3-(3-nitrophenyl)-1-benzothiophene | 1415605-86-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(3-nitrophenyl)-1-benzothiophene
• 英文别名: 3-(3-nitrophenyl)benzo[b]thiophene
• CAS: 1415605-86-5
• 化学式: C₁₄H₉NO₂S
• 分子量: 255.297
• InChiKey: HKMJAZGYNZFHCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.14
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3-硝基氯苯 、 苯并噻吩 在 5%-palladium/activated carbon 、 caesium carbonate 、 copper(l) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 96.0h， 以21%的产率得到3-(3-nitrophenyl)-1-benzothiophene
  参考文献：
  名称：

  Completely Regioselective Direct C–H Functionalization of Benzo[b]thiophenes Using a Simple Heterogeneous Catalyst

  摘要：

  The first completely selective C3 C-H arylation of benzo[b]thiophenes is reported, demonstrating previously unexploited reactivity of palladium. Benzo[b]thiophenes are coupled with readily available aryl chlorides using a ligand-free, dual catalytic system of heterogeneous Pd/C and CuCl. The reaction is operationally simple and insensitive to air and moisture, and it provides valuable products with complete selectivity. Significant investigations into the nature of the active catalytic species and mechanistic considerations are discussed.

  DOI：

  10.1021/ja403130g

文献信息

• Pd-Catalyzed β-Selective Direct C–H Bond Arylation of Thiophenes with Aryltrimethylsilanes
  作者：Kenji Funaki、Tetsuo Sato、Shuichi Oi

  DOI：10.1021/ol3029109

  日期：2012.12.21

  Direct arylation of thiophenes and benzothiophenes with aryltrimethylsilanes was effectively catalyzed by PdCl2(MeCN)2 in the presence of CuCl2 as an oxidant. The reaction preferentially occurred at the β-position of both thiophenes and benzothiophenes.

  在CuCl 2作为氧化剂的存在下，PdCl 2（MeCN）2有效地催化了噻吩和苯并噻吩与芳基三甲基硅烷的直接芳基化。该反应优选在噻吩和苯并噻吩的β-位置发生。