p-nitrobenzyl acetohydroxamate | 100704-42-5

• 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: p-nitrobenzyl acetohydroxamate
• 英文别名: N-Acetyl-O-(4-nitro-benzyl)-hydroxylamin；N-[(4-nitrophenyl)methoxy]acetamide
• CAS: 100704-42-5
• 化学式: C₉H₁₀N₂O₄
• 分子量: 210.189
• InChiKey: VZLLVXQHICDWGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  p-nitrobenzyl acetohydroxamate 在 lead(IV) acetate 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 N,N'-diacetyl-N,N'-di-(p-nitrobenzyloxy)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
• 作为产物：
  描述：

  potassium acetohydroxamate 、 对硝基溴化苄 在 sodium carbonate 作用下， 以 甲醇 、 水 为溶剂， 以63%的产率得到p-nitrobenzyl acetohydroxamate
  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

• Preparation of Some Alkyl-Substituted Monohydroxamic Acids, N-Acyl-O-alkylhydroxylamines. I
  作者：JAMES H. COOLEY、WILLIAM D. BILLS、JAMES R. THROCKMORTON

  DOI：10.1021/jo01080a014

  日期：1960.10
• Preparation and reactions of N,N'-diacyl-N,N'-dialkoxyhydrazines
  作者：James H. Cooley、Melvyn W. Mosher、Mazhar A. Khan

  DOI：10.1021/ja01009a032

  日期：1968.3
• The Homolytic and Heterolytic Decomposition of N-Nitroso-N-acyl-O-alkylhydroxylamines^1,2
  作者：James H. Cooley、Paul T. Jacobs、Mazhar A. Khan、Leslie Heasley、W. Daniel Goodman

  DOI：10.1021/jo01020a042

  日期：1965.9
• HERON rearrangement of N,N?-diacyl-N,N?-dialkoxyhydrazines ? a theoretical and experimental study
  作者：Stephen A. Glover、Guoning Mo、Arvi Rauk

  DOI：10.1016/s0040-4020(98)01151-x

  日期：1999.3

  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.