3-phenyl-2H-naphtho[1,2-b][1,4]oxazin-2-one

• 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[1,2-b][1,4]oxazin-2-one
• 英文别名: 3-Phenylbenzo[h][1,4]benzoxazin-2-one
• 化学式: C₁₈H₁₁NO₂
• 分子量: 273.291
• InChiKey: XMJARUXYLHMPHU-UHFFFAOYSA-N

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[1,2-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68%的产率得到2-phenylnaphtho[2,1-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：

  苯乙酮 在 吡啶 、 selenium(IV) oxide 、 1-乙酸基-1,2-苯碘酰-3-(1H)-酮 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 3-phenyl-2H-naphtho[1,2-b][1,4]oxazin-2-one
  参考文献：
  名称：

  高价碘 (III) 促进芳胺与 α-酮酸的自由基氧化 C-H 环化

  摘要：

  开发了一种新的催化剂自由基氧化 C-H 环化芳胺与 α-酮酸在温和条件下合成苯并恶嗪-2-酮的反应。这种高价碘 (III) 促进的过程消除了使用具有高水平官能团耐受性的金属催化剂或添加剂。高价碘 (III) 既是该反应的氧化剂又是自由基引发剂。该方法的合成效用通过天然产物头孢菌素 A 的合成得到证实。

  DOI：

  10.1021/acs.joc.1c01424

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。
• 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.
• Hypervalent Iodine(III)-Promoted Radical Oxidative C–H Annulation of Arylamines with α-Keto Acids
  作者：Lipeng Long、Jieyan Wang、Liuqing Gu、Shiguang Yang、Liang Qiao、Guotian Luo、Zhengwang Chen

  DOI：10.1021/acs.joc.1c01424

  日期：2021.9.3

  acids toward benzoxazin-2-ones synthesis under mild conditions was developed. This hypervalent iodine(III)-promoted process eliminated the use of a metal catalyst or additive with high levels of functional group tolerance. Hypervalent iodine(III) was both an oxidant and a radical initiator for this reaction. The synthetic utility of this method was confirmed by the synthesis of the natural product cephalandole

  开发了一种新的催化剂自由基氧化 C-H 环化芳胺与 α-酮酸在温和条件下合成苯并恶嗪-2-酮的反应。这种高价碘 (III) 促进的过程消除了使用具有高水平官能团耐受性的金属催化剂或添加剂。高价碘 (III) 既是该反应的氧化剂又是自由基引发剂。该方法的合成效用通过天然产物头孢菌素 A 的合成得到证实。
• NEW SYNTHESIS OF NAPHTHO- AND BENZOXAZOLES: DECOMPOSITION OF NAPHTHO- AND BENZOXAZINONES WITH KOH
  作者：Claudio Saitz、Hernán Rodríguez、Amelia Márquez、Alvaro Cañete、Carolina Jullian、Antonio Zanocco

  DOI：10.1081/scc-100000190

  日期：2001.1

  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.