cyclohexyl(2,5-dimethoxyphenyl)amine | 516490-60-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cyclohexyl(2,5-dimethoxyphenyl)amine
• 英文别名: N-cyclohexyl-2,5-dimethoxyaniline
• CAS: 516490-60-1
• 化学式: C₁₄H₂₁NO₂
• mdl: MFCD11143045
• 分子量: 235.326
• InChiKey: JWCPWNULJZOXRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cyclohexyl(2,5-dimethoxyphenyl)amine 在 lithium hydroxide 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Synthesis of Novel Thrombin Inhibitors. Use of Ring-Closing Metathesis Reactions for Synthesis of P2 Cyclopentene- and Cyclohexenedicarboxylic Acid Derivatives

  摘要：

  The thrombin inhibitory tripeptide D-Phe-Pro-Arg has been mimicked using either cyclopentenedicarboxylic derivatives or a cyclohexenedicarboxylic derivative as surrogate for the P2 proline. In the P3 position, tertiary amides were optimized as D-Phe P3 replacements. The P1 arginine was, in all compounds, substituted with the more rigid and biocompatible 4-amino-methylbenzamidine. One of the novel inhibitors was cocrystallized with a-thrombin and subjected to X-ray analysis. From analysis of the X-ray crystal structure, new ligands were designed leading to significantly improved binding affinity, the lead candidate exhibiting an in vitro IC50 of 49 nM.

  DOI：

  10.1021/jm021065a
• 作为产物：
  描述：

  2,5-二甲氧基苯胺 、 苯酚 在 Pd/C 、 sodium formate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以90%的产率得到cyclohexyl(2,5-dimethoxyphenyl)amine
  参考文献：
  名称：

  Palladium-catalyzed reductive coupling of phenols with anilines and amines: efficient conversion of phenolic lignin model monomers and analogues to cyclohexylamines

  摘要：

  一种高效的Pd催化的直接偶联方法，将酚类木质素模型单体和类似物与苯胺偶联，使用甲酸钠作为氢供体，生成环己胺。

  DOI：

  10.1039/c5sc00941c

文献信息

• Palladium-catalyzed reductive coupling of phenols with anilines and amines: efficient conversion of phenolic lignin model monomers and analogues to cyclohexylamines
  作者：Zhengwang Chen、Huiying Zeng、Hang Gong、Haining Wang、Chao-Jun Li

  DOI：10.1039/c5sc00941c

  日期：——

  A highly efficient Pd-catalyzed direct coupling of phenolic lignin model monomers and analogues with anilines to give cyclohexylamines using sodium formate as hydrogen donor is described.

  一种高效的Pd催化的直接偶联方法，将酚类木质素模型单体和类似物与苯胺偶联，使用甲酸钠作为氢供体，生成环己胺。
• Synthesis of Novel Thrombin Inhibitors. Use of Ring-Closing Metathesis Reactions for Synthesis of P2 Cyclopentene- and Cyclohexenedicarboxylic Acid Derivatives
  作者：Fredrik Thorstensson、Ingemar Kvarnström、Djordje Musil、Ingemar Nilsson、Bertil Samuelsson

  DOI：10.1021/jm021065a

  日期：2003.3.1

  The thrombin inhibitory tripeptide D-Phe-Pro-Arg has been mimicked using either cyclopentenedicarboxylic derivatives or a cyclohexenedicarboxylic derivative as surrogate for the P2 proline. In the P3 position, tertiary amides were optimized as D-Phe P3 replacements. The P1 arginine was, in all compounds, substituted with the more rigid and biocompatible 4-amino-methylbenzamidine. One of the novel inhibitors was cocrystallized with a-thrombin and subjected to X-ray analysis. From analysis of the X-ray crystal structure, new ligands were designed leading to significantly improved binding affinity, the lead candidate exhibiting an in vitro IC50 of 49 nM.
• N-Alkylation of amines with phenols over highly active heterogeneous palladium hydride catalysts
  作者：Long Yan、Xin-Xin Liu、Yao Fu

  DOI：10.1039/c6ra22383d

  日期：——

  secondary amines in considerable yield via hydrogenation and amination tandem reaction over Al2O3 supported palladium hydride (PdHx) bi-functional catalyst. Note that this system proceeds efficiently with mild conditions under H2 atmosphere, which was difficult to achieve in previous reports. The catalyst and the mechanism of reaction are both studied. Furthermore, various secondary amines can be formed

  通过在Al 2 O 3负载的氢化钯（PdH x）双功能催化剂上进行氢化和胺化串联反应，苯酚以可观的收率直接转化为仲胺。请注意，该系统在H 2气氛中的温和条件下有效运行，这在以前的报告中很难实现。研究了催化剂和反应机理。此外，在该转化体系下可以高产率形成各种仲胺。