3,4-diphenyl-1,1-diisopropyl-2,5-dilithiosilole | 171967-35-4

• 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: 3,4-diphenyl-1,1-diisopropyl-2,5-dilithiosilole
• CAS: 171967-35-4
• 化学式: C₂₂H₂₄Li₂Si
• 分子量: 330.4
• InChiKey: QBTYTKRSRBVWQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  3,4-diphenyl-1,1-diisopropyl-2,5-dilithiosilole 在 P(furyl)3 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 1,2-二碘乙烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Silole–pyrrole co-oligomers: their synthesis, structure and UV-VIS absorption spectra

  摘要：

  Silole-pyrrole co-oligomers (containing up to nine rings) are synthesized and found to have long UV-VIS absorption maxima in spite of their twisted structures.

  DOI：

  10.1039/cc9960001873
• 作为产物：
  描述：

  diisopropylbis(phenylethynyl)silane 在 naphthalen-1-yl-lithium 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 3,4-diphenyl-1,1-diisopropyl-2,5-dilithiosilole
  参考文献：
  名称：

  Oligosiloles: First Synthesis Based on a Novel Endo-Endo Mode Intramolecular Reductive Cyclization of Diethynylsilanes

  摘要：

  A general and versatile synthesis of 2,5-difunctional siloles and their conversion into oligosiloles are described. Diethynylsilanes undergo intramolecular reductive cyclization in an endo-endo mode upon treatment with lithium naphthalenide to form 2,5-dilithiosiloles. The 2,5-dilithiosiloles ate converted into various 2,5-difunctional siloles by treatment with electrophiles. The resulting 2,5-dibromosilole is further converted into several highly functionalized siloles via palladium-catalyzed cross-coupling reaction or selective mono-lithiation using n-butyllithium in ether. Oligosiloles, from bisiloles to quatersilole, are prepared from certain functional siloles. Oxidative coupling of 2,5-dilithiosilole by use of an Fe(III) complex affords 2,2'-bisilole as yellow crystals. Difunctional oligosiloles, 5,5'-dibromo-2,2'-bisilole and 5,5'''-dibromo-2,2':5',2'':5'',2'''-quatersilole, are prepared by oxidative coupling via higher order cyanocuprate of 2-bromo-5-lithiosilole and 5-bromo-5'-lithio-2,2'-bisilole, respectively. X-ray crystal structures of these bisiloles show highly twisted arrangements between two silole rings with 62-64 degrees of torsion angle. H-1 NMR studies on bisiloles show a rapid equilibration between non-coplanar conformers in solution. In UV-visible spectra, nevertheless, all of the oligosiloles have unusually long absorption maxima.

  DOI：

  10.1021/ja00105a012

文献信息

• Tamao Kohei, Yamaguchi Shigehiro, Shiro Motoo, J. Amer. Chem. Soc, 116 (1994) N 26, S 11715-11722
  作者：Tamao Kohei, Yamaguchi Shigehiro, Shiro Motoo

  DOI：——

  日期：——