(4-hexyl-5-trimethylsilanyl-thiophen-2-yl)-triethylborate lithium salt

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: (4-hexyl-5-trimethylsilanyl-thiophen-2-yl)-triethylborate lithium salt
• 英文别名: Lithium;triethoxy-(4-hexyl-5-trimethylsilylthiophen-2-yl)boranuide
• 化学式: C₁₉H₃₈BO₃SSi*Li
• 分子量: 392.412
• InChiKey: LTPHKGWFWCRJPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  55.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-溴-3-己基噻吩 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.34h， 生成 (4-hexyl-5-trimethylsilanyl-thiophen-2-yl)-triethylborate lithium salt
  参考文献：
  名称：

  A Novel “Double-Coupling” Strategy for Iterative Oligothiophene Synthesis Using Orthogonal Si/Ge Protection

  摘要：

  [GRAPHICS]A new iterative synthesis of regioregular oligothiophenes has been developed in which "double-coupling" after each iteration minimizes deletion sequences. The method exploits the susceptibility of alpha-silyl- but not alpha-germyl-substituted thiophene derivatives toward nucleophilic ipso-protodemetalation and features an unusual "base-free" Suzuki-type cross-coupling protocol. The strategy has been designed for the solid-phase synthesis of high purity oligothiophenes using a germanium-based linker.

  DOI：

  10.1021/ol025879x

文献信息

• A Novel “Double-Coupling” Strategy for Iterative Oligothiophene Synthesis Using Orthogonal Si/Ge Protection
  作者：Alan C. Spivey、David J. Turner、Michael L. Turner、Stephen Yeates

  DOI：10.1021/ol025879x

  日期：2002.5.1

  [GRAPHICS]A new iterative synthesis of regioregular oligothiophenes has been developed in which "double-coupling" after each iteration minimizes deletion sequences. The method exploits the susceptibility of alpha-silyl- but not alpha-germyl-substituted thiophene derivatives toward nucleophilic ipso-protodemetalation and features an unusual "base-free" Suzuki-type cross-coupling protocol. The strategy has been designed for the solid-phase synthesis of high purity oligothiophenes using a germanium-based linker.