1-bromo-2-(4-trimethylsilyl-1,3-butadiynyl)benzene | 351389-18-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-bromo-2-(4-trimethylsilyl-1,3-butadiynyl)benzene
• 英文别名: 4-(2-Bromophenyl)buta-1,3-diynyl-trimethylsilane
• CAS: 351389-18-9
• 化学式: C₁₃H₁₃BrSi
• 分子量: 277.236
• InChiKey: QFRYEQVCMRGHIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-bromo-2-(4-trimethylsilyl-1,3-butadiynyl)benzene 在 bis-triphenylphosphine-palladium(II) chloride 、 氢氧化钾 、 copper(l) iodide 、 三乙胺 、 碘甲烷 作用下， 以 四氢呋喃 、 水 、 三乙胺 为溶剂， 生成 triisopropyl((2-((2-((2-((triisopropylsilyl)ethynyl)phenyl)buta-1,3-diyn-1-yl)phenyl)hexa-1,3,5-triyn-1-yl)phenyl)ethynyl)silane
  参考文献：
  名称：

  A versatile synthetic route to dehydrobenzoannulenes via in situ generation of reactive alkynes

  摘要：

  This paper outlines the development of a protocol that allows in situ generation of unstable alkynes under Pd-catalyzed cross-coupling conditions. Cu-mediated intramolecular cyclization of the resultant alpha,omega -polyynes provides dehydrobenzoannulenes as singular species, in very good overall yields, and in a variety of topologies that are inaccessible by traditional routes or previously available in low yield only. In addition, we will discuss the solid-state structure and reactivity of these macrocycles, as well as the ability of the planar dehydrobenzoannulenes to support weak induced ring currents. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00229-0
• 作为产物：
  描述：

  邻碘溴苯 、 (Trimethylsilyl)butadiyne 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以93%的产率得到1-bromo-2-(4-trimethylsilyl-1,3-butadiynyl)benzene
  参考文献：
  名称：

  A versatile synthetic route to dehydrobenzoannulenes via in situ generation of reactive alkynes

  摘要：

  This paper outlines the development of a protocol that allows in situ generation of unstable alkynes under Pd-catalyzed cross-coupling conditions. Cu-mediated intramolecular cyclization of the resultant alpha,omega -polyynes provides dehydrobenzoannulenes as singular species, in very good overall yields, and in a variety of topologies that are inaccessible by traditional routes or previously available in low yield only. In addition, we will discuss the solid-state structure and reactivity of these macrocycles, as well as the ability of the planar dehydrobenzoannulenes to support weak induced ring currents. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00229-0