5-{[tert-Butyl(dimethyl)silyl]oxy}cyclohex-2-en-1-one

Base Information

Chemical Name:5-{[tert-Butyl(dimethyl)silyl]oxy}cyclohex-2-en-1-one
CAS No.:225793-33-9
Molecular Formula:C₁₂H₂₂O₂Si
Molecular Weight:226.391
Hs Code.:
DSSTox Substance ID:DTXSID60437898

Synonyms:225793-33-9;SCHEMBL2943294;DTXSID60437898;FT-0654325;A816270;5-[tert-butyl(dimethyl)silyl]oxy-1-cyclohex-2-enone;5-[tert-butyl(dimethyl)silyl]oxycyclohex-2-en-1-one;5-{[tert-Butyl(dimethyl)silyl]oxy}cyclohex-2-en-1-one

Suppliers and Price of 5-{[tert-Butyl(dimethyl)silyl]oxy}cyclohex-2-en-1-one

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 3 raw suppliers

Chemical Property of 5-{[tert-Butyl(dimethyl)silyl]oxy}cyclohex-2-en-1-one

Chemical Property:

Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:226.138906475
Heavy Atom Count:15
Complexity:274

Purity/Quality:: 97% ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC(C)(C)[Si](C)(C)OC1CC=CC(=O)C1

Technology Process of 5-{[tert-Butyl(dimethyl)silyl]oxy}cyclohex-2-en-1-one

There total 5 articles about 5-{[tert-Butyl(dimethyl)silyl]oxy}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: 88.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 406460-97-7
(5S)-5-hydroxycyclohex-2-enone

: 225793-33-9
(5R)-5-(tert-butyldimethylsiloxy)cyclohex-2-enone

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 1.5h; optical yield given as %ee;
DOI:10.1021/ol801392d

Reference yield:

: 3-(tert-butyl-dimethyl-silanyloxy)-5-chloro-cyclohexanone

: 225793-33-9
(5R)-5-(tert-butyldimethylsiloxy)cyclohex-2-enone

Guidance literature:: With sodium acetate; In methanol; for 1h; Ambient temperature;
DOI:10.1021/ja9843122

Reference yield:

: 130158-22-4
ethyl (S)-3-((tert-butyldimethylsilyl)oxy)-4-iodobutanoate

: 225793-33-9
(5R)-5-(tert-butyldimethylsiloxy)cyclohex-2-enone

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) CuI, 2.) N,N'-(dimethylpropylene)urea, (EtO)3P / 1.) THF, -35 deg C, 15 min, 2.) THF, from -35 deg C to RT

2: Ti(Oi-Pr)4, i-PrMgCl / diethyl ether / a) -45 to -40 deg C, 1 h, b) from -40 deg C to RT, 90 min, c) RT, 2 h

3: FeCl₃, pyridine / dimethylformamide / 0.5 h / Ambient temperature

4: NaOAc / methanol / 1 h / Ambient temperature

With pyridine; titanium(IV) isopropylate; copper(l) iodide; 4,4,5-trimethyl-2-imidazolidinone; isopropylmagnesium chloride; sodium acetate; iron(III) chloride; triethyl phosphite; In methanol; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/ja9843122