N,N'-diethoxy-N,N'-di-(p-methoxybenzoyl)hydrazine | 223652-39-9

• 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,N'-diethoxy-N,N'-di-(p-methoxybenzoyl)hydrazine
• 英文别名: N,N’-diethoxy-4-methoxy-N’-(4-methoxybenzoyl)benzohydrazide；N,N'-diethoxy-4-methoxy-N'-(4-methoxybenzoyl)benzohydrazide
• CAS: 223652-39-9
• 化学式: C₂₀H₂₄N₂O₆
• 分子量: 388.42
• InChiKey: OGVPHJSKEOINQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  77.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-diethoxy-N,N'-di-(p-methoxybenzoyl)hydrazine 以 均三甲苯 为溶剂， 生成 茴香酸乙酯
  参考文献：
  名称：

  HERON rearrangement of N,N?-diacyl-N,N?-dialkoxyhydrazines ? a theoretical and experimental study

  摘要：

  Ab initio calculations at the B3LYP/6-31G* level on N-methoxy-N-dimethylaminoformamide and its rearrangement to methyl formate and 1,1-dimethyldiazene through the HERON reaction, have been carried out in conjunction with an experimental study of the HERON reactions of N,N'-diacyl-N,N'-dialkoxyhydrazines. Substituent effects are in accord with the theoretical properties of the transition state and point to an anomerically driven process in which donor groups on the anomeric nitrogen and withdrawing groups on the migrating alkoxy oxygen facilitate the rearrangement process. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01151-x
• 作为产物：
  描述：

  potassium p-methoxybenzohydroxamate 在 lead(IV) acetate 、 sodium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 27.5h， 生成 N,N'-diethoxy-N,N'-di-(p-methoxybenzoyl)hydrazine
  参考文献：
  名称：

  HERON rearrangement of N,N?-diacyl-N,N?-dialkoxyhydrazines ? a theoretical and experimental study

  摘要：

  Ab initio calculations at the B3LYP/6-31G* level on N-methoxy-N-dimethylaminoformamide and its rearrangement to methyl formate and 1,1-dimethyldiazene through the HERON reaction, have been carried out in conjunction with an experimental study of the HERON reactions of N,N'-diacyl-N,N'-dialkoxyhydrazines. Substituent effects are in accord with the theoretical properties of the transition state and point to an anomerically driven process in which donor groups on the anomeric nitrogen and withdrawing groups on the migrating alkoxy oxygen facilitate the rearrangement process. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01151-x

文献信息

• Electrodimerization of <i>N</i>-Alkoxyamides for the Synthesis of Hydrazines
  作者：Abudulajiang Nasier、Xihao Chang、Chang Guo

  DOI：10.1021/acs.joc.1c01294

  日期：2021.11.19

  wide range of advanced, highly functionalized hydrazines. Remarkably, an N-centered radical generated from the cleavage of the N–H bond under electrolytic conditions plays a crucial role in this transformation. Furthermore, various N-alkoxyamides bearing different substituents are suitable in this transformation, furnishing the corresponding hydrazines in up to 92% yield.

  据报道，在未分开的电解条件下，N-烷氧基酰胺的有效且有价值的 N-N 二聚反应。这种电化学策略提供了一种强大的方法来获得各种先进的、高度官能化的肼。值得注意的是，电解条件下 N-H 键断裂产生的N中心自由基在这种转变中起着至关重要的作用。此外，带有不同取代基的各种N-烷氧基酰胺适用于这种转化，以高达 92% 的产率提供相应的肼。