N-(cinnamylideneamino)-4-methylaniline | 88254-47-1

• 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: N-(cinnamylideneamino)-4-methylaniline
• CAS: 88254-47-1
• 化学式: C₁₆H₁₆N₂
• 分子量: 236.316
• InChiKey: VCXFZLBMXSADBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(cinnamylideneamino)-4-methylaniline 在 aluminum (III) chloride 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以80%的产率得到4-benzyl-6-methylcinnoline
  参考文献：
  名称：

  Aluminium Chloride–Catalyzed Synthesis of 4-Benzyl Cinnolines from Aryl Hydrazones

  摘要：

  An efficient synthesis of 4-benzyl cinnolines from aryl phenylallylidene hydrazone is described. In this report aluminium chloride as a Lewis acid catalyst and toluene as a solvent are used for the synthesis. This method is expected to more advantageous than the other reported methods of synthesis of the cinnoline rings because of its low cost, better yield, and benign reaction conditions.[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2013.853799
• 作为产物：
  描述：

  4-甲基苯肼盐酸盐 、 肉桂醛 以 乙醇 为溶剂， 以58%的产率得到N-(cinnamylideneamino)-4-methylaniline
  参考文献：
  名称：

  I 2介导的氧化性C–N键形成，用于无金属一锅法从α，β-不饱和醛/酮和肼生成二，三和四取代的吡唑

  摘要：

  I 2介导的无金属氧化C–N键形成方法已建立用于区域选择性吡唑合成。这种实用且环保的一锅操作方案无需分离不稳定程度较高的中间体s，并易于从容易获得的多种二，三和四取代（芳基，烷基和/或乙烯基）吡唑中分离α，β-不饱和醛/酮和肼盐。

  DOI：

  10.1021/jo501844x

文献信息

• I₂-Mediated Oxidative C–N Bond Formation for Metal-Free One-Pot Synthesis of Di-, Tri-, and Tetrasubstituted Pyrazoles from α,β-Unsaturated Aldehydes/Ketones and Hydrazines
  作者：Xinting Zhang、Jinfeng Kang、Pengfei Niu、Jie Wu、Wenquan Yu、Junbiao Chang

  DOI：10.1021/jo501844x

  日期：2014.11.7

  An I2-mediated metal-free oxidative C–N bond formation methodology has been established for the regioselective pyrazole synthesis. This practical and eco-friendly one-pot protocol requires no isolation of the less stable intermediates hydrazones and provides a facile access to a variety of di-, tri-, and tetrasubstituted (aryl, alkyl, and/or vinyl) pyrazoles from readily available α,β-unsaturated aldehydes/ketones

  I 2介导的无金属氧化C–N键形成方法已建立用于区域选择性吡唑合成。这种实用且环保的一锅操作方案无需分离不稳定程度较高的中间体s，并易于从容易获得的多种二，三和四取代（芳基，烷基和/或乙烯基）吡唑中分离α，β-不饱和醛/酮和肼盐。
• Aluminium Chloride–Catalyzed Synthesis of 4-Benzyl Cinnolines from Aryl Hydrazones
  作者：Prasanta Gogoi、Sandhya Rani Gogoi、Namita Devi、Pranjit Barman

  DOI：10.1080/00397911.2013.853799

  日期：2014.4.18

  An efficient synthesis of 4-benzyl cinnolines from aryl phenylallylidene hydrazone is described. In this report aluminium chloride as a Lewis acid catalyst and toluene as a solvent are used for the synthesis. This method is expected to more advantageous than the other reported methods of synthesis of the cinnoline rings because of its low cost, better yield, and benign reaction conditions.[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]