2-propyl-4-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-one

• 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-propyl-4-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-one
• 英文别名: 2-propyl-D-DIBOA；2-Pr-D-DIBOA；4-hydroxy-2-propyl-1,4-benzoxazin-3-one
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: YFGABHBLFBPNDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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-溴戊酸乙酯 在 potassium methanolate 、 氯化铵 、 锌 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 2.5h， 生成 2-propyl-4-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-one
  参考文献：
  名称：

  Synthesis and antimicrobial activity of some new 4-hydroxy-2H-1,4-benzoxazin-3(4H)-ones

  摘要：

  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.

  DOI：

  10.1016/s0014-827x(00)00098-7

文献信息

• Synthesis and antimicrobial activity of some benzoxazinoids derivatives of 2-nitrophenol and 3-hydroxy-2-nitropyridine
  作者：William Gustavo Lima、Flávio José dos Santos、Adriana Cristina Soares、Francisco A. Macías、José M. G. Molinillo、Jaqueline Maria Siqueira Ferreira、João Máximo de Siqueira

  DOI：10.1080/00397911.2018.1554146

  日期：2019.1.17

  by palladium on carbon. Next, the biological assays showed that pyridoxazinone serie has a good antibacterial activity, especially against Enterococcus faecalis (Minimum inhibitory concentration—MIC: 7.8-15.6 μg.mL−1) and Acinetobacter baumannii (MIC 31.25-125 μg.mL−1). Antifungal activity, in turn, was related to compound 2e which showed a MIC of 62.5 μg.mL−1 against Candida albicans, Candida glabrata

  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
• 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.