8-异氰基喹啉 | 3101-17-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 8-异氰基喹啉
• 英文名称: 8-isocyanoquinoline
• CAS: 3101-17-5
• 化学式: C₁₀H₆N₂
• mdl: MFCD06245281
• 分子量: 154.171
• InChiKey: NTWBPKGWDVJVTD-UHFFFAOYSA-N

物化性质

• 熔点：
  69-70 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲醇 、 8-异氰基喹啉 以 二氯甲烷 为溶剂， 反应 4.0h， 以52%的产率得到4-methoxy-4H-imidazo[4,5,1-ij]quinolone
  参考文献：
  名称：

  Applications of C–H Functionalization Logic to Cyclobutane Synthesis

  摘要：

  The application of C-H functionalization logic to target-oriented synthesis provides an exciting new venue for the development of new and useful strategies in organic chemistry. In this article, C-H functionalization reactions are explored as an alternative approach to access pseudodimeric cyclobutane natural products, such as the dictazole and the piperarborenine families. The use of these strategies in a variety of complex settings highlights the subtle geometric, steric, and electronic effects at play in the auxiliary guided C-H fimctionalization of cyclobutanes.

  DOI：

  10.1021/jo4027148
• 作为产物：
  描述：

  光气 、 N-(喹啉-8-基)甲酰胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以64%的产率得到8-异氰基喹啉
  参考文献：
  名称：

  Applications of C–H Functionalization Logic to Cyclobutane Synthesis

  摘要：

  The application of C-H functionalization logic to target-oriented synthesis provides an exciting new venue for the development of new and useful strategies in organic chemistry. In this article, C-H functionalization reactions are explored as an alternative approach to access pseudodimeric cyclobutane natural products, such as the dictazole and the piperarborenine families. The use of these strategies in a variety of complex settings highlights the subtle geometric, steric, and electronic effects at play in the auxiliary guided C-H fimctionalization of cyclobutanes.

  DOI：

  10.1021/jo4027148

文献信息

• Silver-Catalyzed Chemoselective [4+2] Annulation of Two Isocyanides: A General Route to Pyridone-Fused Carbo- and Heterocycles
  作者：Zhongyan Hu、Jinhuan Dong、Yang Men、Zhichen Lin、Jinxiong Cai、Xianxiu Xu

  DOI：10.1002/anie.201611024

  日期：2017.2.6

  silver‐catalyzed chemoselective [4+2] annulation of aryl and heteroaryl isocyanides with α‐substituted isocyanoacetamides was developed for the facile and efficient synthesis of 2‐aminoquinolones, naphthyridines, and phenanthrolines. A mechanism for this multistep domino reaction is proposed on the basis of a 13C‐labeling experiment, according to which an unprecedented chemoselective heterodimerization

  开发了一种银催化的芳基和杂芳基异氰化物与α-取代异氰基乙酰胺的化学选择性[4 + 2]环合反应，可轻松高效地合成2-氨基喹诺酮，萘啶和菲咯啉。在13 C标记实验的基础上，提出了这种多步多米诺反应的机制，根据该机制，两种不同的异氰酸酯空前的化学选择性异二聚生成了α-氨基酮亚胺中间体，该中间体经历1,3-氨基迁移形成α -亚氨基酮基烯酮，然后进行6π电环化。