methyl(2-((2-(p-tolylethynyl)phenyl)ethynyl)phenyl)sulfane | 1367458-45-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: methyl(2-((2-(p-tolylethynyl)phenyl)ethynyl)phenyl)sulfane
• 英文别名: 1-Methyl-4-[2-[2-[2-(2-methylsulfanylphenyl)ethynyl]phenyl]ethynyl]benzene；1-methyl-4-[2-[2-[2-(2-methylsulfanylphenyl)ethynyl]phenyl]ethynyl]benzene
• CAS: 1367458-45-4
• 化学式: C₂₄H₁₈S
• 分子量: 338.473
• InChiKey: IKPKESZNDOXKIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  methyl(2-((2-(p-tolylethynyl)phenyl)ethynyl)phenyl)sulfane 在 N-碘代丁二酰亚胺 、 silver hexafluoroantimonate 、 [AuCl(PPh₃)] 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以80%的产率得到5-iodo-6-(p-tolyl)benzo[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：

  1-乙炔基-2-(甲硫基)苯 在 copper(l) iodide 、 四(三苯基膦)钯 、 正丁胺 作用下， 以 乙醚 为溶剂， 反应 12.0h， 生成 methyl(2-((2-(p-tolylethynyl)phenyl)ethynyl)phenyl)sulfane
  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

• Cascade cyclization of aryldiynes using iodine: synthesis of iodo-substituted benzo[b]naphtho[2,1-d]thiophene derivatives for dye-sensitized solar cells
  作者：Giovanni Ferrara、Tienan Jin、Md. Akhtaruzzaman、Ashraful Islam、Liyuan Han、Hua Jiang、Yoshinori Yamamoto

  DOI：10.1016/j.tetlet.2012.02.007

  日期：2012.4

  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.
• 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.