2-苄基-1,3-二氢苯并[f][1,3]苯并恶嗪 | 6342-10-5

• 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-苄基-1,3-二氢苯并[f][1,3]苯并恶嗪
• 英文名称: 2-benzyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine
• 英文别名: 3,4-Dihydro-3-benzyl-1,3-naphthoxazin；2-benzyl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazine；2-Benzyl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazin；2-benzyl-1,3-dihydrobenzo[f][1,3]benzoxazine
• CAS: 6342-10-5
• 化学式: C₁₉H₁₇NO
• mdl: MFCD01426765
• 分子量: 275.35
• InChiKey: KYFAABULEGCMTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.157
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-苄基-1,3-二氢苯并[f][1,3]苯并恶嗪 、 乙酸酐 生成 N-benzyl-N-(2-hydroxy-[1]naphthylmethyl)-acetamide
  参考文献：
  名称：

  Condensation of Naphthols with Formaldehyde and Primary Amines¹

  摘要：

  DOI：

  10.1021/ja01134a039
• 作为产物：
  描述：

  1,3,5-三苄基六氢-1,3,5-三嗪 、 2-萘酚 生成 2-苄基-1,3-二氢苯并[f][1,3]苯并恶嗪
  参考文献：
  名称：

  Moehrle,H.; Scharf,U., Pharmazie, 1978, vol. 33, p. 784 - 790

  摘要：

  DOI：

文献信息

• One-pot three-component synthesis of dihydrobenzo- and naphtho[<i>e</i>]-1,3-oxazines in water
  作者：Bijoy P. Mathew、Mahendra Nath

  DOI：10.1002/jhet.147

  日期：2009.9

  A simple, green and efficient method has been developed for the synthesis of biologically and materially important dihydrobenzo/naphtho[e]-1,3-oxazines in good to excellent yields through a Mannich-type condensation cyclization reaction of aromatic alcohols with HCHO and primary amines in aqueous media at ambient temperature. J. Heterocyclic Chem., (2009).

  通过芳族醇与HCHO和伯醇的曼尼希式缩合环化反应，已开发出一种简单，绿色，有效的方法，以良好至极佳的产率合成具有生物学和物质重要性的二氢苯并/萘并[ e ] -1,3-恶嗪。在室温下在水性介质中的胺。J.杂环化​​学，（2009）。
• An eco-friendly synthesis and antimicrobial activities of dihydro-2H-benzo- and naphtho-1,3-oxazine derivatives
  作者：Bijoy P. Mathew、Awanit Kumar、Satyasheel Sharma、P.K. Shukla、Mahendra Nath

  DOI：10.1016/j.ejmech.2009.12.058

  日期：2010.4

  3]oxazin-3(4H)-yl)ethane derivatives was obtained through an eco-friendly Mannich type condensation–cyclization reaction of phenols or naphthols with formaldehyde and primary amines in water at ambient temperature. Preliminary in vitro antimicrobial activity of the synthesized compounds was assessed against six pathogenic fungi, two Gram-negative and two Gram-positive bacteria. Some of the screened compounds

  一系列3,4-二氢-2 H-苯并[e]-，2,3-二氢-1 H-萘[1,2-e]-，3,4-二氢-2 H-萘[2，通过生态友好的Mannich获得了1-e] [1,3]恶嗪和1,2-双（3,4-二氢苯并[e] [1,3]恶嗪-3（4 H）-基）乙烷衍生物室温下水中的酚类或萘类与甲醛和伯胺的缩合型环化反应。评估了合成化合物对六种致病真菌，两种革兰氏阴性细菌和两种革兰氏阳性细菌的初步体外抗菌活性。一些筛选出的化合物显示出显着的体外抗菌作用。铅化合物的细胞毒活性（2m，通过MTT法测定针对小鼠成纤维细胞系（L929）的2n，3c和3d）。分析结果表明，这些分子以25μg/ mL的浓度提供了L929细胞显着的活力（> 90％）。
• 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。