(E)-N'-(1-(4-cyanophenyl)ethylidene)benzohydrazide

• 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: (E)-N'-(1-(4-cyanophenyl)ethylidene)benzohydrazide
• 英文别名: (E)-N’-(1-(4-cyanophenyl)ethylidene)benzohydrazide；N-[(E)-1-(4-cyanophenyl)ethylideneamino]benzamide
• 化学式: C₁₆H₁₃N₃O
• 分子量: 263.299
• InChiKey: AUOSBHAAFOGBEV-LDADJPATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  65.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-[(三甲基硅基)乙炔基]苄腈 在 Ph₃PAuNTf₂ 、 potassium carbonate 作用下， 以 甲醇 、 氯苯 为溶剂， 反应 8.0h， 生成 (E)-N'-(1-(4-cyanophenyl)ethylidene)benzohydrazide
  参考文献：
  名称：

  Gold-Catalyzed Hydrohydrazidation of Terminal Alkynes

  摘要：

  Facile gold-catalyzed hydrohydrazidation of alkynes with various hydrazides (RCONHNH2)-C-2 (R = Alk or Ar; including those with an additional nudeophilic moiety) in the presence of Ph3PAuNTf2 (6 mol %) leading to a wide range of substituted keto-N-acylhydrazones (18 examples) in excellent to good yields (99-66%) is reported. This novel metal-catalyzed coupling proceeds under mild conditions (chlorobenzene, 60 degrees C), exhibits high functional group tolerance, and is insensitive to the electronic and steric effects of the substituents in the reactants.

  DOI：

  10.1021/acs.orglett.8b02019

文献信息

• Recyclable gold(I)-catalyzed hydrohydrazidation of terminal alkynes towards keto-N-acylhydrazones
  作者：Siqi Liu、Jianying Li、Wenli Hu、Bin Huang、Mingzhong Cai

  DOI：10.1016/j.jorganchem.2022.122411

  日期：2022.9

  heterogeneous gold(I)-catalyzed hydrohydrazidation of terminal alkynes with diverse hydrazides has been developed in chlorobenzene at 60 °C by using an MCM-41-immobilized diphenylphosphine gold(I) complex [Ph2P-MCM-41-AuNTf2] as the catalyst, providing a novel and practical method for the synthesis of a wide variety of substituted keto-N-acylhydrazones in good to excellent yields. This heterogenized gold(I) catalyst

  使用 MCM-41 固定的二苯基膦金 (I) 配合物 [Ph 2 P-MCM-41 ，在 60 °C 的氯苯中，开发了一种简便高效的非均相金 (I) 催化的末端炔烃与多种酰肼的加氢反应。-AuNTf 2 ] 作为催化剂，为合成多种取代的酮基-N-酰基腙提供了一种新颖实用的方法，产率从良好到优异。这种异质化的金 (I) 催化剂也很容易通过过滤反应混合物来回收，并且可以回收多达八次，而没有任何明显的催化效率损失。
• Gold-Catalyzed Hydrohydrazidation of Terminal Alkynes
  作者：Dmitry P. Zimin、Dmitry V. Dar’in、Valentin A. Rassadin、Vadim Yu. Kukushkin

  DOI：10.1021/acs.orglett.8b02019

  日期：2018.8.17

  Facile gold-catalyzed hydrohydrazidation of alkynes with various hydrazides (RCONHNH2)-C-2 (R = Alk or Ar; including those with an additional nudeophilic moiety) in the presence of Ph3PAuNTf2 (6 mol %) leading to a wide range of substituted keto-N-acylhydrazones (18 examples) in excellent to good yields (99-66%) is reported. This novel metal-catalyzed coupling proceeds under mild conditions (chlorobenzene, 60 degrees C), exhibits high functional group tolerance, and is insensitive to the electronic and steric effects of the substituents in the reactants.