-1-phenyl-2-propyn-1-one (13829-77-1)

Guidance literature:

With triethylamine; In tetrahydrofuran; toluene; at 20 ℃; for 24h; Irradiation; Inert atmosphere;

DOI:10.1039/c7nj03557h

upstream raw materials:

N-methoxy-N-methylbenzamide

lithium trimethylsilylacetylenide

1-(trimethylsilyl)-3-phenylprop-1-yne

(trimethylsilylethynyl)tributyltin

Downstream raw materials:

3-Trimethylsilyl-1-phenyl-prop-2-inon-<3,5-dinitro-benzoylhydrazon>

4-Methyl-2-(trimethylsilyl)benzophenon

Piperidine-1-carbodithioic acid (E)-3-oxo-3-phenyl-1-trimethylsilanyl-propenyl ester

1-(N-diethyldithiocarbamoyl)-1-trimethylsilyl-3-phenyl-1-propen-3-one

Refernces

• 1、 Logue,Moore. "". . p. 131. Retrieved 1975.
• 2、 Logue, Marshall W.,Teng, Kelly. "Palladium-Catalyzed Reactions of Acyl Chlorides with (1-Alkynyl)tributylstannanes. A Convenient Synthesis for 1-Alkynyl Ketones". . p. 2549 - 2553. Retrieved 1982.
• 3、 Karpov, Alexei S.,Mueller, Thomas J. J.. "Straightforward Novel One-Pot Enaminone and Pyrimidine Syntheses by Coupling-Addition-Cyclocondensation Sequences". . p. 2815 - 2826. Retrieved 2003.
• 4、 -. "Copper-catalyzed method for preparing aldehyde or ketone compound by oxidizing alcohol with oxygen as oxidizing agent and application". Paragraph 0028-0030; 0064-0069. . Retrieved 2020/08/18.
• 5、 Li, Ming,Zhu, Xin-Yu,Qiu, Yi-Feng,Han, Ya-Ping,Xia, Yu,Wang, Cui-Tian,Li, Xue-Song,Wei, Wan-Xu,Liang, Yong-Min. "Metal-Free Promoted CF2/CF3-Difunctionalization of Unactivated Alkenes". supporting information. p. 2945 - 2950. Retrieved 2019/04/27.