2-cyclohexyl-1,2-dihydroquinoline | 123612-53-3

• 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
• 英文名称: 2-cyclohexyl-1,2-dihydroquinoline
• CAS: 123612-53-3
• 化学式: C₁₅H₁₉N
• 分子量: 213.323
• InChiKey: FXSQXDVEVSTLLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  12.03
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-cyclohexyl-1,2-dihydroquinoline 在 sodium 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以42%的产率得到2-cyclohexyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  2-Substituted 1,2,3,4-Tetrahydroquinolines from Quinoline

  摘要：

  将各种有机金属试剂添加到喹啉中，仅发生在杂环芳香环的2位。由此得到的2-取代的1,2-二氢喹啉随后可在乙醇中用钠轻松还原为1,2,3,4-四氢喹啉。喹啉转化为2-取代的1,2,3,4-四氢喹啉的总体过程，相较于之前文献条件（需要中间的氧化步骤），被发现更为有利。最后一步的产率范围为42-98%，但通常大于80%。

  DOI：

  10.1055/s-1989-27209
• 作为产物：
  描述：

  喹啉 、 cyclohexyllithium 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 2-cyclohexyl-1,2-dihydroquinoline
  参考文献：
  名称：

  2-Substituted 1,2,3,4-Tetrahydroquinolines from Quinoline

  摘要：

  将各种有机金属试剂添加到喹啉中，仅发生在杂环芳香环的2位。由此得到的2-取代的1,2-二氢喹啉随后可在乙醇中用钠轻松还原为1,2,3,4-四氢喹啉。喹啉转化为2-取代的1,2,3,4-四氢喹啉的总体过程，相较于之前文献条件（需要中间的氧化步骤），被发现更为有利。最后一步的产率范围为42-98%，但通常大于80%。

  DOI：

  10.1055/s-1989-27209

文献信息

• Synthesis, Structure-Activity Relationships, and Pharmacological Evaluation of Pyrrolo[3,2,1-ij]quinoline Derivatives: Potent Histamine and Platelet Activating Factor Antagonism and 5-Lipoxygenase Inhibitory Properties. Potential Therapeutic Application in Asthma
  作者：Dominique Paris、Michel Cottin、Patrice Demonchaux、Guy Augert、Pierre Dupassieux、Patrick Lenoir、Michael J. Peck、Daniel Jasserand

  DOI：10.1021/jm00004a013

  日期：1995.2

  A series of pyrrolo[3,2,1-ij]quinoline derivatives was synthesized and evaluated for their in vitro and in vivo activities against histamine, platelet activating factor (PAF), and leukotrienes which are recognized to be of importance in asthma. The structure-activity relationship studies have shown that the optimum moiety on the 1-position of the pyrroloquinoline nucleus is a 2-[4-(4-methyl-2-pyridinyl)-1-piperazinyl]ethyl chain in conjunction with a methyl group on the 2-position for potent antagonism of both histamine and PAF. The introduction of substituents on the 8- and 4-positions was also investigated in order to increase the potency of 5-lipoxygenase inhibition while retaining or improving the activities against histamine and PAF. This series is exemplified by 4-n-butyl-5,6-dihydro-8-hydroxy-2-methyl-1-[2-[4-(4-methyl- 2-pyridinyl)-1-piperazinyl]ethyl]-4H-pyrrolo[3,2,1-ij]quinoline (24, KC 11404) which was found to be active against all three of the selected mediators. Compound 24 was found to be orally active in guinea pig models against the histaminic phase of antigen-induced bronchospasm and PAF-induced bronchoconstriction (ED(50) = 1.9 and 2.1 mu mol/kg, respectively). When tested against the leukotriene-dependent phase of the antigen-induced bronchoconstriction, compound 24 showed the same potency as zileuton.
• GOLDSTEIN, STEVEN W.;DAMBEK, PAUL J., SYNTHESIS,(1989) N, C. 221-222
  作者：GOLDSTEIN, STEVEN W.、DAMBEK, PAUL J.

  DOI：——

  日期：——