反式-8-苯乙烯基喹啉 | 132401-59-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 反式-8-苯乙烯基喹啉
• 英文名称: trans-8-styrylquinoline
• 英文别名: (Z)-8-styrylquinoline；8-[(Z)-2-phenylethenyl]quinoline
• CAS: 132401-59-3
• 化学式: C₁₇H₁₃N
• 分子量: 231.297
• InChiKey: IUULTFPMPWYSHO-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 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：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  反式-8-苯乙烯基喹啉 以 正己烷 为溶剂， 生成 (E)-8-styrylquinoline
  参考文献：
  名称：

  Adiabatic trans-cis photoisomerization and photocyclization of 8-styrylquinoline

  摘要：

  Kinetics of the photocyclization of trans-8-styrylquinoline into 10a, 10b-dihydronaphtho[1,2-h] quinoline (4-azachrysene) was studied in hexane. It was found that in addition to the expected two-step (two-quantum) route with trans-cis photoisomerization occurring in the first step with a quantum yield of phi(tc) = 0.13 with consequent photocyclization of the cis-isomer with a quantum yield of 0.23. The direct single-quantum photocyclization of the trans-isomer with a quantum yield of 0.009 is also observed. The latter observation indicates that the excited trans-isomer isomerizes without loss of excitation to the excited cis-isomer, which then undergoes cyclization, i.e., the trans-cis photoisomerization proceeds partially by adiabatic mechanism t* -> c*. DOI: 10.1134/S0018143910050103

  DOI：

  10.1134/s0018143910050103
• 作为产物：
  描述：

  (E)-8-styrylquinoline 以 正己烷 为溶剂， 生成 反式-8-苯乙烯基喹啉
  参考文献：
  名称：

  Adiabatic trans-cis photoisomerization and photocyclization of 8-styrylquinoline

  摘要：

  Kinetics of the photocyclization of trans-8-styrylquinoline into 10a, 10b-dihydronaphtho[1,2-h] quinoline (4-azachrysene) was studied in hexane. It was found that in addition to the expected two-step (two-quantum) route with trans-cis photoisomerization occurring in the first step with a quantum yield of phi(tc) = 0.13 with consequent photocyclization of the cis-isomer with a quantum yield of 0.23. The direct single-quantum photocyclization of the trans-isomer with a quantum yield of 0.009 is also observed. The latter observation indicates that the excited trans-isomer isomerizes without loss of excitation to the excited cis-isomer, which then undergoes cyclization, i.e., the trans-cis photoisomerization proceeds partially by adiabatic mechanism t* -> c*. DOI: 10.1134/S0018143910050103

  DOI：

  10.1134/s0018143910050103

文献信息

• Preparation of Vinyl Arenes by Nickel-Catalyzed Reductive Coupling of Aryl Halides with Vinyl Bromides
  作者：Jiandong Liu、Qinghua Ren、Xinghua Zhang、Hegui Gong

  DOI：10.1002/anie.201607959

  日期：2016.12.12

  This work emphasizes the synthesis of substituted vinyl arenes by reductive coupling of aryl halides with vinyl bromides under mild and easy‐to‐operate nickel‐catalyzed reaction conditions. A broad range of aryl halides, including heteroaromatics, and vinyl bromides were employed to yielding products in moderate to excellent yields with high functional‐group tolerance. The nickel‐catalytic system displays

  这项工作强调了在温和且易于操作的镍催化反应条件下，通过芳基卤化物与乙烯基溴的还原偶联来合成取代的乙烯基芳烃。广泛使用的芳基卤化物，包括杂芳族化合物和乙烯基溴化物，以中等至优异的收率生产了具有高官能团耐受性的产品。镍催化系统在两个C（sp 2）-卤化物偶合体之间显示出良好的化学选择性，从而证明了不同于其他逐步方案的机理途径。