N'-(5-phenyl-1,2,4-oxadiazol-3-yl)-N-(4-nitrophenyl)-formamidine | 31709-24-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N'-(5-phenyl-1,2,4-oxadiazol-3-yl)-N-(4-nitrophenyl)-formamidine
• 英文别名: N-(5-Phenyl-1,2,4-Oxadiazol-3-yl)-N'-p-nitrophenylformamidin；N-(4-nitro-phenyl)-N'-(5-phenyl-[1,2,4]oxadiazol-3-yl)-formamidine；N-(4-nitrophenyl)-N'-(5-phenyl-1,2,4-oxadiazol-3-yl)methanimidamide
• CAS: 31709-24-7；118664-07-6；118688-29-2
• 化学式: C₁₅H₁₁N₅O₃
• 分子量: 309.284
• InChiKey: DKHJUESLXSHTMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N'-(5-phenyl-1,2,4-oxadiazol-3-yl)-N-(4-nitrophenyl)-formamidine 在 三乙胺 作用下， 以 乙腈 为溶剂， 生成 3-Benzoylamino-1-p-nitrophenyl-1,2,4-triazol
  参考文献：
  名称：

  单核杂环重排。侧链结构对反应性的影响。部分3的一些重排ñ - （5-苯基-1,2,4-恶二唑-3-基） - ñ '-arylformamidines成1-芳基-3-苯甲酰基氨基-1,2,4-三唑在乙腈中三乙胺的存在

  摘要：

  表观伪一级速率常数为标题反应得到的曲线绘图与叔胺浓度，根据以下等式ķ甲（ķ ü，+ ķ 1 ķ 2 [TEA]）/（1 + ķ 1 [TEA ]）。这表明发生了两种不同的反应途径。一个独立于[TEA]，另一个独立于[TEA]，这涉及将底物快速转化为酸碱加合物或离子对，然后缓慢转化为相应的三唑。还研究了取代基对这些反应的影响。

  DOI：

  10.1016/s0040-4020(01)85255-8
• 作为产物：
  描述：

  3-氨基-5-苯基-1,2,4-噁二唑 以 四氢呋喃 为溶剂， 生成 N'-(5-phenyl-1,2,4-oxadiazol-3-yl)-N-(4-nitrophenyl)-formamidine
  参考文献：
  名称：

  Ruccia,M. et al., Journal of Heterocyclic Chemistry, 1971, vol. 8, p. 137 - 139

  摘要：

  DOI：

文献信息

• Mononuclear heterocyclic rearrangements. Effect of the structure of the side chain on the reactivity. Part 3. Rearrangement of some N-(5-phenyl-1,2,4-oxadiazol-3-yl)-N′-arylformamidines into 1-aryl-3-benzoylamino-1,2,4-triazoles in acetonitrile in the presence of triethylamine
  作者：Vincenzo Frenna、Gabriella Macaluso、Nicolò Vivona、Domenico Spinelli、Giovanni Consiglio、Elisabetta Mezzina

  DOI：10.1016/s0040-4020(01)85255-8

  日期：1994.1

  The apparent pseudo-first-order rate constants for the title reaction give a curvilinear plot versus tertiary amine concentration, according to the equation kA  (ku, + K1k2[TEA])/(1 + K1[TEA]). This shows the occurrence of two different reaction pathways; the one, independent of [TEA] and the other, dependent on [TEA], which involves a fast conversion of the substrate into an acid-base adduct or an

  表观伪一级速率常数为标题反应得到的曲线绘图与叔胺浓度，根据以下等式ķ甲（ķ ü，+ ķ 1 ķ 2 [TEA]）/（1 + ķ 1 [TEA ]）。这表明发生了两种不同的反应途径。一个独立于[TEA]，另一个独立于[TEA]，这涉及将底物快速转化为酸碱加合物或离子对，然后缓慢转化为相应的三唑。还研究了取代基对这些反应的影响。
• Frenna, Vinzenzo; Vivona, Nicolo; Consiglio, Giovanni, Journal of the Chemical Society. Perkin transactions II, 1993, # 7, p. 1339 - 1343
  作者：Frenna, Vinzenzo、Vivona, Nicolo、Consiglio, Giovanni、Spinelli, Domenico、Mezzina, Elisabetta

  DOI：——

  日期：——
• Ruccia,M. et al., Journal of Heterocyclic Chemistry, 1971, vol. 8, p. 137 - 139
  作者：Ruccia,M. et al.

  DOI：——

  日期：——
• The ionic liquid effect on the Boulton–Katritzky reaction: a comparison between substrates of different structure
  作者：Francesca D'Anna、Daniela Millan、Renato Noto

  DOI：10.1016/j.tet.2015.05.003

  日期：2015.9

  The mononuclear rearrangement of heterocycles, also called Boulton-Katritzky reaction, was studied in ionic liquid solution using N-(5-phenyl-1,2,4-oxadiazol-3-yl)-N'-(4-nitrophenyl)-formamidine as substrate. The investigation was carried out using piperidine as basic catalyst and several ionic liquids differing in both cation and anion structure. Kinetic data collected were compared with the ones previously reported using (Z)-phenylhydrazone of 3-benzoyl-5-phenyl-1,2,4-oxadiazole to have information about the effect due to the different structure of the alkyl chain borne on the substrate. Furthermore, data were analysed on the grounds of polarity, Kamlet-Taft solvent parameters, but taking also in consideration the structural features of the solvent used.On the whole, the results obtained seem to indicate that the 'ionic liquid effect' can be explained considering the structural features of the constituent ions, their effect on the structure of solvent media and their ability to interact with the transition state of the target reaction. (C) 2015 Elsevier Ltd. All rights reserved.