17156-65-9

Usage

Uses

Used in Chemical Synthesis:
(METHYLDIPHENYLSILYL)ACETYLENE is used as a synthetic building block for the creation of diphenylmethylsilyl-substituted isoxazoles. This is achieved through a [2+3] cycloaddition reaction with nitrile oxides, which allows for the formation of complex molecular structures with potential applications in various fields.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (METHYLDIPHENYLSILYL)ACETYLENE may be utilized as a key intermediate in the synthesis of novel drug candidates. Its unique structure can be exploited to design and develop new molecules with specific biological activities, potentially leading to the discovery of new therapeutic agents.
Used in Materials Science:
(METHYLDIPHENYLSILYL)ACETYLENE could also be employed in the field of materials science, where its properties can be harnessed to create new materials with tailored characteristics. For instance, its incorporation into polymers or other materials could lead to improved mechanical, thermal, or electrical properties, depending on the desired application.

InChI:InChI=1/C15H14Si/c1-3-16(2,14-10-6-4-7-11-14)15-12-8-5-9-13-15/h1,4-13H,2H3

Upstream product

• 144-79-6 chloromethyldiphenylsilane 
• 74-86-2 acetylene 
• 917-54-4 methyllithium 

Downstream Products

• 102-07-8 bis(diphenyl)urea 
• 1438770-56-9 1,3,5-tris[methyl(diphenyl)silyl]-2-phenylbenzene 
• 1226762-22-6 (S)-1-(methyldiphenylsilyl)deca-1,4-diyn-3-ol 
• 166905-91-5 (η5-C5H5)carbonyltungsten(NO)(η1-vinylidene) 

Relevant academic research and scientific papers

Three-coordinate copper(II) alkynyl complex in C-C bond formation: The sesquicentennial of the glaser coupling

Copper(II) alkynyl species are proposed as key intermediates in numerous Cu-catalyzed C-C coupling reactions. Supported by a β-diketiminate ligand, the three-coordinate copper(II) alkynyl [CuII]-C≡CAr (Ar = 2,6-Cl2C6H3) forms upon reaction of the alkyne H-C≡CAr with the copper(II) tertbutoxide complex [CuII]-OtBu. In solution, this [CuII]-C≡CAr species cleanly transforms to the Glaser coupling product ArC≡C-C≡CAr and [CuI](solvent). Addition of nucleophiles R′C≡C-Li (R′ = aryl, silyl) and Ph-Li to [CuII]-C≡CAr affords the corresponding Csp-Csp and Csp-Csp2 coupled products RC≡C-C≡CAr and Ph-C≡CAr with concomitant generation of [CuI](solvent) and {[CuI]-C≡CAr}-, respectively. Supported by density functional theory (DFT) calculations, redox disproportionation forms [CuIII](C≡CAr)(R) species that reductively eliminate R-C≡CAr products. [CuII]-C≡CAr also captures the trityl radical Ph3C· to give Ph3C-C≡CAr. Radical capture represents the key Csp-Csp3 bond-forming step in the copper-catalyzed C-H functionalization of benzylic substrates R-H with alkynes H-C≡CR′ (R′ = (hetero)aryl, silyl) that provide Csp-Csp3 coupled products R-C≡CR via radical relay with tBuOOtBu as oxidant.

Pericyclynosilanes: Synthesis of a New Class of Cyclic Organosilicon Compounds

The pericyclynosilanes, systematically known as cyclopoly(silapropynylenes), (R2SiCC)n (where R=Me or Ph, n>/=5) have been synthesised, in high yield, by the reaction of the dilithium derivatives of diorganodiethynylsilanes with the corresponding diorganodichlorosilanes, and the dodecamethyl (n=6) and dodecaphenyl (n=6) derivatives have been isolated and fully characterised; when the organic substituents present in the diorganodiethynylsilane differ from those of the diorganodichlorosilane, a redistribution reaction is observed, leading to a product in which the organosilicon units are randomly distributed.

SILICON-DIRECTED NAZAROV CYCLIZATIONS - IV FURTHER STUDIES IN STEREOCHEMICAL CONTROL

The silicon-directed Nazarov cyclization was shown to proceed with good to excellent stereoselectivity in cyclohexenyl systems bearing a variety of ring substituents.In all cases the trans family of isomers predominated, and cis ring-fused products were f