2-cyclohexylquinoline-4-carbaldehyde | 913649-20-4

• 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
• 英文名称: 2-cyclohexylquinoline-4-carbaldehyde
• CAS: 913649-20-4
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: LYCURCVXIZQQGW-UHFFFAOYSA-N

物化性质

• 沸点：
  409.5±33.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 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：
  0.38
• 拓扑面积：
  29.96
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-cyclohexylquinoline-4-carbaldehyde 、 乙酰肼 以 乙醇 为溶剂， 反应 8.0h， 以65%的产率得到N-[(Z)-(2-cyclohexyl-4-quinolyl)methyleneamino]acetamide
  参考文献：
  名称：

  Synthesis, anti-tuberculosis activity, and 3D-QSAR study of ring-substituted-2/4-quinolinecarbaldehyde derivatives

  摘要：

  We have previously identified ring-substituted quinolines as a new structural class of anti-tuberculosis agents. In our ongoing efforts at structural optimization of this class, four series of ring-substituted-2/4-quinolinecarbaldehyde derivatives were synthesized. All twenty-four compounds were synthesized using short and convenient one to two high yielding steps. The newly synthesized compounds were tested in vitro against drug-sensitive Mycobacterium tuberculosis H37Hv strain. Several derivatives were found to be promising inhibitors of M. tuberculosis. For example, derivatives 4a-c (Series 2), 7a-d (Series 3), and 8a-b (Series 4) displayed > 90% inhibition at 6.25 mu g/mL in the primary assay. The most active compounds, N-(2-fluorophenyl)-N'-quinolin-2-ylmethylene-hydrazine (4a), N-(2-adamantan-1-yl-quinolin-4-ylmethylene)-N'-(4-fluorophenyl)hydrazine (7c), and N-(2-cyclohexylquinolin-4-ylmethylene)-N'-(2-fluorophenyl)hydrazine (8a), exhibited 99% inhibition at the lowest tested concentration of 3.125 mu g/mL against drug-sensitive M. tuberculosis H37Rv strain. The similarity index based on steric and electrostatic features of the molecules was used, in conjunction with principal component analysis and linear discriminant analysis, successively to classify the molecules based on their activity into two classes. This classification method gives us confidence in predicting the activity class of any new unsynthesized molecule belonging to these series. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.06.049
• 作为产物：
  描述：

  4-喹啉甲醛 、 环己烯 在 Iron(III) nitrate nonahydrate 、 sodium tetrahydroborate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 0.5h， 以72%的产率得到2-cyclohexylquinoline-4-carbaldehyde
  参考文献：
  名称：

  Fe（III）/ NaBH 4促进烯烃的自由基氢杂芳基化

  摘要：

  自由基介导的简单烯烃分子间杂杂芳基化反应得到了发展。通过简单地将杂芳烃，烯烃，Fe（III）和NaBH 4在0°C混合在一起，可以在1 h内以中等到极好的收率提供各种烷基化的杂芳烃。

  DOI：

  10.1021/acs.orglett.7b03313