N,N-dimethyl-4-((2-(1-phenylethylidene)hydrazono)methyl)aniline | 402945-11-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-dimethyl-4-((2-(1-phenylethylidene)hydrazono)methyl)aniline
• 英文别名: N,N-Dimethyl-4-[(Z)-((E)-1-phenylethylidenehydrazinylidene)methyl]aniline；N,N-dimethyl-4-[(1-phenylethylidenehydrazinylidene)methyl]aniline
• CAS: 402945-11-3
• 化学式: C₁₇H₁₉N₃
• 分子量: 265.358
• InChiKey: TZAMHKUTURYHSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  28
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯乙酮对甲苯磺酰腙 、 对二甲氨基苯甲醛 在 三苯基膦 、 lithium tert-butoxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 14.0h， 以61%的产率得到N,N-dimethyl-4-((2-(1-phenylethylidene)hydrazono)methyl)aniline
  参考文献：
  名称：

  三苯基膦捕获原位生成的重氮化合物或铜类化合物：通过醛与酮衍生的N-甲苯磺酰Reaction的反应选择性合成反式烯烃和不对称叠氮化合物

  摘要：

  AbstractCopper(II) acetylacetonate‐catalyzed Wittig olefination reactions of aldehydes with ketone‐derived N‐tosylhydrazones are reported. A series of tosylhydrazones was investigated and our results showed that the carbon number of the alkyl chain influences the E‐selecivity of the alkenes greatly. Alkenes could be obtained in moderate yields and excellent E‐selectivity when the carbon numbers were up to two. Under metal‐free conditions, triphenylphosphine was able to capture the in situ generated diazo compounds and the corresponding unsymmetrical azines were formed in good yields.magnified image

  DOI：

  10.1002/adsc.201300302

文献信息

• Capture of<i>In Situ</i>Generated Diazo Compounds or Copper Carbenoids by Triphenylphosphine: Selective Synthesis of<i>trans</i>- Alkenes and Unsymmetric Azines<i>via</i>Reaction of Aldehydes with Ketone-Derived<i>N</i>-Tosylhydrazones
  作者：Qiang Sha、Yifei Ling、Wenyong Wang、Yunyang Wei

  DOI：10.1002/adsc.201300302

  日期：2013.8.12

  AbstractCopper(II) acetylacetonate‐catalyzed Wittig olefination reactions of aldehydes with ketone‐derived N‐tosylhydrazones are reported. A series of tosylhydrazones was investigated and our results showed that the carbon number of the alkyl chain influences the E‐selecivity of the alkenes greatly. Alkenes could be obtained in moderate yields and excellent E‐selectivity when the carbon numbers were up to two. Under metal‐free conditions, triphenylphosphine was able to capture the in situ generated diazo compounds and the corresponding unsymmetrical azines were formed in good yields.magnified image