5-氯-6-喹啉胺 | 778516-03-3

• 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: 5-氯-6-喹啉胺
• 中文别名: 6-喹啉胺,5-氯-
• 英文名称: 5-chloro-[6]quinolylamine
• 英文别名: 5-Chlor-[6]chinolylamin；6-Amino-5-chlorchinolin；5-Chloroquinolin-6-amine
• CAS: 778516-03-3
• 化学式: C₉H₇ClN₂
• 分子量: 178.621
• InChiKey: WTRMRECJKJDLBA-UHFFFAOYSA-N

物化性质

• 沸点：
  337.7±22.0 °C(Predicted)
• 密度：
  1.363±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  5-氯-6-喹啉胺 生成 5-chloro-6-iodo-quinoline
  参考文献：
  名称：

  Howitz; Fraenkel; Schroeder, Justus Liebigs Annalen der Chemie, 1913, vol. 396, p. 63

  摘要：

  DOI：
• 作为产物：
  描述：

  6-氨基喹啉 在 sodium chloride 作用下， 以 二甲基亚砜 为溶剂， 生成 5-氯-6-喹啉胺
  参考文献：
  名称：

  Understanding Flavin-Dependent Halogenase Reactivity via Substrate Activity Profiling

  摘要：

  The activity of four native FDHs and four engineered FDH variants on 93 low-molecular-weight arenes was used to generate FDH substrate activity profiles. These profiles provided insights into how substrate class, functional group substitution, electronic activation, and binding affect FDH activity and selectivity. The enzymes studied could halogenate a far greater range of substrates than have been previously recognized, but significant differences in their substrate specificity and selectivity were observed. Trends between the electronic activation of each site on a substrate and halogenation conversion at that site were established, and these data, combined with docking simulations, suggest that substrate binding can override electronic activation even on compounds differing appreciably from native substrates. These findings provide a useful framework for understanding and exploiting FDH reactivity for organic synthesis.

  DOI：

  10.1021/acscatal.6b02707

文献信息

• Synthesis of mono-substituted derivatives of 6-aminoquinoline
  作者：Tian Lan、Xian Xia Yuan、Jiang Hong Yu、Chao Jia、Yu Shi Wang、Hui Juan Zhang、Zi Feng Ma、Wei Dong Ye

  DOI：10.1016/j.cclet.2010.10.005

  日期：2011.3

  Abstract Several 6-aminoquinoline derivatives, which could be used in drug design, have been synthesized. The reaction conditions were comparatively studied, and the p -chloroaniline was used as optimum oxidant in Skraup–Doebner–Von Miller reaction. The nitro group was reduced effectively by SnCl 2 with no halo-removed occurred.

  摘要合成了几种可用于药物设计的6-氨基喹啉衍生物。对反应条件进行了比较研究，对氯苯胺被用作Skraup–Doebner–Von Miller反应的最佳氧化剂。SnCl 2有效还原了硝基，没有卤素被去除。
• Kern, Dissertation <Freiburg 1906>, S. 7
  作者：Kern

  DOI：——

  日期：——
• Howitz; Fraenkel; Schroeder, Justus Liebigs Annalen der Chemie, 1913, vol. 396, p. 63
  作者：Howitz、Fraenkel、Schroeder

  DOI：——

  日期：——
• Understanding Flavin-Dependent Halogenase Reactivity via Substrate Activity Profiling
  作者：Mary C. Andorfer、Jonathan E. Grob、Christine E. Hajdin、Julia R. Chael、Piro Siuti、Jeremiah Lilly、Kian L. Tan、Jared C. Lewis

  DOI：10.1021/acscatal.6b02707

  日期：2017.3.3

  The activity of four native FDHs and four engineered FDH variants on 93 low-molecular-weight arenes was used to generate FDH substrate activity profiles. These profiles provided insights into how substrate class, functional group substitution, electronic activation, and binding affect FDH activity and selectivity. The enzymes studied could halogenate a far greater range of substrates than have been previously recognized, but significant differences in their substrate specificity and selectivity were observed. Trends between the electronic activation of each site on a substrate and halogenation conversion at that site were established, and these data, combined with docking simulations, suggest that substrate binding can override electronic activation even on compounds differing appreciably from native substrates. These findings provide a useful framework for understanding and exploiting FDH reactivity for organic synthesis.