1-(Trimethylsiloxy)cyclohexene is used as intermediate to complex compounds, including natural products. It is also used as a pharmaceutical intermediate.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
1-(Trimethylsiloxy)cyclohexene is used as intermediate to complex compounds, including natural products. It is also used as a pharmaceutical intermediate.
Solubility
Not miscible or difficult to mix.
Notes
Keep container tightly sealed. Store in cool, dry conditions in well sealed containers. Incompatible with oxidizing agents. It is sensitive to moisture. Store under dry inert gas.
RUO – Research Use Only
Yea Shun Cheng.; Eugene Ho.; Patrick S. Mariano.; Herman L. Ammon. Mechanistic aspects of the boron trifluoride catalyzed, intermolecular Diels-Alder cycloaddition of an unactivated 2-aza 1,3-diene with electron-donating-substituted dienophiles. J. Org. Chem. 1985, 50 (26), 5678-5686.
Keiji Tanino.; Tadashi Shimizu.; Motoki Miyama.; Isao Kuwajima. A Novel [5+2] Cycloaddition Reaction Using a Dicobalt Acetylene Complex. J. Am. Chem. Soc. 2002, 122 (25), 6116-6117.
Silyl enol ethers undergo crossed aldol condensations with aldehydes and ketones: J. Am. Chem. Soc., 96, 7503 (1974); for tabulated results, see: Org. Synth. Coll., 8, 323 (1993):
Condensation with aldehydes is also promoted by F-, particularly TBAF: J. Org. Chem., 48, 932 (1983).
The Lewis acid-catalyzed condensation with nitroalkenes leads to 1,4-diketones: J. Am. Chem. Soc., 98, 4679 (1976); Org. Synth. Coll, 7, 414 (1990).
For reviews of the chemistry of silyl enol ethers, see: Synthesis, 91 (1977); 85 (1983).