苯(甲)醛,4-甲氧基-,O-(2,4-二硝基苯基)肟,(E)- | 115828-58-5

• 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,4-甲氧基-,O-(2,4-二硝基苯基)肟,(E)-
• 英文名称: 4-methoxy-benzaldehyde-[O-(2,4-dinitro-phenyl)-seqtrans-oxime ]
• 英文别名: 4-Methoxy-benzaldehyd-[O-(2,4-dinitro-phenyl)-seqtrans-oxim]；(E)-N-(2,4-dinitrophenoxy)-1-(4-methoxyphenyl)methanimine
• CAS: 115828-58-5
• 化学式: C₁₄H₁₁N₃O₆
• 分子量: 317.258
• InChiKey: ZZANNJUTRHWMOW-OQLLNIDSSA-N

物化性质

• 沸点：
  479.2±55.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  117.1
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  苯(甲)醛,4-甲氧基-,O-(2,4-二硝基苯基)肟,(E)- 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 sodium 2,4-dinitrophenoxide 、 4-甲氧基苯甲腈
  参考文献：
  名称：

  (E)-O-芳基苯甲醛肟与甲醇钠在甲醇中的反应。离去基团对形成腈的过渡态的影响

  摘要：

  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

  DOI：

  10.1021/ja00035a040

文献信息

• Eliminations from (E)-O-Arylbenzaldoximes promoted by tertiary amines in acetonitrile. Effects of aryl substituents, base strength, and leaving group upon the nitrile-forming transition state
  作者：Bong Rae. Cho、Kee Dong. Kim、Jong Chan. Lee、Nam Soon. Cho

  DOI：10.1021/ja00226a032

  日期：1988.8

  Reaction d'elimination des dinitro-2,4 phenyloxime et picryloxime du benzaldehyde. Les resultats observes sont en faveur d'un mecanisme E2

  反应 d'elimination des dinitro-2,4 phenyloxime et picryloxime du benzaldehyde。Les resultats 观察sont en faveur d'un mecanisme E2
• Eliminations from (E)-O-arylbenzaldehyde oximes promoted by hydroxide in 60% aq. Dimethyl sulphoxide. Mechanism and transition-state characteristics of nitrile-forming eliminations
  作者：Bong Rae Cho、Jong Chan Lee、Nam Soon Cho、Kee Dong Kim

  DOI：10.1039/p29890000489

  日期：——

  Reactions of the (E)-O-arylbenzaldehyde oximes (1; Ar = 2,4-dinitrophenyl), (2; Ar =p-nitrophenyl), and (3; Ar = phenyl) with OH– in 60% aq. DMSO have been investigated. The eliminations are quantitative, producing only benzonitriles and aryloxides. The observation of second-order kinetics, k2OD–/k2OH–= 1.15–1.84, and βlg=–0.59 is consistent with an E2 mechanism. The Hammett ρ and k2OD–/k2OH– values

  （的反应ë） - Ö -arylbenzaldehyde肟（1 ; Ar为2,4-二硝基苯基），（2 ; Ar为p硝基苯基），和（3 ; Ar为苯基）与OH -在60％的水溶液。已对DMSO进行了调查。消除是定量的，仅产生苄腈和芳基氧化物。的二级动力学的观察，ķ 2 OD - / ķ 2 OH - = 1.15-1.84，和β LG = -0.59是具有一致的ë 2机构。哈米特ρ和k 2 OD – / k 2OH –离开群体较弱的人会增加价值。对于给定的衬底上的ķ 2 OD - /ķ 2 OH -值保持（实验误差之内）大致恒定，尽管在β芳基取代基的变化。过渡态参数的这些变化可以根据所涉及的形成亚硝酸盐的不同过渡态来解释。
• 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.