1-(4-(dimethylamino)phenyl)-1,2-dihydronaphtho[1,2-e][1,3]oxazin-3-one | 1234791-09-3

• 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-(4-(dimethylamino)phenyl)-1,2-dihydronaphtho[1,2-e][1,3]oxazin-3-one
• 英文别名: 1,2-Dihydro-1-(4-dimethylaminophenyl)-3h-naphtho[1,2-e][1,3]oxazine-3-one；1-[4-(dimethylamino)phenyl]-1,2-dihydrobenzo[f][1,3]benzoxazin-3-one
• CAS: 1234791-09-3
• 化学式: C₂₀H₁₈N₂O₂
• 分子量: 318.375
• InChiKey: FKNRPQTZSOXZHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (4-dimethylamino-benzyliden)-urea 、 2-萘酚 在 Amberlite IRA-400 Cl anion exchange resin 作用下， 以 neat (no solvent) 为溶剂， 生成 1-(4-(dimethylamino)phenyl)-1,2-dihydronaphtho[1,2-e][1,3]oxazin-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

• A one-pot synthesis of 1,2-dihydro-1-arylnaphtho[1,2-e][1,3]oxazine-3-ones catalyzed by iron(III) phosphate under solvent-free condition
  作者：Parisa Rahmani、Farahnaz K. Behbahani

  DOI：10.1080/15533174.2016.1216452

  日期：2017.5.4

  An efficient green route for the preparation of naphthoxazinones, applying a three-component one-pot condensation reaction of 2-naphthol, aromatic aldehyde, and urea in the presence of iron(III) phosphate under solvent-free conditions, has been developed. The present procedure offers several advantages such as short reaction time, simple workup, recovery, and reusability of the catalyst. In addition

  在无溶剂条件下，开发了一种有效的绿色路线，用于制备萘并恶嗪酮，在磷酸铁（III）存在下应用2-萘酚，芳族醛和尿素的三组分一锅缩合反应。本方法具有几个优点，例如反应时间短，后处理简单，回收和催化剂的可重复使用性。此外，还合成了一些新化合物，并且可以轻松扩大操作规模。
• Chlorotrimethylsilane-Promoted Synthesis of 1,2-Dihydro-1-Arylnaphtho [1,2-e] [1,3]Oxazine-3-Ones
  作者：Chenggang Jiang、Xin Geng、Zonglei Zhang、Hangxian Xu、Cunde Wang

  DOI：10.3184/030823409x12615635710356

  日期：2010.1

  Chlorotrimethylsilane (TMSCI) is effective as a catalyst for the preparation of 1,2-dihydro-1-arylnaphtho[1,2-e] [1,3]oxazine-3- ones using a one-pot condensation of 2-naphthol, aromatic aldehydes and urea in DMF as solvent. The reaction times, temperature, and catalyst amounts were varied.

  以 DMF 为溶剂，采用 2-萘酚、芳香醛和尿素的一锅缩合反应制备 1,2-二氢-1-芳基萘并[1,2-e] [1,3]oxazine-3- ones 时，三甲基氯硅烷（TMSCI）是一种有效的催化剂。反应时间、温度和催化剂用量各不相同。
• Guanidine Hydrochloride Catalyzed, Rapid and Efficient One-Pot Synthesis of Naphthoxazinones Under Solvent-Free Conditions
  作者：A. Olyaei、M. Sadeghpour、M. Zarnegar

  DOI：10.1007/s10593-013-1387-x

  日期：2013.12

  A novel method for the synthesis of 1-aryl-1,2-dihydro-3H-naphtho[1,2-e][1,3]oxazin-3-one derivatives employing one-pot three-component reaction of β-naphthol, aromatic aldehydes, and urea using a catalytic amount of guanidine hydrochloride under solvent-free thermal conditions is described. This method provides several advantages like clean and environmentally benign reaction, simple work-up procedure

  β-一锅三组分反应合成1-芳基-1,2-二氢-3 H-萘[1,2- e ] [1,3]恶嗪-3-酮衍生物的新方法描述了在无溶剂的热条件下使用催化量的盐酸胍的萘酚，芳族醛和尿素。该方法具有许多优点，例如干净且对环境无害的反应，简单的后处理程序，低成本，易于分离的产品，而无需通过柱色谱法进一步纯化，较短的反应时间和高收率。
• AgI nanoparticles as a remarkable catalyst in the synthesis of (amidoalkyl)naphthol and oxazine derivatives: an eco-friendly approach
  作者：Javad Safaei Ghomi、Safura Zahedi、Mohammad Ali Ghasemzadeh

  DOI：10.1007/s00706-014-1184-y

  日期：2014.7

  AgI nanoparticles were discovered to be an effectual heterogeneous nanocatalyst for the preparation of (amidoalkyl)naphthol and oxazine derivatives under solvent-free conditions. The advantages of the present approach are short reaction times, moderate temperature, premier yields, eco-friendly reaction conditions, simple purification and good reusability of the catalyst.
• Graphene oxide mediated solvent-free three component reaction for the synthesis of 1-amidoalkyl-2-naphthols and 1,2-dihydro-1-arylnaphth[1,2- e ][1,3]oxazin-3-ones
  作者：Annah Gupta、Dilpreet Kour、Vivek K. Gupta、Kamal K. Kapoor

  DOI：10.1016/j.tetlet.2016.09.067

  日期：2016.10

  The present report describes a solvent-free synthesis of 1-amidoalkyl-2-naphthols and 1,2-dihydro-1arylnaphth[1,2-e][1,3]oxazin-3-ones via one-pot multicomponent reaction of 2-naphthol, aryl/heteryl aldehyde, and amide/urea in presence of graphene oxide as an eco-benign heterogeneous catalyst in good to excellent yields. The catalyst is easily recoverable and reusable. (C) 2016 Elsevier Ltd. All rights reserved.