1-methyl-2-nitro-5,6-dihydrobenzo[b]naphtho[2,1-d]thiophene | 1080649-41-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-methyl-2-nitro-5,6-dihydrobenzo[b]naphtho[2,1-d]thiophene
• 英文别名: 1-Methyl-2-nitro-5,6-dihydronaphtho[1,2-b][1]benzothiole
• CAS: 1080649-41-7
• 化学式: C₁₇H₁₃NO₂S
• 分子量: 295.362
• InChiKey: YVFZKNWNVGMDJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  74.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(2-bromoethyl)benzothiophene 、 2-碘-6-硝基甲苯 在 降冰片烯 、 三(2-呋喃基)膦 、 palladium diacetate 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以42%的产率得到1-methyl-2-nitro-5,6-dihydrobenzo[b]naphtho[2,1-d]thiophene
  参考文献：
  名称：

  A Palladium-Catalyzed Approach to Polycyclic Sulfur Heterocycles

  摘要：

  The synthesis of a variety of polycyclic thiophenes and benzothiophenes is accomplished via a palladium-catalyzed domino ortho-alkylation/direct arylation reaction. An examination of the intramolecular direct arylation of thiophenes suggests that an electrophilic metalation mechanism may be present. This method was further extended to include the synthesis of a (thieno)benzoxepine.

  DOI：

  10.1021/jo8020105

文献信息

• A Palladium-Catalyzed Approach to Polycyclic Sulfur Heterocycles
  作者：Andrew Martins、Mark Lautens

  DOI：10.1021/jo8020105

  日期：2008.11.21

  The synthesis of a variety of polycyclic thiophenes and benzothiophenes is accomplished via a palladium-catalyzed domino ortho-alkylation/direct arylation reaction. An examination of the intramolecular direct arylation of thiophenes suggests that an electrophilic metalation mechanism may be present. This method was further extended to include the synthesis of a (thieno)benzoxepine.