2-nitro-4,5-dihydronaphtho[1,2-b]thiophene | 62615-46-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-nitro-4,5-dihydronaphtho[1,2-b]thiophene
• 英文别名: 2-nitro-4,5-dihydro-naphtho[1,2-b]thiophene；4,5-Dihydro-2-nitro-naphtho<1,2-b>thiophen；2-Nitro-4,5-dihydrobenzo[g][1]benzothiole
• CAS: 62615-46-7
• 化学式: C₁₂H₉NO₂S
• 分子量: 231.275
• InChiKey: XWSNOKYPZJHQQE-UHFFFAOYSA-N

物化性质

• 熔点：
  114-116 °C(Solv: ethanol (64-17-5))
• 沸点：
  397.3±30.0 °C(Predicted)
• 密度：
  1.381±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  4-[2-(2-iodophenyl)ethyl]-2-nitrothiophene 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 18.0h， 以32%的产率得到2-nitro-4,5-dihydronaphtho[1,2-b]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 Useful One-Pot Procedure for Obtaining 2-Aryl-5-nitrothiophenes from Bromonitromethane and 3-Aryl-3-chloro-propenals
  作者：Gilbert Kirsch、Juan Rodríguez-Domínguez、David Thomae、Pierre Seck

  DOI：10.1055/s-2007-1000881

  日期：2008.1

  A one-pot procedure was developed to prepare new 2-aryl-5-nitrothiophenes efficiently from bromonitromethane and 3-chloro-3-aryl-propenals. Nitrothiophenes were synthesized in good yields with a simple and easy workup procedure.

  成功开发了一种一步法，以溴硝基甲烷和3-氯-3-芳基丙烯醛为原料高效合成新型2-芳基-5-硝基噻吩。该方法合成硝基噻吩产率高，操作简便，后处理步骤简单。
• 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.