5-chloro-6-phenylbenzo[b]naphtho[2,1-d]thiophene | 1609017-61-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-chloro-6-phenylbenzo[b]naphtho[2,1-d]thiophene
• 英文别名: 5-Chloro-6-phenylnaphtho[1,2-b][1]benzothiole；5-chloro-6-phenylnaphtho[1,2-b][1]benzothiole
• CAS: 1609017-61-9
• 化学式: C₂₂H₁₃ClS
• 分子量: 344.864
• InChiKey: PAZMTQDXFOEFSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  methyl(2-((2-(phenylethynyl)phenyl)ethynyl)phenyl)sulfane 在 copper dichloride 、 palladium dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以76%的产率得到5-chloro-6-phenylbenzo[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

文献信息

• Transition Metal-Catalyzed Cascade Cyclization of Aryldiynes to Halogenated Benzo[<i>b</i>]naphtho[2,1-<i>d</i>]thiophene Derivatives
  作者：Chin-Chau Chen、Chu-Mei Chen、Ming-Jung Wu

  DOI：10.1021/jo500377v

  日期：2014.5.16

  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.