10-methoxy-8-nitro-5,6-dihydro-4H-benzo[6,7]cyclohepta[1,2-b]thiophene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环七噻吩
• 英文名称: 10-methoxy-8-nitro-5,6-dihydro-4H-benzo[6,7]cyclohepta[1,2-b]thiophene
• 英文别名: 14-Methoxy-12-nitro-3-thiatricyclo[8.4.0.02,6]tetradeca-1(10),2(6),4,11,13-pentaene；14-methoxy-12-nitro-3-thiatricyclo[8.4.0.02,6]tetradeca-1(10),2(6),4,11,13-pentaene
• 化学式: C₁₄H₁₃NO₃S
• 分子量: 275.328
• InChiKey: KDNSIURKESMFNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  83.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-碘基-5-硝基苯甲醚 、 3-(3-bromopropyl)thiophene 在 降冰片烯 、 三(2-呋喃基)膦 、 palladium diacetate 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 以52%的产率得到10-methoxy-8-nitro-5,6-dihydro-4H-benzo[6,7]cyclohepta[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

• Synthesis of Polycyclic Heterocycles via a One-Pot Ortho Alkylation/Direct Heteroarylation Sequence
  作者：Andrew Martins、Dino Alberico、Mark Lautens

  DOI：10.1021/ol061859+

  日期：2006.10.1

  Polycyclic thiophenes and furans were synthesized using a one-pot ortho alkylation/direct heteroarylation reaction sequence. Under the optimized reaction conditions, aryl iodides were coupled with 3-(bromoalkyl) thiophenes or -furans, affording six-and seven-membered annulated ring products via formation of two C-C bonds from two aryl C-H bonds.