2-(4-methoxyphenyl)-5-phenyl-6H-1,3,4-oxadiazin-6-one | 86533-97-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-methoxyphenyl)-5-phenyl-6H-1,3,4-oxadiazin-6-one
• 英文别名: 2-(4-Methoxyphenyl)-5-phenyl-1,3,4-oxadiazin-6-one
• CAS: 86533-97-3
• 化学式: C₁₆H₁₂N₂O₃
• 分子量: 280.283
• InChiKey: BLJUSHYJRCHSQU-UHFFFAOYSA-N

物化性质

• 熔点：
  174-176 °C
• 沸点：
  408.7±47.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  60.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenyl)-5-phenyl-6H-1,3,4-oxadiazin-6-one 反应 3.0h， 生成
  参考文献：
  名称：

  Christl, Manfred, Gazzetta Chimica Italiana, 1986, vol. 116, # 1, p. 1 - 18

  摘要：

  DOI：
• 作为产物：
  描述：

  对甲氧基苯甲酰肼 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 22.5h， 生成 2-(4-methoxyphenyl)-5-phenyl-6H-1,3,4-oxadiazin-6-one
  参考文献：
  名称：

  含杂原子多环芳烃支架的环炔方法。

  摘要：

  我们报告了一种获取含杂原子多环芳烃（PAH）的模块化合成策略。我们的方法依赖于瞬时杂环炔烃和芳炔的受控生成。紧张的中间体用容易获得的恶二嗪酮进行原位捕获。发生四个连续的周环反应，即两个狄尔斯-阿尔德/逆狄尔斯-阿尔德序列，可以以逐步或一锅的方式进行，以组装四个新的碳-碳（CC）键。这些研究强调了如何利用杂环紧张中间体来制备新的有机材料。

  DOI：

  10.1002/anie.201903060

文献信息

• [EN] METHODS FOR THE SYNTHESIS OF HETEROATOM CONTAINING POLYCYCLIC AROMATIC HYDROCARBONS<br/>[FR] PROCÉDÉS DE SYNTHÈSE D'HYDROCARBURES AROMATIQUES POLYCYCLIQUES CONTENANT DES HÉTÉROATOMES
  申请人：UNIV CALIFORNIA

  公开号：WO2020041369A1

  公开（公告）日：2020-02-27

  Methods for the synthesis of polycyclic aromatic hydrocarbons and synthesis platforms for performing such syntheses are provided. Methods and platforms are provided that allow for the synthesis of aza-polycyclic aromatic hydrocarbons by an expedient ring assembly. Methods and platforms allow for a modular approach to synthesis that provide multiple new C-C bonds in sequential pericyclic reactions, thus giving access to compounds with multiple axes of substitution.

  提供了合成多环芳烃的方法和执行这些合成的合成平台。提供了允许通过迅速的环组装合成氮杂多环芳烃的方法和平台。提供了模块化合成方法和平台，通过连续的周环反应提供多个新的C-C键，从而获得具有多个取代轴的化合物。
• Cycloaddition Cascades of Strained Alkynes and Oxadiazinones
  作者：Melissa Ramirez、Evan R. Darzi、Joyann S. Donaldson、Kendall N. Houk、Neil K. Garg

  DOI：10.1002/anie.202105244

  日期：2021.8.9

  alkynes to give polycyclic aromatic hydrocarbons (PAHs). The reaction proceeds by way of a pericyclic reaction cascade and leads to the formation of four new carbon−carbon bonds. Using M06-2X DFT calculations, we interrogate several mechanistic aspects of the reaction, such as why the use of non-aromatic strained alkynes can be used to access unsymmetrical PAHs, whereas the use of arynes in the methodology

  我们报告了恶二嗪酮和应变炔烃反应生成多环芳烃 (PAH) 的计算和实验研究。该反应通过周环反应级联进行，并导致形成四个新的碳-碳键。使用 M06-2X DFT 计算，我们询问了反应的几个机理方面，例如为什么使用非芳族应变炔烃可用于获得不对称 PAH，而在方法中使用芳烃会导致对称 PAH。此外，实验研究能够快速合成新的 PAH，包括并四苯和并五苯支架。这些研究不仅提供了关于上述环加成级联和合成获得 PAH 支架的基本见解，而且还有望实现新材料的合成。
• Modular Synthesis of Unsymmetrical Doubly-ring-fused Benzene Derivatives Based on a Sequential Ring Construction Strategy Using Oxadiazinones as a Platform Molecule
  作者：Tomohiro Meguro、Shengnan Chen、Kazuya Kanemoto、Suguru Yoshida、Takamitsu Hosoya

  DOI：10.1246/cl.190118

  日期：2019.6.5

  An efficient benzene ring construction method using oxadiazinones as a platform molecule has been developed. Sequential reactions of oxadiazinones with cycloalkynes and arynes afforded partially re...

  开发了一种以恶二嗪酮为平台分子的高效苯环构建方法。恶二嗪酮与环炔烃和芳烃的连续反应部分还原...
• Cyclopenta[c]pyrans from 6-oxo-6H-1,3,4-oxadiazines†
  作者：Manfred Christl、Notker Bien、Gabriele Bodenschatz、Erich Feineis、Joachim Hegmann、Carola Hofmann、Stefan Mertelmeyer、Joachim Ostheimer、Frank Sammtleben、Susanne Wehner、Eva-Maria Peters、Karl Peters、Matthias Pfeiffer、Dietmar Stalke

  DOI：10.1039/a807233g

  日期：——

  Prepared in a three-step sequence including acid-catalysed cycloaddition of cyclopentadiene to 6-oxo-6H-1,3,4-oxadiazines, dehydrogenation with DDQ of the dihydro-α-pyrones formed and reduction of the resulting α-pyrones with DIBAL-H, 1,4-disubstituted cyclopenta[c]pyrans are shown to undergo electrophilic substitution; the molecular structures of 1-(4-anisyl)-4-phenylcyclopenta[c]pyran and 4-isopropyl-1-phenylcyclopenta[c]pyran-7-carbaldehyde have been determined by single crystal X-ray diffraction studies.

  通过酸催化环戊二烯与 6-氧代-6H-1,3,4-恶二嗪的环加成反应、用 DDQ 对生成的二氢-δ-吡喃进行脱氢反应以及用 DIBAL-H 对生成的δ-吡喃进行还原反应等三步顺序制备的 1,4-二取代环戊并[c]吡喃发生了亲电取代反应；通过单晶 X 射线衍射研究确定了 1-(4-甲氧基苯基)-4-苯基环戊并[c]吡喃和 4-异丙基-1-苯基环戊并[c]吡喃-7-甲醛的分子结构。
• 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.