3-butyl-3,4-dihydro-2H-benzo[e]-1,3-oxazine | 478347-90-9

• 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-butyl-3,4-dihydro-2H-benzo[e]-1,3-oxazine
• 英文别名: 3-butyl-3,4-dihydro-2H-1,3-benzoxazine；2H-1,3-Benzoxazine, 3-butyl-3,4-dihydro-；3-butyl-2,4-dihydro-1,3-benzoxazine
• CAS: 478347-90-9
• 化学式: C₁₂H₁₇NO
• 分子量: 191.273
• InChiKey: MCGKDDMUEPJECG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  N,N-bis(1H-1,2,3-benzotriazol-1-ylmethyl)butan-1-amine 、 苯酚 在 正丁基锂 、 四甲基乙二胺 、 zinc dibromide 作用下， 以 正己烷 、 环己烷 、 四氢呋喃 为溶剂， 反应 8.0h， 以70%的产率得到3-butyl-3,4-dihydro-2H-benzo[e]-1,3-oxazine
  参考文献：
  名称：

  A Novel Dilithiation Approach to 3,4-Dihydro-2H-1,3-benzothiazines, 3,4-Dihydro-2H-1,3-benzoxazines, and 2,3,4,5-Tetrahydro-1,3-benzothiazepines

  摘要：

  3,4-Dihydro-2H-1,3-benzothiazines 4, 3,4-dihydro-2H-1,3-benzoxazines 9, and 2,3,4,5-tetrahydro-1,3-benzothiazepines 6 were synthesized by directed ortho-lithiation of thiophenols and phenols and by side-chain lithiation of substituted thiophenols, respectively, in one-pot by reacting with N,N-bis[(benzotriazol-1-yl)methyl]amines 3 as 1,3-biselectrophile synthons.

  DOI：

  10.1021/jo020176e

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％）。
• Using Methanol as a Formaldehyde Surrogate for Sustainable Synthesis of <scp> <i>N</i> ‐Heterocycles </scp> via <scp>Manganese‐Catalyzed</scp> Dehydrogenative Cyclization
  作者：Zhihui Shao、Shanshan Yuan、Yibiao Li、Qiang Liu

  DOI：10.1002/cjoc.202100886

  日期：2022.5.15

  The development of an efficient and sustainable synthetic route for formaldehyde production from renewable feedstock, especially in combination with a subsequent transformation to straightforwardly construct valuable chemicals, is highly desirable. Herein, we report a novel manganese-catalyzed dehydrogenative cyclization of methanol as a formaldehyde surrogate with a variety of dinucleophiles for facile

  开发一种高效且可持续的从可再生原料生产甲醛的合成路线，尤其是结合随后的转化以直接构建有价值的化学品是非常可取的。在此，我们报告了一种新型的锰催化甲醇脱氢环化反应，作为甲醛替代物，其具有多种亲核试剂，可方便地合成N-杂环化合物。通过催化甲醇脱氢原位产生的甲醛可以被多种双亲核试剂选择性地捕获，以避免几种可能的副反应。这种转化的实用性通过其成功应用于合成13 C-标记的N-杂环使用13 CH 3 OH 作为容易获得的13 C-同位素试剂。
• Fluxing no-flow underfill composition containing benzoxazines
  申请人：National Starch and Chemical Investment Holding Corporation

  公开号：EP1621566B1

  公开（公告）日：2007-07-04
• A Novel Dilithiation Approach to 3,4-Dihydro-2<i>H</i>-1,3-benzothiazines, 3,4-Dihydro-2<i>H</i>-1,3-benzoxazines, and 2,3,4,5-Tetrahydro-1,3-benzothiazepines
  作者：Alan R. Katritzky、Yong-Jiang Xu、Ritu Jain

  DOI：10.1021/jo020176e

  日期：2002.11.1

  3,4-Dihydro-2H-1,3-benzothiazines 4, 3,4-dihydro-2H-1,3-benzoxazines 9, and 2,3,4,5-tetrahydro-1,3-benzothiazepines 6 were synthesized by directed ortho-lithiation of thiophenols and phenols and by side-chain lithiation of substituted thiophenols, respectively, in one-pot by reacting with N,N-bis[(benzotriazol-1-yl)methyl]amines 3 as 1,3-biselectrophile synthons.