3-(4-bromo-phenyl)-6-chloro-benzo[e][1,3]oxazine-2,4-dione | 18655-97-5

• 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-bromo-phenyl)-6-chloro-benzo[e][1,3]oxazine-2,4-dione
• 英文别名: 3-(4-Bromophenyl)-6-chloro-1,3-benzoxazine-2,4-dione
• CAS: 18655-97-5
• 化学式: C₁₄H₇BrClNO₃
• 分子量: 352.571
• InChiKey: WNRIVXRGBGKLET-UHFFFAOYSA-N

物化性质

• 沸点：
  490.6±55.0 °C(Predicted)
• 密度：
  1.730±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 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：

  3-(4-bromo-phenyl)-6-chloro-benzo[e][1,3]oxazine-2,4-dione 在 tetraphosphorus decasulfide 作用下， 反应 0.33h， 以47%的产率得到3-(4-Bromophenyl)-6-chloro-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：

  N-(4-溴苯基)-5-氯-2-羟基苯甲酰胺 、 氯甲酸乙酯 在 吡啶 作用下， 反应 1.0h， 以60%的产率得到3-(4-bromo-phenyl)-6-chloro-benzo[e][1,3]oxazine-2,4-dione
  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

文献信息

• 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.
• 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.