1,2-dihydro-1-phenylnaphtho[1,2-e][1,3]oxazin-3-one | 2911-24-2

• 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-phenylnaphtho[1,2-e][1,3]oxazin-3-one
• 英文别名: 1,2-dihydro-1-phenylnaphtho[1,2-e][1,3]oxazine-3-one；1-phenyl-1,2-dihydronaphtho[1,2-e][1,3]oxazin-3-one；1-phenyl-1,2-dihydrobenzo[f][1,3]benzoxazin-3-one
• CAS: 2911-24-2
• 化学式: C₁₈H₁₃NO₂
• 分子量: 275.307
• InChiKey: NUAMXCNOSNVFHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  methyl (2-hydroxynaphthalen-1-yl)(phenyl)methyl carbamate 在 1-丁基-3-甲基咪唑溴盐 作用下， 反应 0.5h， 以76%的产率得到1,2-dihydro-1-phenylnaphtho[1,2-e][1,3]oxazin-3-one
  参考文献：
  名称：

  Dabiri, Minoo; Delbari, Akram Sadat; Bazgir, Ayoob, Heterocycles, 2007, vol. 71, # 3, p. 543 - 548

  摘要：

  DOI：

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。
• A One-Pot Multicomponent Synthesis of Naphthoxazin-3-one Derivatives Using Amberlite IRA-400 Cl Resin as Green Catalyst
  作者：Gurusamy Harichandran、Parkunan Parameswari、Ponnusamy Shanmugam

  DOI：10.2174/1570178614666170811151040

  日期：2018.6.13

  An efficient Amberlite IRA-400 Cl resin catalyzed, solvent-free, one-pot synthesis of 1- aryl-1,2-dihydro-3H-naphtho[1,2-e][1,3]oxazin-3-ones via three-component reaction of arylaldehydes, urea, and β-naphthol are described. This method offers advantages such as easy work-up, low environmental impact, shortened reaction times, and high yields. The catalyst recovered was reused four times without significant

  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。
• Silica vanadic acid [SiO₂–VO(OH)₂] as an efficient heterogeneous catalyst for the synthesis of 1,2-dihydro-1-aryl-3H-naphth[1,2-e][1,3]oxazin-3-one and 2,4,6-triarylpyridine derivatives via anomeric based oxidation
  作者：Mohammad Ali Zolfigol、Maliheh Safaiee、Fatemeh Afsharnadery、Neda Bahrami-Nejad、Saeed Baghery、Sadegh Salehzadeh、Farahnaz Maleki

  DOI：10.1039/c5ra21392d

  日期：——

  efficiently catalyzed the synthesis of 1,2-dihydro-1-aryl-3H-naphth[1,2-e][1,3]oxazin-3-ones via reacting aromatic aldehydes and β-naphthol and urea under solvent-free condition. Additionally, 2,4,6-triarylpyridine derivatives were prepared through the condensation of ammonium acetate, aromatic aldehyde and various acetophenone in the presence of a catalytic amount of [SiO2–VO(OH)2] (SVA) under a same condition

  二氧化硅键合的钒酸[SiO 2 -VO（OH）2 ]（SVA）有效催化1,2-二氢-1-芳基-3 H-萘[1,2- e ] [1,3]恶嗪的合成通过在无溶剂条件下使芳族醛与β-萘酚和尿素反应生成-3-酮。另外，在催化量的[SiO 2 -VO（OH）2的存在下，通过乙酸铵，芳族醛和各种苯乙酮的缩合反应制备了2,4,6-三芳基吡啶衍生物。]（SVA）在相同条件下。为2,4,6-三芳基吡啶衍生物的合成的最后一步提出了一种新的基于端基的氧化方法，这一方法得到了理论研究的支持。因此，在合理设计，合成和应用新型氢化物释放化合物的过程中，所描述的新机理可以开辟新的前景。本方法的显着特征是反应时间短，产率高，后处理容易和SVA催化剂的可回收性。
• 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。