2H-1,3-苯并噁嗪-2,4(3H)-二酮,6-氯-3-(3,4-二氯苯基)- | 1927-32-8

• 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,6-氯-3-(3,4-二氯苯基)-
• 英文名称: 6-chloro-3-(3,4-dichloro-phenyl)-benzo[e][1,3]oxazine-2,4-dione
• 英文别名: 6-Chloro-3-(3,4-dichlorophenyl)-1,3-benzoxazine-2,4-dione
• CAS: 1927-32-8
• 化学式: C₁₄H₆Cl₃NO₃
• 分子量: 342.566
• InChiKey: LJOXDIVVMLSNEJ-UHFFFAOYSA-N

物化性质

• 沸点：
  503.1±60.0 °C(Predicted)
• 密度：
  1.620±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 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

• 作为反应物：
  描述：

  2H-1,3-苯并噁嗪-2,4(3H)-二酮,6-氯-3-(3,4-二氯苯基)- 在 tetraphosphorus decasulfide 作用下， 反应 0.33h， 以31%的产率得到6-Chloro-3-(3,4-dichlorophenyl)-1,3-benzoxazine-2,4-dithione
  参考文献：
  名称：

  New groups of antimycobacterial agents: 6-chloro-3-phenyl-4-thioxo-2 -1,3-benzoxazine-2(3 )-ones and 6-chloro-3-phenyl-2 -1,3-benzoxazine-2,4(3 )-dithiones

  摘要：

  A series of 6-chloro-3-phenyl-4-thioxo-2H-1,3-benzoxazine-2(3H)-ones 3 and a series of 6-chloro-3-phenyl-2H-1,3-benzoxazine-2,4(3H)-dithiones 4 were synthesized by melting 6-chloro-3-phenyl-2H-1,3-benzoxazine-2,4 and its derivatives substituted on the phenyl ring 2 with tetraphosphorus decasulfide. Compounds 2c-e, 3 and 4 exhibited in vitro activity against Mycobacterium tuberculosis, M. kansasii (two strains) and M. avium better than or comparable to that of isoniazid. Replacement of the oxo group by a thioxo group at position 4 led to improvement in activity against M. tuberculosis and M. kansasii. The Free-Wilson method and procedure developed by the authors were used to analyse the structure-activity and structure-antimycobacterial profile relationships, respectively. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00174-4
• 作为产物：
  描述：

  3,4,5-三氯水杨苯胺 、 氯甲酸乙酯 在 吡啶 作用下， 以 乙腈 为溶剂， 生成 2H-1,3-苯并噁嗪-2,4(3H)-二酮,6-氯-3-(3,4-二氯苯基)-
  参考文献：
  名称：

  取代的3-苯基-1,3-苯并恶嗪-2,4-二酮及其抑菌活性。

  摘要：

  DOI：

  10.1021/jm00338a034

文献信息

• 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
• New groups of antimycobacterial agents: 6-chloro-3-phenyl-4-thioxo-2 -1,3-benzoxazine-2(3 )-ones and 6-chloro-3-phenyl-2 -1,3-benzoxazine-2,4(3 )-dithiones
  作者：Karel Waisser、Jiří Gregor、Lenka Kubicová、Věra Klimešová、Jiří Kuneš、Miloš Macháček、Jarmila Kaustová

  DOI：10.1016/s0223-5234(00)00174-4

  日期：2000.8

  A series of 6-chloro-3-phenyl-4-thioxo-2H-1,3-benzoxazine-2(3H)-ones 3 and a series of 6-chloro-3-phenyl-2H-1,3-benzoxazine-2,4(3H)-dithiones 4 were synthesized by melting 6-chloro-3-phenyl-2H-1,3-benzoxazine-2,4 and its derivatives substituted on the phenyl ring 2 with tetraphosphorus decasulfide. Compounds 2c-e, 3 and 4 exhibited in vitro activity against Mycobacterium tuberculosis, M. kansasii (two strains) and M. avium better than or comparable to that of isoniazid. Replacement of the oxo group by a thioxo group at position 4 led to improvement in activity against M. tuberculosis and M. kansasii. The Free-Wilson method and procedure developed by the authors were used to analyse the structure-activity and structure-antimycobacterial profile relationships, respectively. (C) 2000 Editions scientifiques et medicales Elsevier SAS.