2H-1,3-苯并噁嗪-2,4(3H)-二酮,3-(4-溴苯基)- | 13563-07-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 中文名称: 2H-1,3-苯并噁嗪-2,4(3H)-二酮,3-(4-溴苯基)-
• 英文名称: 3-(4-Bromophenyl)-2H-1,3-benzoxazine-2,4(3H)-dione
• 英文别名: 3-(4-bromo-phenyl)-benzo[e][1,3]oxazine-2,4-dione；3-(4-bromo-phenyl)-benz[e][1,3]oxazine-2,4-dione；3-(4-Brom-phenyl)-benz[e][1,3]oxazin-2,4-dion；3-(4-Brom-phenyl)-2,4-dioxo-3,4-dihydro-2H-1.3-benzoxazin；3-(4-Bromophenyl)-1,3-benzoxazine-2,4-dione
• CAS: 13563-07-0
• 化学式: C₁₄H₈BrNO₃
• 分子量: 318.126
• InChiKey: BIUGQOJKNOAFDC-UHFFFAOYSA-N

物化性质

• 沸点：
  451.3±47.0 °C(Predicted)
• 密度：
  1.659±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(4-bromo-phenyl)-2-phenylimino-2,3-dihydro-benz[e][1,3]oxazin-4-one 在 aqueous acid 作用下， 生成 2H-1,3-苯并噁嗪-2,4(3H)-二酮,3-(4-溴苯基)-
  参考文献：
  名称：

  The Synthesis of Heterocyclic Compounds by Means of Isothiourea Ethers

  摘要：

  DOI：

  10.1021/ja01339a045

文献信息

• New Groups of Potential Antituberculotics: 3-Aryl-2H,4H-benz[e][1,3]oxazine-2,4-diones. Comparison of the Topliss Approach with Regression Analysis
  作者：Karel Waisser、Lenka Kubicová、Věra Klimešová、Želmíra Odlerová

  DOI：10.1135/cccc19932977

  日期：——

  3-Phenyl-2H,4H-benz[e][1,3]oxazine-2,4-dione (I) and its derivatives II - XI, substituted on the phenyl ring, can be regarded as a new group of potential antituberculotics. Their activity increases with increasing electron-accepting properties of the substituents. introduction of bromine into the position 6 also positively influences the activity. the compounds are active in vitro against Mycobacterium tuberculosis and M. kansasii. The activity of some of them (VIII, IX0 exceeds that of commercial tuberculostatics used as standards.

  3-苯基-2H,4H-苯[e][1,3]噁嗪-2,4-二酮(I)及其苯环上取代的衍生物II-XI，可视为一组新的潜在抗结核药物。随着取代基电子受体性质的增加，它们的活性也会增加。在位置6引入溴也会对活性产生积极影响。这些化合物在体外对结核分枝杆菌和堪萨斯分枝杆菌具有活性。其中一些化合物(VIII，IX)的活性超过了作为标准使用的商业抗结核药物。
• Multivariate Regression with Substituent Shift Increments. IV. 2-(4-X-Phenyl)-1,3-dihydro-2H-isoindole-1,3-diones and 3-(4-X-Phenyl)-3,4-dihydro-2H-1,3-benzoxazine-2,4-diones
  作者：Miroslav Holík、Zdeněk Friedl、Karel Waisser、Jiří Gregor

  DOI：10.1135/cccc19991709

  日期：——

  Two series of para disubstituted benzenes were studied: 2-(4-X-phenyl)-1,3-dihydro- 2H-isoindole-1,3-diones (1) and 3-(4-X-phenyl)-3,4-dihydro-2H-1,3-benzoxazine-2,4-diones (2). Their ¹H and ¹³C chemical shifts were correlated with substituent shift increments (SSI) a_j and z_j, respectively. For ¹³C chemical shifts, all four z_j values, z_i, z_o, z_m, and z_p, were used to check the assignment and to find out possible variables for improvement of regression equations. Significant deviations from plain additivity were observed in the case of δ_H3 and δ_C3 chemical shifts. This can be explained by changes in diamagnetic anisotropy contribution induced by different twist of 4-substituent from the benzene plane caused by variable substituent in position 1.

  研究了两组para二取代苯：2-(4-X-苯基)-1,3-二氢-2H-异吲哚-1,3-二酮(1)和3-(4-X-苯基)-3,4-二氢-2H-1,3-苯并噁嗪-2,4-二酮(2)。它们的¹H和¹³C化学位移与取代基位移增量(SSl) a_j和z_j相关。对于¹³C化学位移，所有四个z_j值，z_i，z_o，z_m和z_p，都被用来检查分配并找出可能改进回归方程的变量。在δ_H3和δ_C3化学位移的情况下观察到明显的偏离简单加性。这可以通过由位于位置1的可变取代基引起的苯环平面外4-取代基的不同扭曲引起的抗磁性异向贡献的变化来解释。
• Trifluoroacetic Acid-Mediated Denitrogenative <i>ortho</i>-Hydroxylation of 1,2,3-Benzotriazin-4(3<i>H</i>)-ones: A Metal-Free Approach
  作者：Kanagaraj Madasamy、Madasamy Hari Balakrishnan、Ramaraju Korivi、Subramaniyan Mannathan

  DOI：10.1021/acs.joc.2c00354

  日期：2022.7.1

  An efficient trifluoroacetic acid-mediated denitrogenative hydroxylation of 1,2,3-benzotriazin-4(3H)-ones is described. This metal-free approach is compatible with a wide range of 1,2,3-benzotriazin-4(3H)-ones, affording ortho-hydroxylated benzamides in good to high yields with a short reaction time. The reaction is believed to proceed via a benzene diazonium intermediate. The synthetic utility of

  描述了一种有效的三氟乙酸介导的 1,2,3-benzotriazin-4(3 H )-ones 的脱氮羟基化。这种不含金属的方法与多种 1,2,3-benzotriazin-4(3 H )-one相容，可在较短的反应时间内以良好至高产率提供邻羟基化苯甲酰胺。据信该反应通过苯重氮中间体进行。该反应的合成效用通过以良好收率制备抗微生物药物利肝素 C 和苯并恶嗪-2,4(3 H )-二酮类化合物得到成功证明。
• Wagner; Singer; Weuffen, Pharmazie, 1966, vol. 21, # 3, p. 161 - 166
  作者：Wagner、Singer、Weuffen

  DOI：——

  日期：——
• Substituted 3-Phenyl-1,3-benzoxazine-2,4-diones and their Bacteriostatic Activity
  作者：Raymond E. Stenseth、Joseph W. Baker、Daniel P. Roman

  DOI：10.1021/jm00338a034

  日期：1963.3