3-phenyl-2H-naphtho[2,3-b][1,4]-oxazin-2-one | 109590-61-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-phenyl-2H-naphtho[2,3-b][1,4]-oxazin-2-one
• 英文别名: 3-Phenylbenzo[g][1,4]benzoxazin-2-one
• CAS: 109590-61-6
• 化学式: C₁₈H₁₁NO₂
• 分子量: 273.291
• InChiKey: ZVHBXIPZEKCCAS-UHFFFAOYSA-N

物化性质

• 熔点：
  190 °C
• 沸点：
  474.3±28.0 °C(predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-phenyl-2H-naphtho[2,3-b][1,4]-oxazin-2-one 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以76%的产率得到2-phenylnaphtho[2,3-d]oxazole
  参考文献：
  名称：

  NEW SYNTHESIS OF NAPHTHO- AND BENZOXAZOLES: DECOMPOSITION OF NAPHTHO- AND BENZOXAZINONES WITH KOH

  摘要：

  A method that allows the synthesis of 4 different heterocyclic systems of fused aryl oxazoles, i.e., naphtho[1,2-d], naphtho[2,1-d], naphtho[2,3-d], and benzo[d]oxazoles in reasonable yield is del scribed. This method consists of the decomposition of naphtho- and benzoxazinones with KOH.

  DOI：

  10.1081/scc-100000190
• 作为产物：
  描述：

  苯甲酰甲酸甲酯 、 3-氨基-2-萘酚 以 吡啶 为溶剂， 生成 3-phenyl-2H-naphtho[2,3-b][1,4]-oxazin-2-one
  参考文献：
  名称：

  NEW SYNTHESIS OF NAPHTHO- AND BENZOXAZOLES: DECOMPOSITION OF NAPHTHO- AND BENZOXAZINONES WITH KOH

  摘要：

  A method that allows the synthesis of 4 different heterocyclic systems of fused aryl oxazoles, i.e., naphtho[1,2-d], naphtho[2,1-d], naphtho[2,3-d], and benzo[d]oxazoles in reasonable yield is del scribed. This method consists of the decomposition of naphtho- and benzoxazinones with KOH.

  DOI：

  10.1081/scc-100000190

文献信息

• Highly efficient Ir-catalyzed asymmetric hydrogenation of benzoxazinones and derivatives with a Brønsted acid cocatalyst
  作者：Zhengyu Han、Gang Liu、Rui Wang、Xiu-Qin Dong、Xumu Zhang

  DOI：10.1039/c8sc05797d

  日期：——

  Brønsted acid as the cocatalyst, such as hydrochloric acid, to form a possible single anion-binding interaction with the substrate and catalyst, which greatly contributed to the improvement of reactivity and enantioselectivity. Importantly, a creative and efficient synthetic route was developed to construct the important intermediate for the potential IgE/IgG receptor modulator through our catalytic methodology

  N-甲基化ZhaoPhos L5成功开发了Ir催化的苯并恶嗪酮及其衍生物的高效不对称加氢反应作为配体，它可能会在底物，助催化剂布朗斯台德酸和配体之间显示出具有单一阴离子结合相互作用的新活化方式。这种合成方法提供了一系列手性二氢苯并恶嗪酮及其衍生物，具有优异的结果（> 99％转化率，88–96％的收率，91–> 99％ee，最高可达40 500 TON）。成功的关键是利用强布朗斯台德酸作为助催化剂，例如盐酸，与底物和催化剂形成可能的单一阴离子结合相互作用，这极大地促进了反应性和对映选择性的提高。重要的是，通过我们的催化方法体系，开发了一种创新而有效的合成途径来构建潜在的IgE / IgG受体调节剂的重要中间体。
• Microwave assisted regioselective halogenation of benzo[<i>b</i>][1,4]oxazin-2-ones <i>via</i> sp² C–H functionalization
  作者：Sandeep Kumar、Prince、Mohit Gupta、Ram Sunil Kumar Lalji、Brajendra K. Singh

  DOI：10.1039/d2ra07259a

  日期：——

  We are reporting a palladium catalyzed microwave assisted halogenation of 3-phenyl-2H-benzo[b][1,4]oxazine-2-ones.

  我们报告了一种钯催化微波辅助卤化 3-苯基-2H-苯并[b][1,4]恶嗪-2-酮的方法。
• Construction of benzoheterocycles by the reaction of α-arylglyoxylic acids and <i>ortho</i>-functionalized aniline under mild and minimal conditions
  作者：Hang Gong、Fangyuan Zhou、Changqun Cai

  DOI：10.1039/d3ob01163a

  日期：——

  benzoxazinones, quinoxalinones and benzothiazoles by the reaction of α-arylglyoxylic acids and ortho-functionalized aniline. In this reaction, no other reagents are needed except for reactants and solvents. The reaction was carried out at a mild temperature of 50 °C with only water and/or carbon dioxide as the by-product. Therefore, the reaction has high practical atom economy. In addition, this strategy

  这项工作描述了一种通过α-芳基乙醛酸和邻位官能化苯胺反应合成苯并恶嗪酮、喹喔啉酮和苯并噻唑的环保方法。该反应中除了反应物和溶剂外不需要其他试剂。该反应在50℃的温和温度下进行，仅产生水和/或二氧化碳作为副产物。因此，该反应具有较高的实用原子经济性。此外，该策略可以放大到克级，并且可以大规模合成天然产物头孢孟多A。
• Photophysics and Photochemistry of Naphthoxazinone Derivatives
  作者：Santi Nonell、Lourdes R. Ferreras、Alvaro Cañete、Else Lemp、German Günther、Nancy Pizarro、Antonio L. Zanocco

  DOI：10.1021/jo800039r

  日期：2008.7.1

  The photophysics and photochemistry of a series of naphthoxazinones have been studied using a combination of methods ranging from steady-state and time-resolved spectroscopic techniques to product analysis. The photophysics of naphthoxazinone derivatives is very dependent on the structure: phenanthrene-like compounds exhibit higher fluorescence quantum yield than the less aromatic anthracene-like homologous. The latter, exhibit a substantial degree of charge transfer in the excited singlet state. These compounds are fairly photostable in the absence of additives, yielding a single photoproduct arising from the triplet state. The presence of electron donors such as amines increases the photoconsumption quantum yield and changes the product distribution, the primary photoproduct being a dihydronaphthoxazinone that photoreacts further yielding ultimately an oxazoline derivative.
• Biekert,E. et al., Chemische Berichte, 1961, vol. 94, p. 1664 - 1675
  作者：Biekert,E. et al.

  DOI：——

  日期：——