3-(4-chlorophenyl)-2H-1,3-benzoxazine-2,4(3H)-dione | 7133-85-9

• 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: 3-(4-chlorophenyl)-2H-1,3-benzoxazine-2,4(3H)-dione
• 英文别名: 3-(4-Chlrophenyl)-2H-1,3-benzoxazine-2,4(3H)-dione；3-(p-chlorophenyl)benzo[e]-1,3-oxazine-2,4-dione；3-(4-chloro-phenyl)-benzo[e][1,3]oxazine-2,4-dione；3-(4-Chlor-phenyl)-2,4-dioxo-3,4-dihydro-2H-1.3-benzoxazin；3-(4-Chlorphenyl)-1,3-benzoxazindion-2,4；3-(4-Chlorophenyl)-1,3-benzoxazine-2,4-dione
• CAS: 7133-85-9
• 化学式: C₁₄H₈ClNO₃
• 分子量: 273.675
• InChiKey: NQVADDMGQVZJHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：

  (2-氰基苯基)N-(4-氯苯基)氨基甲酸酯 在 盐酸 、 三乙胺 作用下， 以 乙醇 、 苯 为溶剂， 反应 76.0h， 生成 3-(4-chlorophenyl)-2H-1,3-benzoxazine-2,4(3H)-dione
  参考文献：
  名称：

  Petridou-Fischer, J.; Papadopoulos, E. P., Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 1159 - 1167

  摘要：

  DOI：

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。
• 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
• Palladium-Catalyzed Cyclocarbonylation of <i>o</i>-Iodophenols and 2-Hydroxy-3-iodopyridine with Heterocumulenes:  Regioselective Synthesis of Benzo[<i>e</i>]-1,3-oxazin-4-one and Pyrido[3,2-<i>e</i>]-1,3-oxazin-4-one Derivatives
  作者：Chitchamai Larksarp、Howard Alper

  DOI：10.1021/jo991256u

  日期：1999.12.1

  Benzo[e]-1,3-oxazin-2-imine-4-ones (3) were synthesized by cyclocarbonylation of o-iodophenols with carbodiimides in the presence of a catalytic amount of a palladium catalyst and 1,4-bis(diphenylphosphino)butane under CO pressure. Product yields are dependent on the nature of the substrate, catalyst, solvent, and base as well as phosphine ligand. Reaction of o-iodophenols with unsymmetrical carbodiimides affords benzo[e]-1,3-oxazin-2-imine-4-ones (11a-g) in good yield and usually in a completely regioselective manner. Benzo[e]-1,3-oxazin-2,4-diones (5) were obtained in good to excellent yields using the same procedure and a 1:2 ratio of o-iodophenol/isocyanate. Pyrido[3,2-e]-1,3-oxazin-4-ones (16) were isolated in fine yield using 2-hydroxy-3-iodopyridine instead of an iodophenol as reactant. The reaction mechanism is believed to involve in situ formation of a carbamate eater followed by palladium-catalyzed carbonylative amidation.