2-(4-Bromphenyl)-5-phenyloxadiazinon | 152332-38-2

• 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-(4-Bromphenyl)-5-phenyloxadiazinon
• 英文别名: 2-(4-Bromphenyl)-5-phenyl-6H-1,3,4-oxadiazin-6-on；2-(4-Bromophenyl)-5-phenyl-1,3,4-oxadiazin-6-one
• CAS: 152332-38-2
• 化学式: C₁₅H₉BrN₂O₂
• 分子量: 329.153
• InChiKey: VDPNDURVKOIGGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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-(4-Bromphenyl)-5-phenyloxadiazinon 在 cesium fluoride 作用下， 以 乙腈 为溶剂， 反应 26.0h， 生成 9-(4-Bromophenyl)-10-phenyl-1,2,3,4-tetrahydroanthracene
  参考文献：
  名称：

  应变炔烃和恶二嗪酮的环加成级联反应

  摘要：

  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。

  DOI：

  10.1002/anie.202105244
• 作为产物：
  描述：

  对溴苯甲酰肼 在 盐酸 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 26.0h， 生成 2-(4-Bromphenyl)-5-phenyloxadiazinon
  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

• Cyclic Alkyne Approach to Heteroatom‐Containing Polycyclic Aromatic Hydrocarbon Scaffolds
  作者：Evan R. Darzi、Joyann S. Barber、Neil K. Garg

  DOI：10.1002/anie.201903060

  日期：2019.7.8

  strategy for accessing heteroatom‐containing polycyclic aromatic hydrocarbons (PAHs). Our approach relies on the controlled generation of transient heterocyclic alkynes and arynes. The strained intermediates undergo in situ trapping with readily accessible oxadiazinones. Four sequential pericyclic reactions occur, namely two Diels–Alder/retro‐Diels–Alder sequences, which can be performed in a stepwise

  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。
• [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。
• Indenopyrans – synthesis and photoluminescence properties
  作者：Andreea Petronela Diac、Ana-Maria Ţepeş、Albert Soran、Ion Grosu、Anamaria Terec、Jean Roncali、Elena Bogdan

  DOI：10.3762/bjoc.12.81

  日期：——

  New indeno[1,2-c]pyran-3-ones bearing different substituents at the pyran moiety were synthesized and their photophysical properties were investigated. In solution all compounds were found to be blue emitters and the trans isomers exhibited significantly higher fluorescence quantum yields (relative to 9,10-diphenylanthracene) as compared to the corresponding cis isomers. The solid-state fluorescence spectra revealed an important red shift of λ_max due to intermolecular interactions in the lattice, along with an emission-band broadening, as compared to the solution fluorescence spectra.

  合成了带有吡喃基不同取代基的新型吲哚[1,2-c]吡喃-3-酮，研究了它们的光物理性质。在溶液中，所有化合物均为蓝色发光体，而trans异构体相对于相应的cis异构体表现出显著更高的荧光量子产率（相对于9,10-二苯基蒽）。固态荧光光谱显示，由于晶格间的相互作用，λ_max发生了重要的红移，同时与溶液荧光光谱相比，发射光带宽变宽。
• 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.
• Christl, Manfred; Bodenschatz, Gabriele; Feineis, Erich, Liebigs Annalen, 1996, # 5, p. 853 - 861
  作者：Christl, Manfred、Bodenschatz, Gabriele、Feineis, Erich、Hegmann, Joachim、Huettner, Gerhard、Mertelmeyer, Stefan、Schaetzlein, Klaus

  DOI：——

  日期：——