triisopropyl-(4-thiophen-2-yl-buta-1,3-diynyl)-silane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: triisopropyl-(4-thiophen-2-yl-buta-1,3-diynyl)-silane
• 英文别名: Tri(propan-2-yl)-(4-thiophen-2-ylbuta-1,3-diynyl)silane
• 化学式: C₁₇H₂₄SSi
• 分子量: 288.529
• InChiKey: KHCXWZIUBJLMFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.32
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  triisopropyl-(4-thiophen-2-yl-buta-1,3-diynyl)-silane 在 吡啶 、 copper diacetate 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以82%的产率得到1,8-bis(2-thienyl)-1,3,5,7-octatetrayne
  参考文献：
  名称：

  Synthesis of Diynes and Tetraynes from in Situ Desilylation/Dimerization of Acetylenes

  摘要：

  [GRAPHICS]An efficient method for the in situ desillylation/oxidative dimerization of (trialkylsilyl)acetylenes is described. This protocol avoids the complications encountered with sensitive diynes by eliminating the deprotection and isolation steps. Various aromatic and alkyl diynes and tetraynes can be synthesized in a straightforward manner in good yields (82-99%) from TIPS-protected acetylenes. This method facilitates the efficient synthesis of novel tetrayne-bridged acetylenic cyclophanes 6 and 7 in a direct manner.

  DOI：

  10.1021/ol016414u
• 作为产物：
  描述：

  2-溴噻吩 、 (Z)-(4-chlorobut-3-en-1-ynyl)triisopropylsilane 在 正丁基锂 、 zinc dibromide 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 15.5h， 以86%的产率得到triisopropyl-(4-thiophen-2-yl-buta-1,3-diynyl)-silane
  参考文献：
  名称：

  Synthesis of Diynes and Tetraynes from in Situ Desilylation/Dimerization of Acetylenes

  摘要：

  [GRAPHICS]An efficient method for the in situ desillylation/oxidative dimerization of (trialkylsilyl)acetylenes is described. This protocol avoids the complications encountered with sensitive diynes by eliminating the deprotection and isolation steps. Various aromatic and alkyl diynes and tetraynes can be synthesized in a straightforward manner in good yields (82-99%) from TIPS-protected acetylenes. This method facilitates the efficient synthesis of novel tetrayne-bridged acetylenic cyclophanes 6 and 7 in a direct manner.

  DOI：

  10.1021/ol016414u

文献信息

• Exploiting the dual role of ethynylbenziodoxolones in gold-catalyzed C(sp)–C(sp) cross-coupling reactions
  作者：Somsuvra Banerjee、Nitin T. Patil

  DOI：10.1039/c7cc04283c

  日期：——

  Reported herein is the gold-catalyzed alkynylation of terminal alkynes using ethynylbenziodoxolones (EBXs), where EBXs serve a dual role as oxidants as well as alkyne transfer agents to access unsymmetrical 1,3-diynes. Hence, the catalytic system requires no external oxidants and is compatible with a broad range of substrates, including those with polar functional groups such as NH, OH and B(OH)2.

  本文报道的是使用乙炔基苯并恶恶唑酮（EBX）的末端炔烃的金催化炔基化反应，其中EBX担当氧化剂和炔烃转移剂的双重角色，以访问不对称的1,3-二炔。因此，该催化体系不需要外部氧化剂，并且与各种底物兼容，包括具有极性官能团（例如NH，OH和B（OH）2）的底物。
• Synthesis of Diynes and Tetraynes from in Situ Desilylation/Dimerization of Acetylenes
  作者：Matthew A. Heuft、Shawn K. Collins、Glenn P. A. Yap、Alex G. Fallis

  DOI：10.1021/ol016414u

  日期：2001.9.1

  [GRAPHICS]An efficient method for the in situ desillylation/oxidative dimerization of (trialkylsilyl)acetylenes is described. This protocol avoids the complications encountered with sensitive diynes by eliminating the deprotection and isolation steps. Various aromatic and alkyl diynes and tetraynes can be synthesized in a straightforward manner in good yields (82-99%) from TIPS-protected acetylenes. This method facilitates the efficient synthesis of novel tetrayne-bridged acetylenic cyclophanes 6 and 7 in a direct manner.