4-hydroxy-2-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one | 13212-60-7

• 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: 4-hydroxy-2-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one
• 英文别名: Methyl-2 dihydro-3,4 hydroxy-4 oxo-3 benzoxazin-1,4；2-methyl-D-DIBOA；2-Me-D-DIBOA；4-hydroxy-2-methyl-4H-benzo[1,4]oxazin-3-one；4-hydroxy-2-methyl-1,4-benzoxazin-3-one
• CAS: 13212-60-7
• 化学式: C₉H₉NO₃
• 分子量: 179.175
• InChiKey: ZLWRCWXTDTUWRE-UHFFFAOYSA-N

物化性质

• 沸点：
  325.5±45.0 °C(Predicted)
• 密度：
  1.358±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(2-硝基苯氧基)丙酸乙酯 在 sodium tetrahydroborate 、 palladium 10% on activated carbon 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以600 mg的产率得到4-hydroxy-2-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one
  参考文献：
  名称：

  2-硝基苯酚和3-羟基-2-硝基吡啶类苯并恶嗪衍生物的合成及抗菌活性

  摘要：

  摘要 苯并恶嗪类 (BXs) 是禾本科物种中常见的生物碱，是一种天然防御物质，可用于开发新型抗菌剂。在这里，BXs 类似物是由 2-硝基苯酚（苯并恶嗪酮系列）和 3-羟基-2-硝基吡啶（吡哆嗪酮系列）合成的，并针对真菌和医学细菌进行了测试。为了使类似物官能化，对起始材料进行足够的亲核取代，然后由钯/碳催化的还原性环化。其次，生物测定表明吡哆嗪酮系列具有良好的抗菌活性，尤其是对粪肠球菌（最低抑菌浓度-MIC：7.8-15.6 μg.mL-1）和鲍曼不动杆菌（MIC 31.25-125 μg.mL-1）。反过来，抗真菌活性 与化合物 2e 相关，化合物 2e 对白色念珠菌、光滑念珠菌和热带念珠菌的 MIC 为 62.5 μg.mL-1。所有类似物都符合利平斯基的规则，并预计具有低毒性。图形概要

  DOI：

  10.1080/00397911.2018.1554146

文献信息

• Synthesis and antimicrobial activity of some new 4-hydroxy-2H-1,4-benzoxazin-3(4H)-ones
  作者：Seçkin Özden、Aydin Murat Öztürk、Hakan Göker、Nurten Altanlar

  DOI：10.1016/s0014-827x(00)00098-7

  日期：2000.12

  Some 4-hydroxy-2H-1,4-benzoxazin-3(4H)-ones were synthesized and evaluated for their antimicrobial activities against Staphylococcus aureus, Escherichia coli and Candida albicans. Compounds 9, and 10 exhibited the best activity against Candida albicans. (C) 2000 Published by Elsevier Science S.A. All rights reserved.
• Modified Benzoxazinones in the System <i>Oryza sativa</i>−<i>Echinochloa crus-galli</i>: An Approach to the Development of Biorational Herbicide Models
  作者：Francisco A. Macías、Nuria Chinchilla、Rosa M. Varela、José M. G. Molinillo、David Marín、João M. De Siqueira

  DOI：10.1021/jf802735m

  日期：2008.11.12

  The utility of benzoxazinones and some of their synthetic derivatives in the search for new leads for herbicide model development has been explored. The work described focuses on obtaining derivatives that present selectivity in the system Oryza sativa-Echinochloa crus-galli. To achieve this goal the influence of lipophilicity in this system has been studied by preparing 14 ester derivatives at the N-4 position of D-DIBOA along with other compounds with different functionalization and chain lengths at position C-2. These compounds have been tested in the aforementioned system, and the dose-response profiles have been compared. The most active compound was 2-ethyl-4-hydroxy(2H)-1,4-benzoxazin-3(4H)-one, which presented higher selectivity than the specific herbicide Cotanil-35. These results confirm the potential of D-DIBOA as a lead herbicide for the control of Echinochloa spp. in rice crops.
• Tallec,A. et al., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1971, vol. 273, p. 1378 - 1381
  作者：Tallec,A. et al.

  DOI：——

  日期：——
• US7521468B2
  申请人：——

  公开号：US7521468B2

  公开（公告）日：2009-04-21
• US7794761B2
  申请人：——

  公开号：US7794761B2

  公开（公告）日：2010-09-14