2-[(dibenzo[b,d]thiophen-4-yl)sulfanylmethyl]acrylic acid

• 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: 2-[(dibenzo[b,d]thiophen-4-yl)sulfanylmethyl]acrylic acid
• 英文别名: 2-(Dibenzothiophen-4-ylsulfanylmethyl)prop-2-enoic acid；2-(dibenzothiophen-4-ylsulfanylmethyl)prop-2-enoic acid
• 化学式: C₁₆H₁₂O₂S₂
• 分子量: 300.402
• InChiKey: DYBUECMKUSQYDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  90.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(dibenzo[b,d]thiophen-4-yl)sulfanylmethyl]acrylic acid 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以74%的产率得到3,4-dihydro-2H-benzo[b]thieno[3,2-h]thiochromene-3-carboxylic acid
  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 、 2-(溴甲基)丙烯酸 在 正丁基锂 、 sulfur 、 sodium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 0.5h， 以25%的产率得到2-[(dibenzo[b,d]thiophen-4-yl)sulfanylmethyl]acrylic acid
  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

文献信息

• Intramolecular electrophilic hydroarylation via Claisen rearrangement: synthesis of chromenes, heterothiochromenes and heterodihydrothiochromenes
  作者：Rajesh S. Kenny、Uday C. Mashelkar、Deepak M. Rane、Dinesh K. Bezawada

  DOI：10.1016/j.tet.2006.06.079

  日期：2006.9

  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.