2-(4-甲基苯基)-1,3-二氢苯并[f][1,3]苯并恶嗪 | 6642-03-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 中文名称: 2-(4-甲基苯基)-1,3-二氢苯并[f][1,3]苯并恶嗪
• 英文名称: 2-p-Tolyl-2.3-dihydro-1H-naphth<1.2-e>-1.3-oxazin
• 英文别名: 2-(4-methylphenyl)-1,3-dihydrobenzo[f][1,3]benzoxazine
• CAS: 6642-03-1
• 化学式: C₁₉H₁₇NO
• 分子量: 275.35
• InChiKey: POMJJVLRTLUHHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  [(4-甲基苯基)氨基]乙酸乙酯 、 2-萘酚 在 tris(2,2'-bipyridyl)ruthenium dichloride 、 lipase B Candida antarctica 作用下， 以 水 、 乙腈 为溶剂， 反应 48.0h， 以62%的产率得到2-(4-甲基苯基)-1,3-二氢苯并[f][1,3]苯并恶嗪
  参考文献：
  名称：

  酶和光氧化还原顺序催化一锅合成1,3-恶嗪衍生物

  摘要：

  首次介绍了一种将可见光和酶催化结合在一个罐中的新策略，该策略用于从[小的α]-或[小的β]-萘酚和N-芳基甘氨酸乙酯合成1，3-恶嗪衍生物。

  DOI：

  10.1039/c6cy02682f

文献信息

• An Efficient One-Pot Strategies for the Synthesis of [1,3] Oxazine Derivatives
  作者：Sapkal, Suryakant B.、Shelke, Kiran F.、Shingate, Bapurao B.、Shingare, Murlidhar S.

  DOI：10.5012/jkcs.2010.54.4.437

  日期：2010.8.20

  수용액 속에서 $NaHSO_4$, TBAB (phase transfer catalyst), ionic liquid (IL) (1-butyl-3-methyl imidazolium hydrogen sulphate [bmim]$HSO_4$)를 사용하여, formalin, $\beta}$-naphthol, aromatic amines을 반응시켜서 대응하는 2,3-dihydro-2-phenyl-1Hnaphtho-[1,2-e] [1,3] oxazine 유도체를 합성할 수 있는 보다 친환경적이고, 수율이 좋고, 크로마토그래피 분리 방법을 사용하지 않는 합성 방법을 개발하였다. Sodium hydrogen sulphate ($NaHSO_4$), n-tetra butyl ammonium bromide (TBAB) as a phase transfer catalyst (PTC) in water, and 1-butyl-3-methyl imidazolium hydrogen sulphate [bmim]$HSO_4$ as ionic liquid (IL) has been used as a mild reaction promoter for the cyclocondensation of formalin, $\beta}$-naphthol and aromatic amines to afford respective 2,3-dihydro-2-phenyl-1H-naphtho-[1,2-e] [1,3] oxazine derivatives. The present protocols are greener, high yielding and involved the nonchromatographic isolation procedure.

  수용액속에서$NaHSO_4$，TBAB（相转移催化剂）、离子液体（1-丁基-3-甲基咪唑硫酸氢[bmim]$HSO_4$）、福尔马林、$\beta}$-萘酚、2,3- 二氢-2-苯基-1Hnaphtho-[1,2-e] [1,3] oxazine 유도체를 합성할 수 있는 보다 친환경적이고, 수율이 좋고, 크로마토그래피 분리 방법을 사용하지 않는 합성 방법을 개발하였다. 硫酸氢钠（$NaHSO_4$）、作为水中相转移催化剂（PTC）的正丁基溴化铵（TBAB）和作为离子液体（IL）的 1-丁基-3-甲基咪唑硫酸氢盐 [bmim]$HSO_4$ 被用作福尔马林环缩合的温和反应促进剂、$\beta}$-萘酚和芳香胺可分别生成 2,3-二氢-2-苯基-1H-萘并[1,2-e] [1,3] 恶嗪衍生物。本方案更环保、产率高，并采用了非色谱分离程序。
• 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。
• Ultrasound-Assisted One-Pot Synthesis of 1,3-Oxazine Derivatives Catalysed by BF₃–SiO₂ Under Neat Conditions
  作者：Mudumala Veeranarayana Reddy、Kwon Taek Lim、Jong Tae Kim、Yeon Tae Jeong

  DOI：10.3184/174751912x13371662613770

  日期：2012.7

  An efficient and environment-friendly method for the synthesis of 1,3-oxazine derivatives has been developed using the ultrasound-mediated condensation of 2-naphthol with formaldehyde and primary amines under solvent-free condition at room temperature in the presence of BF₃-SiO₂ to give the desired product in good to excellent yield. This procedure provides several advantages over current methods including a simple work-up, cost effectiveness, a reusable catalyst and shorter reaction times.

  在 BF3-SiO2 存在下，在室温无溶剂条件下，利用超声波介导 2-萘酚与甲醛和伯胺的缩合，开发出了一种高效、环保的 1,3- 恶嗪衍生物合成方法，并以良好甚至极佳的收率得到了所需产物。与目前的方法相比，该方法具有多个优点，包括操作简单、成本效益高、催化剂可重复使用以及反应时间更短。
• Nano-Fe₃O₄@walnut shell/Cu(<scp>ii</scp>) as a highly effective environmentally friendly catalyst for the one-pot <i>pseudo</i> three-component synthesis of 1,3-oxazine derivatives under solvent-free conditions
  作者：Arefeh Dehghani Tafti、Bi Bi Fatemeh Mirjalili

  DOI：10.1039/d0ra04282j

  日期：——

  in alkaline medium. A series of 2-aryl/alkyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazines were synthesized by the one-pot pseudo three-component reaction of β-naphthol, formaldehyde and various amines using nano-Fe3O4@walnut shell/Cu(II) at 60 °C under solvent-free conditions. The catalyst was removed from the reaction mixture by an external magnet and was reusable several times without any considerable

  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。
• Gum arabic-OPO₃H₂ as a new natural-based green catalyst for the one-pot pseudo-four-component synthesis of naphtho[1,2-<i>e</i>][1,3]oxazines
  作者：Sahar Saadat Hosseinikhah、Bi Bi Fatemeh Mirjalili、Naeimeh Salehi、Abdolahamid Bamoniri

  DOI：10.1039/d0ra07199d

  日期：——

  catalyst was investigated for the synthesis of naphtho-1,3-oxazines via a pseudo-four-component reaction of primary amines, formaldehyde, and 2-naphthol under the solvent-free grinding condition at room temperature using an electrical mortar-heater. The obtained results indicated that GA-OPO3H2 is a highly efficient green catalyst for the synthesis of naphtho[1,2-e][1,3]oxazines with high yields, simple workup

  以五氧化二磷与阿拉伯胶反应合成了阿拉伯胶-OPO 3 H 2 (GA-OPO 3 H 2 )作为一种独特的天然绿色催化剂。通过FT-IR、MAPPING、EDS、SEM、XRD、TGA等多种分析方法研究了催化剂的结构和性能。考察了上述催化剂在室温无溶剂研磨条件下，通过伯胺、甲醛和2-萘酚的准四组分反应合成萘并-1,3-恶嗪的效率。电砂浆加热器结果表明，GA-OPO 3 H 2是一种用于合成萘[1,2- e ][1,3]恶嗪的高效绿色催化剂，收率高，后处理简单，反应条件良好。