2-ethyl-6-methyl-4H-benzo[d][1,3]oxazin-4-one | 157834-02-1

• 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-6-methyl-4H-benzo[d][1,3]oxazin-4-one
• 英文别名: 2-Ethyl-6-methyl-3,1-benzoxazin-4-one
• CAS: 157834-02-1
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: HZFYNVUBGNOXKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-ethyl-6-methyl-4H-benzo[d][1,3]oxazin-4-one 在 N-甲基吡咯烷酮 、 溴 、 sodium acetate 、 溶剂黄146 作用下， 生成
  参考文献：
  名称：

  Quinazolinone fungal efflux pump inhibitors. Part 2: In vitro structure–activity relationships of (N-methyl-piperazinyl)-containing derivatives

  摘要：

  Structure-activity relationships of a novel series of fungal efflux pump inhibitors with respect to potentiation of the activity of fluconazole against strains of Candida albicans and Candida glabrata over-expressing ABC-type efflux pumps are systematically explored. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.071
• 作为产物：
  描述：

  2-氨基-5-甲基苯甲酸 、 丙酸酐 反应 2.0h， 以76%的产率得到2-ethyl-6-methyl-4H-benzo[d][1,3]oxazin-4-one
  参考文献：
  名称：

  1H和13C NMR光谱研究了一些4H-3,1-苯并恶嗪-4-酮及其2-酰基氨基苯甲酸前体。

  摘要：

  给出了十二个4H-3,1-苯并恶嗪-4-酮及其酰基氨基苯甲酸前体的1H和13C NMR光谱。这两个系列化合物之间的区别最好通过高频羰基区域中的特征性J（CH）偶联相互作用实现。还研究了一些4H-吡啶并[2,3-d] [1,3]恶嗪-4-酮，并对一些较早的文献进行了修订。

  DOI：

  10.1016/s1386-1425(99)00206-1

文献信息

• 4H-Benzo[d][1,3]oxazin-4-ones and Dihydro Analogs from Substituted Anthranilic Acids and Orthoesters
  作者：Joel K. Annor-Gyamfi、Richard A. Bunce

  DOI：10.3390/molecules24193555

  日期：——

  (±)-2-alkyl/aryl-2-ethoxy-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-ones. The formation of the dihydro analogs correlated with the electron density on the aromatic ring: Electron-donating groups favored the 4H- benzo[d][1,3]oxazin-4-ones, while electron-withdrawing groups tended to favor the dihydro product. Substituting a pyridine ring for the benzene ring in the substrate acid suppressed the reaction.

  已开发出一种制备 2-烷基和 2-芳基-4H-苯并[d][1,3]恶嗪-4-酮（也称为 4H-3,1-苯并恶嗪-4-酮）的一锅法，并学习了。该方法包括芳基取代的邻氨基苯甲酸与原酸酯在乙醇中的乙酸催化反应。此外，我们还研究了微波条件下的反应。并非所有底物都能成功产生目标杂环，因为一些反应未能进行最终消除。该过程导致 (±)-2-烷基/芳基-2-乙氧基-1,2-二氢-4H-苯并[d][1,3]恶嗪-4-酮的分离。二氢类似物的形成与芳环上的电子密度相关：给电子基团有利于 4H-苯并[d][1,3]恶嗪-4-酮，而吸电子基团有利于二氢产物.
• 1H and 13C NMR spectral studies of some 4H-3,1-benzoxazin-4-ones and their 2-acylaminobenzoic acid precursors
  作者：Alan G Osborne、Zia Goolamali

  DOI：10.1016/s1386-1425(99)00206-1

  日期：2000.5

  The 1H and 13C NMR spectra of twelve 4H-3,1-benzoxazine-4-ones and of their acylaminobenzoic acid precursors are presented. Differentiation between these two series of compounds is best achieved through the characteristic J(CH) coupling interactions in the high frequency carbonyl region. Some 4H-pyrido[2,3-d][1,3]oxazin-4-ones have also been studied and some earlier literature assignments revised.

  给出了十二个4H-3,1-苯并恶嗪-4-酮及其酰基氨基苯甲酸前体的1H和13C NMR光谱。这两个系列化合物之间的区别最好通过高频羰基区域中的特征性J（CH）偶联相互作用实现。还研究了一些4H-吡啶并[2,3-d] [1,3]恶嗪-4-酮，并对一些较早的文献进行了修订。
• Fragment-Based Design of Novel Quinazolinon Derivatives as Human Acrosin Inhibitors
  作者：Weiwei Ning、Ju Zhu、Canhui Zheng、Xuefei Liu、Yunlong Song、Youjun Zhou、Xiaomeng Zhang、Ling Zhang、Chunquan Sheng、Jiaguo Lv

  DOI：10.1111/cbdd.12106

  日期：2013.4

  Human acrosin is a promising target for the male contraceptives. On the basis of the active site of human acrosin, a series of novel quinazolinon compounds were designed by a fragment docking and growing strategy. In vitro anti‐acrosin assay revealed that all the compounds showed potent human acrosin inhibitory activities. In particular, compounds 5c and 5g are more active than the known inhibitors. Molecular docking studies revealed that the quinazolinon inhibitors interacted with human acrosin mainly through hydrogen bonding and hydrophobic interactions. The binding mode was also consistent with the structure–activity relationships. The quinazolinon derivatives in this study can serve as new lead structure for the development of novel male contraceptives.
• El-Naser Ossman; El-Sayed Barakat, Arzneimittel-Forschung/Drug Research, 1994, vol. 44, # 8, p. 915 - 919
  作者：El-Naser Ossman、El-Sayed Barakat

  DOI：——

  日期：——
• El-Naser Ossman A. R., El-Sayed Barakat S., Arzneim.-Forsch, 44 (1994) N 8, S 915-919
  作者：El-Naser Ossman A. R., El-Sayed Barakat S.

  DOI：——

  日期：——