N-Triphenylstannyl-pyrrol | 95166-15-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N-Triphenylstannyl-pyrrol
• 英文别名: triphenyltin(IV) pyrrolide；Pyrrol-1-ide;triphenylstannanylium
• CAS: 95166-15-7
• 化学式: C₂₂H₁₉NSn
• 分子量: 416.11
• InChiKey: UTQMIXVRHBOAHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  吡咯 、 三苯基氯化锡 在 n-C₄H₉Li 作用下， 以 正己烷 、 甲苯 为溶剂， 以8.2%的产率得到N-Triphenylstannyl-pyrrol
  参考文献：
  名称：

  Synthesis, characterization and comparison of group 14 pyrrolides and indolides Ph3MX (M=Si, Ge, Sn; X=C4H4N, C8H6N)

  摘要：

  The biologically important heterocycles pyrrole, C4H4N, and indole, C8H6N, ought to be useful as reagents in organic synthesis. Unfortunately, working with them has proved to be difficult because they tend to self-polymerize in solution, especially in the presence of acid catalysts. When the self-polymerization can be controlled, however, the pyrrole and indole units should provide an important route to selective N-metal binding, particularly when these ligands are activated by alkyl-lithium reagents. Using this approach, a general synthesis of the group 14 pyrrolides and indolides, Ph3MX (M = Si, Ge, Sn; X = C4H4N, C8H6N), has been developed and the results are reported here. The compounds are formed as high-melting, white crystalline solids and have been characterized by C-13-, Si-29- and Sn-119-NMR, Raman and electron-impact mass spectroscopy as well as elemental analysis. A single-crystal X-ray study of Ph3Si(C4H4N) has shown that the compound is disordered in the tetragonal lattice, even at low temperature (100 K). (C) 2010 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.07.029

文献信息

• Synthesis, characterization and comparison of group 14 pyrrolides and indolides Ph3MX (M=Si, Ge, Sn; X=C4H4N, C8H6N)
  作者：Joël Poisson、Ivor Wharf、D. Scott Bohle、Mirela M. Barsan、Yuxuan Gu、Ian S. Butler

  DOI：10.1016/j.jorganchem.2010.07.029

  日期：2010.11

  The biologically important heterocycles pyrrole, C4H4N, and indole, C8H6N, ought to be useful as reagents in organic synthesis. Unfortunately, working with them has proved to be difficult because they tend to self-polymerize in solution, especially in the presence of acid catalysts. When the self-polymerization can be controlled, however, the pyrrole and indole units should provide an important route to selective N-metal binding, particularly when these ligands are activated by alkyl-lithium reagents. Using this approach, a general synthesis of the group 14 pyrrolides and indolides, Ph3MX (M = Si, Ge, Sn; X = C4H4N, C8H6N), has been developed and the results are reported here. The compounds are formed as high-melting, white crystalline solids and have been characterized by C-13-, Si-29- and Sn-119-NMR, Raman and electron-impact mass spectroscopy as well as elemental analysis. A single-crystal X-ray study of Ph3Si(C4H4N) has shown that the compound is disordered in the tetragonal lattice, even at low temperature (100 K). (C) 2010 Elsevier B. V. All rights reserved.