bis[2-(ethoxydimethylsilyl)phenyl]acetylene | 625389-85-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: bis[2-(ethoxydimethylsilyl)phenyl]acetylene
• 英文别名: Ethoxy-[2-[2-[2-[ethoxy(dimethyl)silyl]phenyl]ethynyl]phenyl]-dimethylsilane
• CAS: 625389-85-7
• 化学式: C₂₂H₃₀O₂Si₂
• 分子量: 382.65
• InChiKey: CLYDNWOJZIYVGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  bis[2-(ethoxydimethylsilyl)phenyl]acetylene 以61%的产率得到5,5,10,10-tetramethyl-5,10-disila-5,10-dihydroindeno[2,1-a]indene
  参考文献：
  名称：

  EP1548019

  摘要：

  公开号：
• 作为产物：
  描述：

  双(2-溴苯基)乙炔 在 叔丁基锂 、 氯化铵 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 22.0h， 生成 bis[2-(ethoxydimethylsilyl)phenyl]acetylene
  参考文献：
  名称：

  Bis-Silicon-Bridged Stilbene Homologues Synthesized by New Intramolecular Reductive Double Cyclization

  摘要：

  A homologous series of bis-silicon-bridged stilbenes has been synthesized on the basis of a new intramolecular reductive cyclization of bis(o-silyl)-diphenylacetylene. Thus, the reaction of bis(o-silyl)-diphenylacetylenes with excess lithium naphthalenide undergoes the two-electron reduction at the acetylene moiety to produce a dianion intermediate, which further undergoes a double cyclization in a 5-exo mode to produce the bis-silicon-bridged stilbenes. This methodology can also be applied to the synthesis of tetrakis-silicon-bridged bis(styryl)benzenes. The silicon-bridged pi-conjugated systems thus prepared show intense fluorescence in the visible region. Comparison of a bis-silicon-bridged stilbene with its carbon analogue demonstrates the substantial effects of the silicon-bridges on the electronic structures and thus on the fluorescence properties.

  DOI：

  10.1021/ja038487+

文献信息

• EP1548019
  申请人：——

  公开号：——

  公开（公告）日：——
• Bis-Silicon-Bridged Stilbene Homologues Synthesized by New Intramolecular Reductive Double Cyclization
  作者：Shigehiro Yamaguchi、Caihong Xu、Kohei Tamao

  DOI：10.1021/ja038487+

  日期：2003.11.1

  A homologous series of bis-silicon-bridged stilbenes has been synthesized on the basis of a new intramolecular reductive cyclization of bis(o-silyl)-diphenylacetylene. Thus, the reaction of bis(o-silyl)-diphenylacetylenes with excess lithium naphthalenide undergoes the two-electron reduction at the acetylene moiety to produce a dianion intermediate, which further undergoes a double cyclization in a 5-exo mode to produce the bis-silicon-bridged stilbenes. This methodology can also be applied to the synthesis of tetrakis-silicon-bridged bis(styryl)benzenes. The silicon-bridged pi-conjugated systems thus prepared show intense fluorescence in the visible region. Comparison of a bis-silicon-bridged stilbene with its carbon analogue demonstrates the substantial effects of the silicon-bridges on the electronic structures and thus on the fluorescence properties.