3,4-dihydro-3-(4-methoxyphenyl)-2H-naphtho[2,1-e][1,3]oxazine | 1250256-59-7

• 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: 3,4-dihydro-3-(4-methoxyphenyl)-2H-naphtho[2,1-e][1,3]oxazine
• 英文别名: 3-(4-Methoxyphenyl)-2,4-dihydrobenzo[h][1,3]benzoxazine；3-(4-methoxyphenyl)-2,4-dihydrobenzo[h][1,3]benzoxazine
• CAS: 1250256-59-7
• 化学式: C₁₉H₁₇NO₂
• 分子量: 291.349
• InChiKey: UHZLOOYTVCNPCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 萘酚 、 甲氧苯胺 在 Cu(II) immobilized on nano Fe₃O₄ at walnut shell 作用下， 以 neat (no solvent) 为溶剂， 反应 0.42h， 以82%的产率得到3,4-dihydro-3-(4-methoxyphenyl)-2H-naphtho[2,1-e][1,3]oxazine
  参考文献：
  名称：

  纳米Fe3O4@核桃壳/Cu(II)作为高效环保催化剂，用于无溶剂条件下一锅假三组分合成1,3-恶嗪衍生物

  摘要：

  在碱性介质中，将CuCl 2添加到Fe 3 O 4 @核桃壳/Cu( II )中，制备了一种环保型生物基磁性纳米催化剂Fe 3 O 4 @核桃壳/Cu(II)。采用β-萘酚、甲醛的一锅拟三组分反应合成了一系列2-芳基/烷基-2,3-二氢-1H-萘并[1,2- e ][1,3]恶嗪和各种胺，使用纳米Fe 3 O 4 @核桃壳/Cu( II ) 在60 °C、无溶剂条件下。通过外部磁铁将催化剂从反应混合物中除去，并可重复使用多次，其活性没有任何明显损失。该方案具有产率高、反应时间短、程序清洁方便、后处理简单以及使用环保催化剂等优点。

  DOI：

  10.1039/d0ra04282j

文献信息

• An efficient and green method for the synthesis of [1,3]oxazine derivatives catalyzed by thiamine hydrochloride (VB1) in water
  作者：Valmik D. Dhakane、Somnath S. Gholap、Umesh P. Deshmukh、Hemant V. Chavan、Babasaheb P. Bandgar

  DOI：10.1016/j.crci.2013.06.002

  日期：2014.5

  Résumé An efficient and convenient synthesis of 1,3-oxazine derivatives has been achieved by the one-pot, multicomponent condensation of α- or β-naphthol, an aniline and formaldehyde using thiamine hydrochloride (VB1) as a versatile biodegradable and reusable catalyst in water as a universal solvent.

  摘要 使用盐酸硫胺素 (VB1) 作为通用的可生物降解和可重复使用的催化剂，通过 α- 或 β-萘酚、苯胺和甲醛的一锅多组分缩合，实现了 1,3-恶嗪衍生物的高效、便捷合成。水作为通用溶剂。
• Novel and Efficient Microwave-Assisted Three Component Reaction for the Synthesis Ofoxazine Derivatives
  作者：Preeti Bansal、Nakueshwar Jasuja、Gajanand Sharma

  DOI：10.13005/ojc/320442

  日期：2016.8.25

  Oxazine derivatives can be prepared with yield upto 98% within a few minutes by an efficient and novel one pot microwave- assisted three- component reaction from 1-naphthol, various anilines and formalin using montmorillonite as the catalyst. The procedure is very simple, efficient and environmentally friendly as it does not use any toxic auxiliary or solvent. The key advantages of this process are

  通过使用蒙脱石作为催化剂，由1-萘酚，各种苯胺和福尔马林进行高效，新颖的一锅微波辅助三组分反应，可以在几分钟内以高达98％的产率制备恶嗪衍生物。该过程非常简单，高效且环境友好，因为它不使用任何有毒的助剂或溶剂。该方法的主要优点是收率高，反应时间短，后处理容易，并且采用非色谱法纯化产物。
• An Efficient Synthesis of 3,4-Dihydro-3-substituted-2H-naphtho[2,1-e][1,3]oxazine Derivatives Catalyzed by Zirconyl(IV) Chloride and Evaluation of its Biological Activities
  作者：Amol H. Kategaonkar、Swapnil S. Sonar、Rajkumar U. Pokalwar、Atul H. Kategaonkar、Bapurao B. Shingate、Murlidhar S. Shingare

  DOI：10.5012/bkcs.2010.31.6.1657

  日期：2010.6.20

  †An efficient and novel one-pot synthesis of new 3,4-dihydro-3-substituted-2H-naphtho[2,1-e][1,3]oxazine derivatives from 1-naphthol, various anilines and formalin at room temperature grinding is presented. The six-membered N,O-heterocyclic skeleton was constructed via zirconyl(IV) chloride promoted Mannich type reaction. In vitro antimicrobial activities of synthesized compounds have been investigated

  †在室温下从 1-萘酚、各种苯胺和福尔马林高效且新颖的一锅法合成新的 3,4-二氢-3-取代-2H-萘并[2,1-e][1,3]恶嗪衍生物磨削呈现。六元 N,O-杂环骨架是通过氯化锆 (IV) 促进的曼尼希型反应构建的。与标准药物相比，合成化合物的体外抗菌活性已针对革兰氏阳性枯草芽孢杆菌、革兰氏阴性大肠杆菌和两种真菌白色念珠菌和黑曲霉进行了研究。初步生物测定结果表明，一些标题化合物具有显着的抗菌和抗真菌活性。
• Polyethylene glycol (PEG) mediated expeditious synthetic route to 1,3-oxazine derivatives
  作者：Pravin V. Shinde、Amol H. Kategaonkar、Bapurao B. Shingate、Murlidhar S. Shingare

  DOI：10.1016/j.cclet.2011.01.011

  日期：2011.8

  Various 1,3-oxazine derivatives were synthesized in high yields, within shorter reaction times using PEG-400 as a safer medium/mediator. This synthetic route is exceedingly easy and avoids the use of acid/base catalysts. (C) 2011 Murlidhar S. Shingare. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Phenolic Naphthoxazines as Curing Promoters for Benzoxazines
  作者：Gizem Kaya、Baris Kiskan、Yusuf Yagci

  DOI：10.1021/acs.macromol.8b00218

  日期：2018.3.13

  The effect of phenolic hydroxyl bearing naphthoxazines as catalysts for the ring-opening polymerization (ROP) of simple 1,3-benzoxazines was investigated. The latent catalytic role of napthoxazines in the curing process of the mixtures was demonstrated by DSC and FT-IR investigations. It was found that phenolic naphthoxazines cause clear reduction in ROP temperature, particularly when electron-withdrawing groups are attached and an onset ROP temperature as low as 169 degrees C is attained. Thermal properties of the final polymers were also analyzed, and no significant effect of naphthoxazines on the thermal stability of the cured polybenzoxazines was observed.