3-iodo-2-(2-(pent-1-yn-1-yl)phenyl)benzo[b]thiophene | 1609017-51-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 3-iodo-2-(2-(pent-1-yn-1-yl)phenyl)benzo[b]thiophene
• CAS: 1609017-51-7
• 化学式: C₁₉H₁₅IS
• 分子量: 402.299
• InChiKey: WAIRBESEWHNUQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.32
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-iodo-2-(2-(pent-1-yn-1-yl)phenyl)benzo[b]thiophene 在 silver hexafluoroantimonate 、 [AuCl(PPh₃)] 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以80%的产率得到5-iodo-6-propylbenzo[b]naphtho[2,1-d]thiophene
  参考文献：
  名称：

  Transition Metal-Catalyzed Cascade Cyclization of Aryldiynes to Halogenated Benzo[b]naphtho[2,1-d]thiophene Derivatives

  摘要：

  Treatment of 2-(2-(2-(2-substituted ethynyl)phenyl)ethynyl)thioanisoles (1) with 5 mol % of Ph3PAuCl/AgSbF6 and 2 equiv of NIS at refluxing CH2Cl2 gave iodo-substituted benzo[b]naphtho[2,1-d]thiophene (6) in good yields. Chloro- and bromo-substituted benzo [b]naphtho [2,1-d] thiophene derivatives (8 and 9) were also generated by treating compound 1 with 5 mol % of PdX2 and 3 equiv of CuX2 at refluxing THF.

  DOI：

  10.1021/jo500377v
• 作为产物：
  描述：

  trimethyl((2-(methylthio)phenyl)ethynyl)silane 在 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 、 碘 、 正丁胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 36.5h， 生成 3-iodo-2-(2-(pent-1-yn-1-yl)phenyl)benzo[b]thiophene
  参考文献：
  名称：

  Transition Metal-Catalyzed Cascade Cyclization of Aryldiynes to Halogenated Benzo[b]naphtho[2,1-d]thiophene Derivatives

  摘要：

  Treatment of 2-(2-(2-(2-substituted ethynyl)phenyl)ethynyl)thioanisoles (1) with 5 mol % of Ph3PAuCl/AgSbF6 and 2 equiv of NIS at refluxing CH2Cl2 gave iodo-substituted benzo[b]naphtho[2,1-d]thiophene (6) in good yields. Chloro- and bromo-substituted benzo [b]naphtho [2,1-d] thiophene derivatives (8 and 9) were also generated by treating compound 1 with 5 mol % of PdX2 and 3 equiv of CuX2 at refluxing THF.

  DOI：

  10.1021/jo500377v