3-phenyl-1,2,3,4-oxatriazolium-5-phenylaminide | 55717-75-4

• 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: 3-phenyl-1,2,3,4-oxatriazolium-5-phenylaminide
• 英文别名: N-<3-Phenyl-5-(1,2,3,4-oxatriazolio)>-phenylamid；3-Phenyl-1,2,3,4-oxatriazolium-5-anilid；5-anilino-3-phenyl-[1,2,3,4]oxatriazolium betaine；N,3-diphenyl-1-oxa-2-aza-3-azonia-4-azanidacyclopent-2-en-5-imine
• CAS: 55717-75-4
• 化学式: C₁₃H₁₀N₄O
• 分子量: 238.249
• InChiKey: TWOSIJIJELDTKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-phenyl-1,2,3,4-oxatriazolium-5-phenylaminide 在 硫酸 、 硝酸 作用下， 反应 2.0h， 以64%的产率得到3-phenyl-1,2,3,4-oxatriazolium-5-(2,4-dinitrophenyl)aminide
  参考文献：
  名称：

  氮杂亚砜和氮杂亚胺的硝化：芳基衍生物官能化的方法。

  摘要：

  介电的3-R-1,2,3,4-恶三唑-5-酮和3-取代的1,2,3,4-恶三唑-5-亚胺（分别为氮杂和壬二胺）官能化的第一个例子据报道，亲电反应不会破坏草三唑环。为了开发一种合成相应硝基芳基衍生物的方法，已经评估了使用HNO3 / H2SO4混合物对一系列在邻位，间位和对位带有多个给电子和吸电子取代基的芳基衍生物的硝化作用。硝化发生在氮杂亚砜环的间位，而亲电取代的区域选择性会受到与芳环相连的取代基性质的影响，并且使用这种方法可以很容易地获得各种多官能化衍生物，可能在面向目标的合成中有应用。本文所述的中离子3-取代的1,2,3,4-氧杂三唑衍生物的反应性，合成和结构提供了有关该已知但知之甚少的杂环的有趣的新信息。

  DOI：

  10.1002/cplu.201900243
• 作为产物：
  描述：

  1,4-二苯氨基硫脲 在 盐酸 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 0.25h， 以88%的产率得到3-phenyl-1,2,3,4-oxatriazolium-5-phenylaminide
  参考文献：
  名称：

  Synthesis and multinuclear NMR investigation of some mesoionic 3-phenyl-5-imino-1,2,3,4-oxatriazole imines

  摘要：

  Six new derivatives of mesoionic 3-phenyl-5-imino-1,2,3,4-oxatriazole imine have been obtained and investigated by H-1, C-13, N-14, N-15 and O-17 NMR techniques. The N-15 and O-17 NMR studies reveal that mesoionic oxatriazoles imines exist in a cyclic, 'mesoionic' form. Two stable conformers of mesoionic 3-phenyl-5-imino-1,2,3,4-oxatriazole imines, E and Z, in comparable concentrations, have been detected for the first time in the solution by the use of low temperature NMR experiments. 1H NMR techniques and band shape analysis were applied for estimation of Z-E interconversion barrier of mesoionic 3-phenyl-5-methylimino-1,2,3,4-oxatriazole imine 6 and 3-phenyl-5-benzylimino-1,2,3,4-oxatriazole imine 10. Some one-bond (1)J(N-15-C-13) coupling constants have been measured using N-15 enriched oxatriazole and tetrazole, as a means of the C5-N(-)6 bond characterisation. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2003.08.017

文献信息

• Hanley,R.N. et al., Journal of the Chemical Society. Perkin transactions I, 1979, p. 736 - 740
  作者：Hanley,R.N. et al.

  DOI：——

  日期：——
• HANLEY R. N.; OLLIS W. D.; RAMSDEN C. A., J. CHEM. SOC. PERKIN TRANS., PART 1, 1979, NO 3, 736-740
  作者：HANLEY R. N.、 OLLIS W. D.、 RAMSDEN C. A.

  DOI：——

  日期：——
• Synthesis and multinuclear NMR investigation of some mesoionic 3-phenyl-5-imino-1,2,3,4-oxatriazole imines
  作者：Jarosław Jaźwiński、Olga Staszewska-Krajewska

  DOI：10.1016/j.molstruc.2003.08.017

  日期：2004.1

  Six new derivatives of mesoionic 3-phenyl-5-imino-1,2,3,4-oxatriazole imine have been obtained and investigated by H-1, C-13, N-14, N-15 and O-17 NMR techniques. The N-15 and O-17 NMR studies reveal that mesoionic oxatriazoles imines exist in a cyclic, 'mesoionic' form. Two stable conformers of mesoionic 3-phenyl-5-imino-1,2,3,4-oxatriazole imines, E and Z, in comparable concentrations, have been detected for the first time in the solution by the use of low temperature NMR experiments. 1H NMR techniques and band shape analysis were applied for estimation of Z-E interconversion barrier of mesoionic 3-phenyl-5-methylimino-1,2,3,4-oxatriazole imine 6 and 3-phenyl-5-benzylimino-1,2,3,4-oxatriazole imine 10. Some one-bond (1)J(N-15-C-13) coupling constants have been measured using N-15 enriched oxatriazole and tetrazole, as a means of the C5-N(-)6 bond characterisation. (C) 2003 Elsevier B.V. All rights reserved.
• Nitration of Azasydnones and Azasydnonimines: A Method for the Functionalization of Aryl Derivatives
  作者：Igor L. Dalinger、Olga V. Serushkina、Dmitry L. Lipilin、Aleksei A. Anisimov、Kyrill Yu. Suponitsky、Aleksei B. Sheremetev

  DOI：10.1002/cplu.201900243

  日期：2019.7

  attached to the aryl ring, and a variety of polyfunctionalized derivatives can be readily accessed by using this methodology, which may have applications in the target-oriented synthesis. The reactivity, synthesis, and structure of the mesoionic 3-substituted-1,2,3,4-oxatriazole derivatives described here provide interesting new information on this known but poorly understood heterocycle.

  介电的3-R-1,2,3,4-恶三唑-5-酮和3-取代的1,2,3,4-恶三唑-5-亚胺（分别为氮杂和壬二胺）官能化的第一个例子据报道，亲电反应不会破坏草三唑环。为了开发一种合成相应硝基芳基衍生物的方法，已经评估了使用HNO3 / H2SO4混合物对一系列在邻位，间位和对位带有多个给电子和吸电子取代基的芳基衍生物的硝化作用。硝化发生在氮杂亚砜环的间位，而亲电取代的区域选择性会受到与芳环相连的取代基性质的影响，并且使用这种方法可以很容易地获得各种多官能化衍生物，可能在面向目标的合成中有应用。本文所述的中离子3-取代的1,2,3,4-氧杂三唑衍生物的反应性，合成和结构提供了有关该已知但知之甚少的杂环的有趣的新信息。