2-(p-methylphenyl)-5-phenyl-3,4-oxadiazin-6-one | 131022-63-4

• 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: 2-(p-methylphenyl)-5-phenyl-3,4-oxadiazin-6-one
• 英文别名: 5-phenyl-2-(4-tolyl)-6H-1,3,4-oxadiazin-6-on；2-(4-Tolyl)-5-phenyloxadiazinon；2-(4-Methylphenyl)-5-phenyl-1,3,4-oxadiazin-6-one
• CAS: 131022-63-4
• 化学式: C₁₆H₁₂N₂O₂
• 分子量: 264.283
• InChiKey: VWOWXMXWUJXILE-UHFFFAOYSA-N

物化性质

• 沸点：
  385.7±35.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  51
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(p-methylphenyl)-5-phenyl-3,4-oxadiazin-6-one 、 1,2-二甲撑环己烷 以 甲苯 为溶剂， 反应 72.0h， 以62%的产率得到1,6,7,8,9,10,11,11a-Octahydro-11a-phenyl-3-(4-tolyl)-<1,3,4>oxadiazino<4,5-b>isochinolin-1-on
  参考文献：
  名称：

  Feineis, Erich; Schwarz, Harmut; Hegmann, Joachim, Chemische Berichte, 1993, vol. 126, # 7, p. 1743 - 1748

  摘要：

  DOI：
• 作为产物：
  描述：

  对甲苯甲酰肼 在 盐酸 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 34.0h， 生成 2-(p-methylphenyl)-5-phenyl-3,4-oxadiazin-6-one
  参考文献：
  名称：

  Feineis, Erich; Schwarz, Harmut; Hegmann, Joachim, Chemische Berichte, 1993, vol. 126, # 7, p. 1743 - 1748

  摘要：

  DOI：

文献信息

• An unusual formation of 1<i>H-s</i>-triazole<i>N</i>-imines from reactions of 1,3,4-oxadiazin-6-ones and nitrilimines
  作者：Nikolaos G. Argyropoulos、Ecaterini Corobili、Ecaterini P. Raptopoulou

  DOI：10.1002/jhet.5570330310

  日期：1996.5

  polysubstituted 1H-S-triazole N-imine derivatives is described from reactions of the readily available 1,3,4-oxadiadin-6-one derivatives and nitrilimines. Besides an hydrazide derivative of phenylglyoxylic acid is also formed. Both adducts were characterised by X-ray crystal structure analysis.

  从容易获得的1,3,4-氧杂二恶英-6-一衍生物和腈亚胺的反应中描述了一种新的，不寻常的获得多取代的1 H-S-三唑N-亚胺衍生物的方法。此外，还形成了苯乙醛酸的酰肼衍生物。通过X射线晶体结构分析表征两种加合物。
• Cycloadditionen von 6H-1,3,4-Oxadiazin-6-onen (4,5-Diaza-?-Pyronen). 14. Nicht katalysierte und durch Trifluoressigs�ure katalysierte Reaktionen von 6H-1,3,4-Oxadiazin-6-onen mit Norbornen
  作者：Manfred Christl、Gabriele Bodenschatz、Erich Feineis、Joachim Hegmann、Gerhard H�ttner、Stefan Mertelmeyer、Klaus Sch�tzlein、Hartmut Schwarz

  DOI：10.1002/prac.199533701140

  日期：——

  In 11 out of 13 non-catalysed reactions of oxadiazinones 1 with norbornene, gamma-oxoketenes 4 were observed and could be isolated in three cases (4b,d,m). Except for 4m, all gamma-oxoketenes isomerised to enollactones of type 5 on thermolysis. However, 4b furnished the cyclobutene derivative 10 as the major product. No gamma-oxoketenes were detected in the reactions of Ik and 11, which gave rise to the formation of 5k and the enollactone 19, respectively. The latter was converted into 51 on treatment with trifluoroacetic acid (TFA). Four oxadiazinones 1 were allowed to react with norbornene in the presence of TFA. Three of them (1a,b,l) afforded mixtures of enollactones of type 5 and their diastereomers 12. Heating of 4 in the presence of norbornene led to the formation of the symmetrical delta-lactones 6. This process was observed to be efficient only where the conversion 4 --> 5 is slow (4b) or inoperative (4m). In five cases, the treatment of the components with boron trifluoride etherate proved to be a useful preparative alternative (6a,d,g,h,m). On treatment of 4a with methanol, the pseudoester 7a was formed, whereas 4b gave mixtures of 7b and the esters 8b and 15. Hydrogen chloride converted 4b into the pseudochloride 14, which furnished pseudoester 7b on methanolysis. Reaction of 4b,m with formic acid gave rise to pseudoanhydrides of type 13. From 4b and TFA a mixture of the enollactones 5b and 12b was obtained. Boron trifluoride etherate transformed 4i to enollactone 12i; analogously, 12m resulted on treatment of 4m with trifluoromethanesulfonic acid.
• Structural characterization of new 2-aryl-5-phenyl-1,3,4-oxadiazin-6-ones and their N-aroylhydrazone precursors
  作者：Mihaela Liliana Ţînţaş、Andreea Petronela Diac、Albert Soran、Anamaria Terec、Ion Grosu、Elena Bogdan

  DOI：10.1016/j.molstruc.2013.11.005

  日期：2014.1

  A series of novel 2,5-disubstituted 1,3,4-oxadiazin-6-ones and their N-aroylhydrazone precursors were synthesized and characterized by NMR and UV-Vis spectroscopy. The electronic properties of 2-aryl-5phenyl-1,3,4-oxadiazin-6-ones are mainly dependent on the 2-aryl substituent and their absorption maxima exhibit a red shift in dichloromethane. Single crystal X-ray diffraction on four acylhydrazones indicated the isolation of isomer with Z configuration of the C=N double bond. Intermolecular interactions through strong H-bonding and C-H...pi contacts serve to link the molecules into a three-dimensional supramolecular network. (C) 2013 Elsevier B.V. All rights reserved.
• Argyropoulos, N. G.; Corobili, E.; Terzis, A., Journal of Heterocyclic Chemistry, 1990, vol. 27, # 5, p. 1425 - 1432
  作者：Argyropoulos, N. G.、Corobili, E.、Terzis, A.、Mentzafos, D.

  DOI：——

  日期：——
• Feineis, Erich; Schwarz, Harmut; Hegmann, Joachim, Chemische Berichte, 1993, vol. 126, # 7, p. 1743 - 1748
  作者：Feineis, Erich、Schwarz, Harmut、Hegmann, Joachim、Christl, Manfred、Peters, Eva-Maria、et al.

  DOI：——

  日期：——