苯(甲)醛,3-溴-,O-(2,4,6-三硝基苯基)肟,(E)- | 115828-62-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苯(甲)醛,3-溴-,O-(2,4,6-三硝基苯基)肟,(E)-
• 英文名称: (E)-1-(3-bromophenyl)-N-(2,4,6-trinitrophenoxy)methanimine
• CAS: 115828-62-1
• 化学式: C₁₃H₇BrN₄O₇
• 分子量: 411.125
• InChiKey: LPNZFNOQDZCZOS-VIZOYTHASA-N

物化性质

• 沸点：
  529.7±60.0 °C(Predicted)
• 密度：
  1.82±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  151.01
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  苯(甲)醛,3-溴-,O-(2,4,6-三硝基苯基)肟,(E)- 在 三乙胺 作用下， 以 乙腈 为溶剂， 生成 间溴苯甲腈 、 2,4,6-三硝基苯酚阴离子
  参考文献：
  名称：

  乙腈中叔胺促进 (E)-O-芳基苯甲醛肟的消除。芳基取代基、碱强度和离去基团对形成腈的过渡态的影响

  摘要：

  反应 d'elimination des dinitro-2,4 phenyloxime et picryloxime du benzaldehyde。Les resultats 观察sont en faveur d'un mecanisme E2

  DOI：

  10.1021/ja00226a032

文献信息

• Reaction of (E)-O-arylbenzaldoximes with sodium methoxide in methanol. Effect of leaving group upon nitrile-forming transition state
  作者：Bong Rae Cho、Jinhee Jung、Eun Kyung Ahn

  DOI：10.1021/ja00035a040

  日期：1992.4

  Reactions of (E)-O-arylbenzaldoximes 1-3 with MeONa-MeOH have been studied kinetically. The reactions proceed via competing E2 and S N Ar reactions, in which the first step is rate-determining. Although the reactions were strongly influenced by the electronic effect of the β- and O-aryl substituents, they were insensitive to the steric effect of the O-aryl group, except that the S N Ar reaction was

  已经对 (E)-O-芳基苯甲醛肟 1-3 与 MeONa-MeOH 的反应进行了动力学研究。反应通过竞争的 E2 和 SN Ar 反应进行，其中第一步是速率确定。尽管反应受到β-和O-芳基取代基的电子效应的强烈影响，但它们对O-芳基的空间效应不敏感，除了SN Ar反应被2的CF 3 基团延迟。对于 MeONa-MeOH 促进的 1-3 消除，k H /k D 值增加，Hammett p 值随着离去基团的改善而降低
• Reactions of (E)-O-arylbenzaldoximes with secondary amines in acetonitrile. Effect of .beta.-aryl substituents upon the competition between E2 and SNAr reactions
  作者：Bong Rae Cho、Jong Tae Je

  DOI：10.1021/jo00075a009

  日期：1993.11

  Reactions of (E)-O-arylbenzaldoximes in which the O-aryl group is 2,4-dinitrophenyl (1a-d) and picryl (2a-d) with secondary amines in acetonitrile have been studied kinetically. The reactions proceeded via competing E2 and S(N)Ar mechanisms. For eliminations from 1a-d promoted by R2NH in MeCN, the transition state was changed toward Elcb-like by a more electron-withdrawing beta-aryl substituent and a stronger base. On the other hand, the transition states for eliminations from 2a-d and for the S(N)Ar reactions of all substrates were relatively insensitive to the variation of either beta-aryl substituent or base strength. The yield of S(N)Ar product increased with base concentration, electron-withdrawing ability of the O-aryl group, and base strength. When the electron-withdrawing ability of the beta-aryl substituent is increased, the yield of S(N)Ar product from 1a-d decreased, although no clear trend was observed for 2a-d. From these results, factors that influence the competition between E2 and S(N)Ar reaction pathways are assessed.