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

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

Uses

Used in Organic Synthesis:
1-Cyclohexenyloxytrimethylsilane is used as an intermediate for the synthesis of complex organic compounds, including natural products. Its cyclohexenyloxy group provides a handle for further functionalization and modification, facilitating the construction of intricate molecular architectures.
Used in Pharmaceutical Industry:
1-Cyclohexenyloxytrimethylsilane is utilized as a pharmaceutical intermediate, playing a crucial role in the development of new drugs and therapeutic agents. Its ability to be incorporated into complex molecular frameworks makes it a valuable component in the design and synthesis of bioactive molecules with potential medicinal applications.

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

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 108-94-1 cyclohexanone 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 1206-46-8 trimethyl(pentafluorophenyl)silane 
• 7449-74-3 N-methyl-N-trimethylsilylacetamide 
• 1424-22-2 1-cyclohexenyl acetate 
• 930-68-7 cyclohexenone 
• 63408-33-3 2-Trimethylsilanyl-octane-1,2-diol 
• 43112-38-5 3-(trimethylsilyl)-2-oxazolidinone 
• 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 

Downstream Products

• 15210-04-5 ethyl 2-hydroxy-2-(2-oxocyclohexyl)propanoate 
• 1080-41-7 diethyl (2-oxocyclohexyl)phosphonate 
• 6126-53-0 2-(2-oxopropyl)cyclohexanone 
• 55339-76-9 2-((E)-2-Trimethylsilanyloxy-propenyl)-cyclohexanone 
• 57146-98-2 2-<(1-Hydroxy-1-methyl-2,2-dimethyl-2-aethoxycarbonyl)-aethyl>-cyclohexanon-(1) 
• 5441-54-3 2-tert-Pentylcyclohexanon 
• 1728-46-7 2-tert-butylcyclohexanone 
• 67938-20-9 (2-Butylsulfanyl-cyclohexyloxy)-trimethyl-silane 
• 4736-41-8 2-(1,1,2-Trimethylpropyl)cyclohexanon 
• 72216-41-2 2-(1-Methyl-1-propylbutyl)cyclohexanon 
• 29943-11-1 2-(2'-Oxobutyl)-cyclohexanon 
• 61235-08-3 2-(2-Acetoxy-1-hydroxy-1-methyl)-ethyl-cyclohexanon-⁽¹⁾ 
• 57147-03-2 2-(4-Methoxycarbonyl-1-hydroxy-1-methyl)-butyl-cyclohexanon-⁽¹⁾ 
• 72216-43-4 2-(1-Methyl-1-cyclopentyl)cyclohexanon 

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.

Nucleophilic Attack on Nitrogen in Tetrazines by Silyl-Enol Ethers

The nucleophilic addition of silyl-enol ethers to nitrogen in 3-monosubstituted s-tetrazines mediated by BF3 is reported. The preference for this azaphilic addition over the usually observed inverse electron demand Diels-Alder reactions was evaluated theoretically and corroborated by experiments. The substrate dependency of this unusual reaction was rationalized by determination of the activation barriers and on the basis of the activation strain model by employing density functional theory.

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.

Last of the gem-Difluorocycloalkanes 2: Synthesis of Fluorinated Cycloheptane Building Blocks

The gem-difluorocycloalkane family was extended to all possible regioisomers of the gem-difluorocycloheptane, monofunctionalized by carboxilic-, amino- or keto- group, that were synthesized on a multigram scale. The preparation of the corresponding building blocks was achieved from readily accessible starting materials either via six-membered ring homologation or deoxofluorination of the appropriate seven-membered cyclic ketones.

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.

Direct C-H α-Arylation of Enones with ArI(O2CR)2 Reagents

α-Arylation of α,β-unsaturated ketones constitutes a powerful synthetic transformation. It is most commonly achieved via cross-coupling of α-haloenones, but this stepwise strategy requires prefunctionalized substrates and expensive catalysts. Direct enone C-H α-arylation would offer an atom- and step-economical alternative, but such reports are scarce. Herein we report the metal-free direct C-H arylation of enones mediated by hypervalent iodine reagents. The reaction proceeds via a reductive iodonium Claisen rearrangement of in situ-generated β-pyridinium silyl enol ethers. The aryl groups are derived from ArI(O2CCF3)2 reagents, which are readily accessed from the parent iodoarenes. The reaction is tolerant of a wide range of substitution patterns, and the incorporated arenes maintain the valuable iodine functional handle. Mechanistic investigations implicate arylation via an umpoled "enolonium" species and show that the presence of a β-pyridinium moiety is critical for the desired C-C bond formation.

Manganese-Catalyzed Electrochemical Deconstructive Chlorination of Cycloalkanols via Alkoxy Radicals

A manganese-catalyzed electrochemical deconstructive chlorination of cycloalkanols has been developed. This electrochemical method provides access to alkoxy radicals from alcohols and exhibits a broad substrate scope, with various cyclopropanols and cyclobutanols converted into synthetically useful β- and γ-chlorinated ketones (40 examples). Furthermore, the combination of recirculating flow electrochemistry and continuous inline purification was employed to access products on a gram scale.

Metal complex, organic electroluminescent device, organic electroluminescent material

The invention relates to a metal complex, an organic electroluminescent device containing the metal complex and an organic electroluminescent material. The metal complex has a molecular formula of M(LA)(m-n)(LC)n, wherein M is metal element Ir, m is the oxidation valence state of metal M, n is an integer of 1 or more and is less than m. The electroluminescent device containing the metal complex emits red light, and has a high external quantum efficiency; and the material has good thermal stability, the service life of the device can be prolonged, the material is easily prepared and purified and can be used as an ideal choice for a luminescent material of the organic electroluminescent device.

C?O coupling of Malonyl Peroxides with Enol Ethers via [5+2] Cycloaddition: Non-Rubottom Oxidation

Malonyl peroxides act both as oxidants and reagents for C?O coupling in reactions with methyl and silyl enol ethers. In the proposed conditions, the oxidative C?O coupling of malonyl peroxides with enol ethers selectively proceeds, bypassing the traditional Rubottom hydroxylation of enol ethers by peroxides. It was observed that the oxidative [5+2] cycloaddition of malonyl peroxides and enol ethers is the key stage of the discovered process. Oxidative C?O coupling of silyl enol ethers leads to the formation of α-acyloxyketones with a free carboxylic acid group. A specially developed preparative one-pot procedure transforms ketones via silyl enol ethers formation and the following coupling into α-acyloxyketones with yields 35–88%. The acid-catalyzed coupling with methyl enol ethers gives remarkable products while retaining the easily oxidizable enol fragment. Furthermore, these molecules contain a free carboxylic acid group, thus these nontrivial products contain two usually incompatible acid and enol ether groups. (Figure presented.).

Ni-Catalyzed β-Alkylation of Cyclopropanol-Derived Homoenolates

Metal homoenolates are valuable synthetic intermediates which provide access to β-functionalized ketones. In this report, we disclose a Ni-catalyzed β-alkylation reaction of cyclopropanol-derived homoenolates using redox-active N-hydroxyphthalimide (NHPI) esters as the alkylating reagents. The reaction is compatible with 1°, 2°, and 3° NHPI esters. Mechanistic studies imply radical activation of the NHPI ester and 2e β-carbon elimination occurring on the cyclopropanol.