2-ethyl-4-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-one | 13212-61-8

• 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-ethyl-4-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-one
• 英文别名: 2-Aethyl-3,4-dihydro-4-hydroxy-3-oxo-2H-1,4-benzoxazin；2-ethyl-4-hydroxy-(2H)-1,4-benzoxazin-3(4H)-one；2-Et-D-DIBOA；2-ethyl-D-DIBOA；2-ethyl-4-hydroxy-4H-benzo[1,4]oxazin-3-one；2-Ethyl-4-hydroxy-1,4-benzoxazin-3-one
• CAS: 13212-61-8
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: VVTRVUOMIPLROC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-ethyl-4-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-one 生成 7-chloro-2-ethyl-4H-benzo[1,4]oxazin-3-one
  参考文献：
  名称：

  芳族羟胺和一些环异羟肟酸的制备及其与盐酸的反应

  摘要：

  2,3-二甲基-4-(邻硝基苯硫基)-1-苯基-3-吡唑啉-5-酮用硼氢化钠和钯-炭还原得到相应的羟胺。盐酸对该羟胺的作用产生对氯胺。以类似的方式，用盐酸处理一些 2H-1,4-苯并噻嗪和 -苯并恶嗪异羟肟酸导致形成 7-氯-2H-1,4-苯并噻嗪和 -苯并恶嗪内酰胺。

  DOI：

  10.1139/v70-306
• 作为产物：
  描述：

  2-(2-nitro-phenoxy)-butyric acid ethyl ester 在 sodium tetrahydroborate 、 palladium 10% on activated carbon 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以305 mg的产率得到2-ethyl-4-hydroxy-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

• 10.1039/d4cc02118e
  作者：Winter, Johannes、Lühr, Susan、Hochadel, Kyra、Gálvez-Vázquez, María de Jesús、Prenzel, Tobias、Schollmeyer, Dieter、Waldvogel, Siegfried R.

  DOI：10.1039/d4cc02118e

  日期：——

  The electrochemical reduction of nitroarenes allows direct access to manifold nitrogen containing heterocycles. This work reports the simple and direct electro-organic synthesis of 18 different examples of 2H,4H-4-hydroxy-1,4-benzoxazin-3-ones in up to 81% yield. The scalability of the method was demonstrated on a gram-scale.

  硝基芳烃的电化学还原允许直接获得多种含氮杂环。这项工作报道了 18 种不同的 2 H ,4 H -4-羟基-1,4-苯并恶嗪-3-酮的简单直接的有机电合成，产率高达 81%。该方法的可扩展性在克级上得到了证明。
• 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.
• 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
• Preparation of an aromatic hydroxylamine and some cyclic hydroxamic acids, and their reaction with hydrochloric acid
  作者：R. T. Coutts、N. J. Pound

  DOI：10.1139/v70-306

  日期：1970.6.15

  reduction of 2,3-dimethyl-4-(o-nitrophenylthio)-1-phenyl-3-pyrazolin-5-one by sodium borohydride and palladium–charcoal gave the corresponding hydroxylamine. The action of hydrochloric acid on this hydroxylamine gave the p-chloroamine. In a similar manner, treatment of some 2H-1,4-benzothiazine and -benzoxazine hydroxamic acids with hydrochloric acid resulted in the formation of 7-chloro-2H-1,4-benzothiazine

  2,3-二甲基-4-(邻硝基苯硫基)-1-苯基-3-吡唑啉-5-酮用硼氢化钠和钯-炭还原得到相应的羟胺。盐酸对该羟胺的作用产生对氯胺。以类似的方式，用盐酸处理一些 2H-1,4-苯并噻嗪和 -苯并恶嗪异羟肟酸导致形成 7-氯-2H-1,4-苯并噻嗪和 -苯并恶嗪内酰胺。