3-Bromo-2-(triethylsilyl)thiophene | 959399-17-8

• 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: 3-Bromo-2-(triethylsilyl)thiophene
• 英文别名: (3-bromothiophen-2-yl)-triethylsilane
• CAS: 959399-17-8
• 化学式: C₁₀H₁₇BrSSi
• 分子量: 277.3
• InChiKey: SQPKCGNYEHFISR-UHFFFAOYSA-N

物化性质

• 沸点：
  286.1±25.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-Bromo-2-(triethylsilyl)thiophene 、 异丁醛 在 叔丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.5h， 以91%的产率得到2-Methyl-1-(2-triethylsilylthiophen-3-yl)propan-1-ol
  参考文献：
  名称：

  Solvent-Controlled C^sp2→O Silyl Migration:  The “One-Pot” Synthesis of 2,3-Disubsituted Thiophenes

  摘要：

  An effective "one-pot" synthesis of disubstituted thiophene derivatives employing 3-bromo-2-silyl thiophenes has been developed. A solvent-controlled [1,4] C-sp2 -> O silyl migration was involved as the key step in this process.

  DOI：

  10.1021/ol702149c
• 作为产物：
  描述：

  3-溴噻吩 、 三乙基氯硅烷 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以95%的产率得到3-Bromo-2-(triethylsilyl)thiophene
  参考文献：
  名称：

  Solvent-Controlled C^sp2→O Silyl Migration:  The “One-Pot” Synthesis of 2,3-Disubsituted Thiophenes

  摘要：

  An effective "one-pot" synthesis of disubstituted thiophene derivatives employing 3-bromo-2-silyl thiophenes has been developed. A solvent-controlled [1,4] C-sp2 -> O silyl migration was involved as the key step in this process.

  DOI：

  10.1021/ol702149c

文献信息

• Directed metalation and regioselective functionalization of 3-bromofuran and related heterocycles with NaHMDS
  作者：Hang Zhao、John W. Dankwardt、Stefan G. Koenig、Surendra P. Singh

  DOI：10.1016/j.tetlet.2011.10.158

  日期：2012.1

  A mild and regioselective functionalization protocol for 3-bromofuran and analogs has been developed. Selective metalation and functionalization of C2 can be achieved as a result of the directing effect of the adjacent electron-withdrawing bromo group. In addition, the C5 position can also be selectively functionalized by blocking the C2 position via silylation or by simply controlling the reaction temperature. These functionalized compounds bearing a C3 bromo substituent may be further elaborated by utilizing a Suzuki-Miyaura cross-coupling procedure. (C) 2011 Elsevier Ltd. All rights reserved.
• Solvent-Controlled C^sp2→O Silyl Migration:  The “One-Pot” Synthesis of 2,3-Disubsituted Thiophenes
  作者：Nelmi O. Devarie-Baez、Brian J. Shuhler、Hua Wang、Ming Xian

  DOI：10.1021/ol702149c

  日期：2007.10.1

  An effective "one-pot" synthesis of disubstituted thiophene derivatives employing 3-bromo-2-silyl thiophenes has been developed. A solvent-controlled [1,4] C-sp2 -> O silyl migration was involved as the key step in this process.