4-(2-propynylsulfanyl)dibenzo[b,d]thiophene

• 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: 4-(2-propynylsulfanyl)dibenzo[b,d]thiophene
• 英文别名: 4-Prop-2-ynylsulfanyldibenzothiophene；4-prop-2-ynylsulfanyldibenzothiophene
• 化学式: C₁₅H₁₀S₂
• 分子量: 254.376
• InChiKey: FWPBWEPLOWVWLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  53.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-propynylsulfanyl)dibenzo[b,d]thiophene 在 N,N-二乙基苯胺 作用下， 反应 8.0h， 以70%的产率得到2H-benzo[b]thieno[3,2-h]thiochromene
  参考文献：
  名称：

  Intramolecular electrophilic hydroarylation via Claisen rearrangement: synthesis of chromenes, heterothiochromenes and heterodihydrothiochromenes

  摘要：

  We have designed and synthesized several basic and novel fused ring heterocycles by intramolecular hydroarylation with an efficiency and scope to develop intermediates of potential value. This method demonstrated consistent performance with arene-ene and arene-yne substrates of diverse structural features, including propargyl ethers, allyl thioethers, and propargyl thioethers resulting in 6-endo products. (c) 2006 Elsevier Ltd.. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.079
• 作为产物：
  描述：

  二苯并噻吩 、 3-溴丙炔 在 正丁基锂 、 sulfur 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以30%的产率得到4-(2-propynylsulfanyl)dibenzo[b,d]thiophene
  参考文献：
  名称：

  Intramolecular electrophilic hydroarylation via Claisen rearrangement: synthesis of chromenes, heterothiochromenes and heterodihydrothiochromenes

  摘要：

  We have designed and synthesized several basic and novel fused ring heterocycles by intramolecular hydroarylation with an efficiency and scope to develop intermediates of potential value. This method demonstrated consistent performance with arene-ene and arene-yne substrates of diverse structural features, including propargyl ethers, allyl thioethers, and propargyl thioethers resulting in 6-endo products. (c) 2006 Elsevier Ltd.. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.079