5-iodo-6-phenylbenzo[b]naphtho[2,1-d]thiophene | 1367458-41-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-iodo-6-phenylbenzo[b]naphtho[2,1-d]thiophene
• 英文别名: 5-Iodo-6-phenylnaphtho[1,2-b][1]benzothiole
• CAS: 1367458-41-0
• 化学式: C₂₂H₁₃IS
• 分子量: 436.316
• InChiKey: UGOKUQMCURZWSV-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

• 作为反应物：
  描述：

  5-iodo-6-phenylbenzo[b]naphtho[2,1-d]thiophene 在 ammonium acetate 、 palladium diacetate 、 potassium carbonate 、 溶剂黄146 、 tricyclohexylphosphine tetrafluoroborate 、 三甲基乙酸 作用下， 以 甲苯 为溶剂， 反应 54.0h， 生成
  参考文献：
  名称：

  Cascade cyclization of aryldiynes using iodine: synthesis of iodo-substituted benzo[b]naphtho[2,1-d]thiophene derivatives for dye-sensitized solar cells

  摘要：

  A facile, efficient, and general synthetic method for iodo-substituted benzo[b]naphtho[2,1-d]thiophenes has been developed via a cascade cyclization of thioanisole-substituted aryldiynes using iodine. A new donor-pi linker-acceptor (D-pi-A) organic dye, G1, with the benzo[b]naphtho[2,1-d]thiophene moiety as an electron donor has been synthesized, and the performance of dye-sensitized solar cell based on G1 has been investigated. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.007
• 作为产物：
  描述：

  3-Iodo-2-[2-(2-phenylethynyl)phenyl]-1-benzothiophene 在 碘 作用下， 以 硝基甲烷 为溶剂， 反应 0.17h， 以96%的产率得到5-iodo-6-phenylbenzo[b]naphtho[2,1-d]thiophene
  参考文献：
  名称：

  Cascade cyclization of aryldiynes using iodine: synthesis of iodo-substituted benzo[b]naphtho[2,1-d]thiophene derivatives for dye-sensitized solar cells

  摘要：

  A facile, efficient, and general synthetic method for iodo-substituted benzo[b]naphtho[2,1-d]thiophenes has been developed via a cascade cyclization of thioanisole-substituted aryldiynes using iodine. A new donor-pi linker-acceptor (D-pi-A) organic dye, G1, with the benzo[b]naphtho[2,1-d]thiophene moiety as an electron donor has been synthesized, and the performance of dye-sensitized solar cell based on G1 has been investigated. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.007

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.