1,2-dihydro-1-(4-fluorophenyl)naphtho[1,2-e][1,3]oxazine-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 1,2-dihydro-1-(4-fluorophenyl)naphtho[1,2-e][1,3]oxazine-3-one
• 英文别名: 1-(4-fluorophenyl)-1,2-dihydro-3H-naphtho[1,2-e][1,3]oxazin-3-one；1-(4-fluorophenyl)-1,2-dihydro-naphtho[1,2-e][1,3]oxazin-3-one；1-(4-Fluorophenyl)-1,2-dihydrobenzo[f][1,3]benzoxazin-3-one
• 化学式: C₁₈H₁₂FNO₂
• 分子量: 293.297
• InChiKey: VUYLQDPRXDCLFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对氟苯甲醛 在 Amberlite IRA-400 Cl anion exchange resin 作用下， 以 neat (no solvent) 为溶剂， 生成 1,2-dihydro-1-(4-fluorophenyl)naphtho[1,2-e][1,3]oxazine-3-one
  参考文献：
  名称：

  以Amberlite IRA-400 Cl树脂为绿色催化剂的一锅多组分合成萘并恶嗪-3-酮衍生物

  摘要：

  一种高效的Amberlite IRA-400 Cl树脂通过以下反应催化无溶剂一锅合成1-芳基-1,2-二氢-3H-萘[1,2-e] [1,3]恶嗪-3-酮描述了芳基醛，脲和β-萘酚的三组分反应。该方法具有诸如后处理容易，对环境的影响小，反应时间短和产率高的优点。回收的催化剂可重复使用四次，而催化活性没有明显损失。

  DOI：

  10.2174/1570178614666170811151040

文献信息

• Lewis Acid Catalyzed Synthesis of 1-Aryl-1,2-dihydro-naphtho[1,2-e][1,3]oxazin-3-ones under Solvent Free Conditions: A Mechanistic Approach
  作者：Mukul Sharma、Sunny Manohar、Diwan S. Rawat

  DOI：10.1002/jhet.825

  日期：2012.5

  Lewis acids catalyzed highly efficient one‐pot three component coupling of β‐naphthol, benzaldehydes and urea to produce 1‐aryl‐1,2‐dihydro‐naphtho[1,2‐e][1,3]oxazin‐3‐one derivatives under solvent free conditions is described. Mechanistic studies confirmed that product formation is possible only at very high temperature (140–150°C) and at lower temperature (90–100°C) formation of 14‐aryl‐14H‐dibenzo(a

  路易斯酸催化β-萘酚，苯甲醛和尿素的高效一锅三组分偶联，生成1-芳基-1,2-二氢萘并[1,2-e] [1,3]恶嗪-3-酮衍生物描述了在无溶剂条件下。机理的研究证实，产物形成可以仅在非常高的温度（140-150℃），并在较低的温度下（90-100℃）的14 -芳基- 14形成ħ -二苯并（A，j）的观察到的呫吨。在筛选的九种路易斯酸中，碘，P 2 O 5和Yb（OTf）3被发现是该多组分反应最有效的催化剂。
• Bi-SO3H-functionalized room temperature ionic liquids based on bipyridinium: highly efficient and recyclable catalysts for the synthesis of naphthalene-condensed oxazinone derivatives
  作者：Yuanyuan Wang、Junlong Zhou、Kun Liu、Liyi Dai

  DOI：10.1039/c3ra00133d

  日期：——

  are the key features of this methodology. Hammett function values and the minimum-energy geometries of bi-SO3H-functionalized ionic liquids were calculated and the results revealed that the acidities and catalytic activities of ionic liquids in the synthesis of naphthalene-condensed oxazinone derivatives were influenced by their structures. There are strong hydrogen bond networks in these bi-SO3H-functionalized

  合成了几种双-SO 3 H-官能化的室温离子液体，并在理论上和实验上研究了它们对合成萘缩合恶嗪酮衍生物的催化性能。与传统的单-SO 3 H-官能化离子液体相比，该方法的主要特点是催化剂用量少，产率高。计算了双SO 3 H-官能化离子液体的哈米特函数值和最小能几何结构，结果表明，离子液体在萘缩合恶嗪酮衍生物的合成中的酸度和催化活性受其结构的影响。这些bi-SO 3中有很强的氢键网络H-官能化离子液体。与分离的阳离子相比，磺酸基团的H–O键延长了不同的水平。H–O键距离最短的离子液体[（PS）2 bPy] [OTf] 2具有最强的氢键，因此显示出最强的酸度和最高的催化活性。
• Synthesis of naphthoxazinone derivatives using silica-bonded S-sulfonic acid as catalyst under solvent-free conditions
  作者：KHODABAKHSH NIKNAm、PARISA ABOLPOUR

  DOI：10.1007/s12039-015-0895-x

  日期：2015.7

  Silica-bonded S-sulfonic acid is employed as a recyclable catalyst for the synthesis of naphthoxazinone derivatives from the reaction of ß-naphthol, aromatic aldehydes and urea at 150°C under solvent-free conditions. The heterogeneous catalyst was recycled for five runs after the reaction of ß-naphthol, benzaldehyde and urea without losing its catalytic activity. Silica-bonded S-sulfonic acid was employed

  二氧化硅键合的S-磺酸用作可循环利用的催化剂，用于在150 ° C无溶剂条件下由β-萘酚，芳族醛和尿素反应合成萘并恶嗪酮衍生物。ß-萘酚，苯甲醛和尿素反应后，将多相催化剂循环使用五次，而不会失去其催化活性。 二氧化硅键合的S-磺酸用作固体酸催化剂，用于在无溶剂条件下合成萘并恶嗪酮。
• Synthesis of 1,2-dihydro-1-arylnaphtho[1,2-e][1,3]oxazine-3-one catalyzed by pyridinium-based ionic liquid
  作者：Fang Dong、Yang Li-fang、Yang Jin-ming

  DOI：10.1007/s11164-012-0776-6

  日期：2013.7

  Some pyridinium-based functionalized ionic liquids have been used as novel catalysts for the synthesis of 1,2-dihydro-1-arylnaphtho[1,2-e][1,3]oxazine-3-one derivatives via the one-pot multi-component condensation of β-naphthol, aromatic aldehydes, and urea under solvent-free conditions, to afford good to excellent yields ranging from 76 to 91 % within 60 min. A possible mechanism to account for the reaction is proposed.

  一些基于吡啶鎓的功能化离子液体已被用作新型催化剂，通过一锅法合成1,2-二氢-1-芳基萘并[1,2-e][1,3]恶嗪-3-酮衍生物。 β-萘酚、芳香醛和脲在无溶剂条件下进行组分缩合，可在 60 分钟内实现从 76 % 到 91 % 的良好收率。提出了解释该反应的可能机制。
• A novel three-component one-pot reaction involving β-naphthol, aldehydes, and urea promoted by TMSCl/NaI
  作者：Gowravaram Sabitha、K. Arundhathi、K. Sudhakar、B. S. Sastry、J. S. Yadav

  DOI：10.1002/jhet.328

  日期：——

  Amidoalkyl naphthol derivatives have been synthesized in good yields in a one‐pot condensation of β‐naphthol, aromatic aldehydes and urea in presence of TMSCl/NaI at room temperature. Ring closure of amidoalkyl naphthol derivatives occurred at 140°C to afford 1,2‐dihydro‐1‐arylnaphtho[1,2‐e] [1,3]oxazin‐3‐one derivatives. J. Heterocyclic Chem., (2010).

  在室温下，在TMSCl / NaI存在下，β-萘酚，芳族醛和尿素的一锅缩合反应可合成高收率的氨基烷基萘酚衍生物。酰胺烷基萘酚衍生物在140℃下闭环，得到1,2-二氢-1-芳基萘[1,2-e] [1,3]恶嗪-3-酮衍生物。J.杂环化​​学。（2010）。