1-(4-hydroxy-3-methoxyphenyl)-1,2-dihydro-3H-naphtho[1,2-e][1,3]oxazin-3-one | 1333500-55-2

• 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-(4-hydroxy-3-methoxyphenyl)-1,2-dihydro-3H-naphtho[1,2-e][1,3]oxazin-3-one
• 英文别名: 1-(4-Hydroxy-3-methoxyphenyl)-1,2-dihydrobenzo[f][1,3]benzoxazin-3-one；1-(4-hydroxy-3-methoxyphenyl)-1,2-dihydrobenzo[f][1,3]benzoxazin-3-one
• CAS: 1333500-55-2
• 化学式: C₁₉H₁₅NO₄
• 分子量: 321.332
• InChiKey: FCWOZTUQHXXCIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  香草醛 、 尿素 、 2-萘酚 在 C₆₂H₄₂N₂O₈⁽²⁺⁾*2Br^(1-) 作用下， 以 乙腈 为溶剂， 以87%的产率得到1-(4-hydroxy-3-methoxyphenyl)-1,2-dihydro-3H-naphtho[1,2-e][1,3]oxazin-3-one
  参考文献：
  名称：

  二氧化硅负载法合成二聚溴化吡啶鎓

  摘要：

  摘要 在常规/二氧化硅支持的方法下合成具有柔性连接单元的吡啶鎓盐的二聚取代酯衍生物。固相方法由于无毒、无溶剂、易于后处理和较短的反应时间而远优于传统方法。合成的吡啶鎓盐的二聚酯衍生物在常规/方法下对制备恶嗪酮衍生物显示出优异的催化反应。图形概要

  DOI：

  10.1080/00397911.2020.1733611

文献信息

• 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。
• Recyclable nanoparticulate copper mediated synthesis of naphthoxazinones in PEG-400: a green approach
  作者：Ajeet Kumar、Amit Saxena、Manika Dewan、Arnab De、Subho Mozumdar

  DOI：10.1016/j.tetlet.2011.07.016

  日期：2011.9

  An efficient methodology employing copper nanoparticles for the preparation of 2-naphthol condensed 1,3-oxazinone derivatives employing one-pot condensation reaction in the presence of K2CO3 and copper nanoparticles in PEG-400 is described which offers several advantages, viz, high yields, clean reaction, short reaction times, recyclability of the catalyst and simple workup procedure. PEG-400 was found to be the best solvent out of a range of solvents examined for this scheme. Moreover, PEG could stabilize the nanoparticles from oxidation and thus could increase the catalyst efficiency by escalating the TON (Turn over Number) and TOF (Turn over Frequency) of the catalyst, making the protocol greener, eco-friendly and environmentally benign. (C) 2011 Elsevier Ltd. All rights reserved.