2-(4-bromophenyl)-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine | 6638-96-6

• 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: 2-(4-bromophenyl)-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine
• 英文别名: 2-<4-Brom-phenyl>-2.3-dihydro-1H-naphth<1.2-e>-1.3-oxazin；2-(4-bromo-phenyl)-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazine；2-(4-Brom-phenyl)-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazin；1h-Naphth[1,2-e][1,3]oxazine, 2-(4-bromophenyl)-2,3-dihydro-；2-(4-bromophenyl)-1,3-dihydrobenzo[f][1,3]benzoxazine
• CAS: 6638-96-6
• 化学式: C₁₈H₁₄BrNO
• 分子量: 340.219
• InChiKey: YKGNBGUROQRSLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  2-萘酚 、 1,3,5-三(4-溴苯基)-1,3,5-三嗪 以 乙腈 为溶剂， 以76 %的产率得到2-(4-bromophenyl)-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine
  参考文献：
  名称：

  Construction of Diverse N-Heterocycles by Formal (3 + 3) Cycloaddition of Naphthol/Thionaphthol/Naphthylamine and 1,3,5-Triazinanes

  摘要：

  DOI：

  10.1021/acs.joc.2c01822

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％）。
• 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。