6651-36-1

Basic information

• Product Name: 1-Cyclohexenyloxytrimethylsilane
• Synonyms: (1-cyclohexen-1-yloxy)trimethyl-silan;1-(trimethylsiloxy)-cyclohexene1,1,1,3,3,3-;1-CYCLOHEXENYLOXYTRIMETHYLSILANE;(1-CYCLOHEXEN-1-YLOXY)TRIMETHYLSILANE;1-(TRIMETHYLSILOXY)CYCLOHEXENE;1-TRIMETHYLSILYLOXYCYCLOHEXENE;(CYCLOHEXENYLOXY)TRIMETHYLSILANE;CYCLOHEXANONE ENOL TRIMETHYLSILYL ETHER
• CAS NO: 6651-36-1
• Molecular Formula: C₉H₁₈OSi
• Molecular Weight: 170.32
• EINECS: 229-675-1
• Product Categories: Monoalkoxysilanes;Si (Classes of Silicon Compounds);Silicon Compounds (for Synthesis);Si-O Compounds;Synthetic Organic Chemistry
• Mol File: 6651-36-1.mol
• Article Data: 100

Chemical Properties

• Boiling Point: 64-65 °C15 mm Hg(lit.)
• Flash Point: 108 °F
• Appearance: clear yellow liquid
• Density: 0.875 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.52mmHg at 25°C
• Refractive Index: n20/D 1.447(lit.)
• Storage Temp.: 2-8°C
• Solubility: Not miscible or difficult to mix.
• Sensitive: Moisture Sensitive
• BRN: 1859394
• CAS DataBase Reference: 1-Cyclohexenyloxytrimethylsilane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Cyclohexenyloxytrimethylsilane(6651-36-1)
• EPA Substance Registry System: 1-Cyclohexenyloxytrimethylsilane(6651-36-1)

Safety Data

• Hazard Codes: F
• Statements: 10
• Safety Statements: 16
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 10-21
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 6651-36-1(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow liquid

Uses

1-(Trimethylsiloxy)cyclohexene is used as intermediate to complex compounds, including natural products. It is also used as a pharmaceutical intermediate.

General Description

1-(Trimethylsiloxy)cyclohexene undergoes Michael addition reaction with methyl vinyl ketone in the presence of dibutyltin bis(triflate).

InChI:InChI=1/C9H18OSi/c1-11(2,3)10-9-7-5-4-6-8-9/h7H,4-6,8H2,1-3H3

Upstream product

• 1056477-06-5 2-bromocyclohexanone 
• 43112-38-5 3-(trimethylsilyl)-2-oxazolidinone 
• 108-94-1 cyclohexanone 
• 123-19-3 4-heptanone 
• 2857-97-8 trimethylsilyl bromide 
• 16029-98-4 trimethylsilyl iodide 
• 2083-91-2 N,N-Dimethyltrimethylsilylamine 
• 34880-70-1 [1-methoxyprop-1-enyloxy]trimethylsilane 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 115262-00-5 [chloro(difluoro)methyl]trimethylsilane 
• 120-92-3 cyclopentanone 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 75-77-4 chloro-trimethyl-silane 
• 14627-81-7 di-tert-butylmagnesium 

Downstream Products

• 72216-41-2 2-(1-Methyl-1-propylbutyl)cyclohexanon 
• 62183-29-3 1-pivaloyloxy-1-cyclohexene 
• 60669-65-0 2-(1-hydroxy-3-phenylpropyl)cyclohexan-1-one 
• 147933-03-7 3-chloro-4-(2-oxocyclohexyl)cyclobut-3-ene-1,2-dione 
• 147932-91-0 2-(2,3-dichloro-1-hydroxy-4-oxocyclobut-2-enyl)cyclohexanone 
• 126937-72-2 2-(1-Hydroxy-3-phenyl-prop-2-ynyl)-cyclohexanone 
• 126937-72-2 2-(1-Hydroxy-3-phenyl-prop-2-ynyl)-cyclohexanone 
• 55705-17-4 α-(phenylsulfinyl)cyclohexanone 
• 7153-14-2 2-Buthylidenecyclohexanone 
• 174621-33-1 2-(1-methoxybutyl)-1-cyclohexanone 
• 74209-77-1 2-(1-Methoxy-butyl)-cyclohexanone 
• 74209-77-1 2-(1-Methoxy-butyl)-cyclohexanone 
• 74209-77-1 erythro-2-(1-methoxybutyl)cyclohexanone 
• 74209-77-1 threo-2-(1-methoxybutyl)cyclohexanone 

Relevant articles and documents

Strain-release electrophilic activation via E-cycloalkenones

UVA irradiation (ca. 350 nm) of a mixture of cyclic enones and nitrogen heterocycles leads to efficient formation of the 1,4-adducts in a variety of solvents, at room temperature. These reactions likely proceed through strained E-cycloalkenone intermediates, as suggested by lowtemperature generation/trapping experiments monitored by 1H NMR. These results demonstrate that E-cycloalkenones are good electrophiles despite their known tendency to favor a conformation in which the carbonyl is not fully conjugated with the double bond.

Boron Trifluoride-Mediated Cycloaddition of 3-Bromotetrazine and Silyl Enol Ethers: Synthesis of 3-Bromo-pyridazines

Pyridazines are important scaffolds for medicinal chemistry or crop protection agents, yet the selective preparation of 3-bromo-pyridazines with high regiocontrol remains difficult. We achieved the Lewis acid-mediated inverse electron demand Diels-Alder reaction between 3-monosubstituted s-tetrazine and silyl enol ethers and obtained functionalized pyridazines. In the case of 1-monosubstituted silyl enol ethers, exclusive regioselectivity was observed. Downstream functionalization of the resulting 3-bromo-pyridazines was demonstrated utilizing several cross-coupling protocols to synthesize 3,4-disubstituted pyridazines with excellent control over the substitution pattern.

Three-Component Coupling of Acyl Fluorides, Silyl Enol Ethers, and Alkynes by P(III)/P(V) Catalysis

We report herein on the phosphine-catalyzed hydrovinylation reaction by three-component coupling of acyl fluorides, silyl enol ethers, and alkynoates. The key to the success of the reaction is the formal transmetalation between pentacoordinate P(V) species (i.e., fluorophosphorane) and a silyl enol ether, which allows for C-C bond formation between the polarity-mismatched sites. The bond formation that cannot be attained even by transition metal catalysis is accomplished by a P(III)/P(V) manifold.