(1,2-diphenyl-2-trimethylsilylethyl)-trimethylsilane | 18586-58-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1,2-diphenyl-2-trimethylsilylethyl)-trimethylsilane
• 英文别名: meso-hexa-Si-methyl-Si,Si'-bibenzyl-α,α'-diyl-bis-silane；erythro-1,2-diphenyl-1,2-bis(trimethylsilyl)ethane；(+/-)-1,2-bis(trimethylsilyl)-1,2-diphenylethane；DL-1,2-diphenyl-1,2-bis-(trimethylsilyl)ethane；dl-1,2-bis(trimethylsilyl)-1,2-diphenylethane
• CAS: 18586-58-8；24894-88-0；62120-71-2
• 化学式: C₂₀H₃₀Si₂
• 分子量: 326.629
• InChiKey: GYDXRACZXACESB-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.31
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  苄基三甲基硅烷 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 乙腈 、 苯 为溶剂， 反应 38.0h， 生成 (1,2-diphenyl-2-trimethylsilylethyl)-trimethylsilane
  参考文献：
  名称：

  Electrochemical Formation and Dimerization of α-Substituted Benzyl Radicals. Steric Effects on Dimerization

  摘要：

  DOI：

  10.1021/jo951577f

文献信息

• Copper-Catalyzed Twofold Silylmetalation of Alkynes
  作者：Hiroki Yamagishi、Jun Shimokawa、Hideki Yorimitsu

  DOI：10.1055/s-0037-1611869

  日期：2019.8

  The first twofold silylmetalation across a C≡C triple bond was achieved. In the presence of a catalytic amount of copper cyanide, diarylacetylenes were converted into 1,2-dimetalated 1,2-disilyl-1,2-diarylethanes on treatment with silylpotassium species generated in situ from disilane and t-BuOK. The dimetalated species were subsequently protonated to yield a series of 1,2-disilyl-1,2-diarylethanes.

  首次实现了对C≡C三键的双重硅基金属化反应。在存在少量铜氰化物的情况下，二芳基乙炔在与从二硅烷和t-BuOK原位生成的硅基钾物种反应时转化为1,2-二金属化的1,2-二硅基-1,2-二芳基乙烷。随后，这些二金属化物种被质子化，生成了一系列1,2-二硅基-1,2-二芳基乙烷。
• Design, Synthesis, and Electrochemical Behavior of New Electronic Systems Involving<i>σ</i>,<i>σ</i>- and<i>σ</i>,<i>π</i>-Interaction
  作者：Keiji Nishiwaki、Jun-ichi Yoshida

  DOI：10.1246/cl.1996.787

  日期：1996.9

  2-diphenylethane and its homologues were synthesized and the studies on their electochemical behavior revealed that there is definite interaction between the σ,π-interaction system (the C-Si bonds and the benzene rings) and the σ,σ-interaction system (the neighboring C-Si bonds) which causes significant decrease of the oxidation potentials.

  合成了 1,2-双（三甲基甲硅烷基）-1,2-二苯基乙烷及其同系物，对其电化学行为的研究表明，σ,π-相互作用体系（C-Si 键和苯环）之间存在明确的相互作用。 ) 和 σ,σ-相互作用系统（相邻的 C-Si 键）导致氧化电位显着降低。
• SET and Exciplex Pathways in the Photochemical Reactions between Aromatic Ketones and Benzylsilane and Stannane Derivatives
  作者：Laura Cermenati、Mauro Freccero、Paolo Venturello、Angelo Albini

  DOI：10.1021/ja00135a003

  日期：1995.8

  The photochemical reaction of alpha,alpha,alpha-trifluoroacetophenone (TFA), benzophenone, and p-cyanoacetophenone with benzyltrimethylsilane in MeCN involves hydrogen transfer from the benzylic position. Desilylation occurs as a minor process only in the case of TFA (but it increases greatly in the presence of MeOH or LiClO4). The final products result from the statistical recombination of the benzyl and ketyl radicals. Further cases of intramolecular selectivity studied are p-methylbenzyl- and p-methoxybenzyltrimethylsilane (the latter substrate undergoes mainly C-Si bond cleavage in the reaction with TFA) as well as benzyltributylstannane (only destannylation observed with all ketones). Product studies are complemented by the determination of relevant kinetic parameters through steady-state and flash-photolysis experiments. The results are explained in terms of hydrogen transfer proceeding from an exciplex and desilylation from the solvent separated radial ion pair. The latter species predominates when Delta G(et) < -10 kcal mol(-1).
• Huang,H.H., Australian Journal of Chemistry, 1976, vol. 29, p. 2415 - 2422
  作者：Huang,H.H.

  DOI：——

  日期：——