3-[(Trimethylsilyl)ethynyl]cyclohex-2-en-1-one

Base Information

• Chemical Name: 3-[(Trimethylsilyl)ethynyl]cyclohex-2-en-1-one
• CAS No.: 124267-25-0
• Molecular Formula: C11H16OSi
• Molecular Weight: 192.333
• DSSTox Substance ID: DTXSID20561784
• Nikkaji Number: J845.226A
• Wikidata: Q82445647
• Mol file: 124267-25-0.mol

Synonyms:124267-25-0;3-[(Trimethylsilyl)ethynyl]cyclohex-2-en-1-one;DTXSID20561784

Chemical Property of 3-[(Trimethylsilyl)ethynyl]cyclohex-2-en-1-one

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 192.097041664
• Heavy Atom Count: 13
• Complexity: 306

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)C#CC1=CC(=O)CCC1

Technology Process of 3-[(Trimethylsilyl)ethynyl]cyclohex-2-en-1-one

There total 10 articles about 3-[(Trimethylsilyl)ethynyl]cyclohex-2-en-1-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: 93.0%

1-((trimethylsilyl)ethynyl)cyclohex-2-en-1-ol (1206544-09-3) → 3-[(trimethylsilyl)ethynyl]-2-cyclohexen-1-one (124267-25-0)

Guidance literature:

With dipyridinium dichromate; In dichloromethane; at 20 ℃; for 36h; Inert atmosphere;

DOI:10.1021/acs.joc.9b01403

Reference yield: 88.0%

3-oxocyclohex-1-en-1-yl 4-methylbenzenesulfonate (77708-66-8) + trimethylsilylacetylene (1066-54-2) → 3-[(trimethylsilyl)ethynyl]-2-cyclohexen-1-one (124267-25-0)

Guidance literature:

With N,N-dimethyl acetamide; palladium diacetate; triphenylphosphine; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1016/S0040-4039(02)01447-8

Reference yield: 82.0%

3-isobutoxycyclohex-2-en-1-one (23074-59-1) + lithium trimethylsilylacetylenide (54655-07-1) → 3-[(trimethylsilyl)ethynyl]-2-cyclohexen-1-one (124267-25-0)

Guidance literature:

In tetrahydrofuran; 1) 0.5 h, -78 deg C, 1 h, RT;

DOI:10.1021/jo00290a030

upstream raw materials:

3-isobutoxycyclohex-2-en-1-one

lithium trimethylsilylacetylenide

1,3-cylohexanedione

3-oxocyclohex-1-en-1-yl 4-methylbenzenesulfonate

Downstream raw materials:

3-ethynyl-2-cyclohexen-1-one

3-(deuterioethynyl)-2-cyclohexenone

(E)-3-(prop-1-en-1-yl)cyclohex-2-en-1-one

3-propenyl-2-cyclohexenone