3-(4-fluorobenzyl)-2H-1,3-benzoxazine-2,4(3H)-dione

• 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-fluorobenzyl)-2H-1,3-benzoxazine-2,4(3H)-dione
• 英文别名: 3-[(4-Fluorophenyl)methyl]-1,3-benzoxazine-2,4-dione
• 化学式: C₁₅H₁₀FNO₃
• 分子量: 271.248
• InChiKey: WZHZJWRSRYZZIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  氯甲酸乙酯 、 N-(4-fluorobenzyl)-2-hydroxybenzamide 在 吡啶 作用下， 反应 1.0h， 以45%的产率得到3-(4-fluorobenzyl)-2H-1,3-benzoxazine-2,4(3H)-dione
  参考文献：
  名称：

  3-Benzyl-2H-1,3-benzoxazine-2,4(3H)-diones, a new group of antimycobacterial compounds against potentially pathogenic strains

  摘要：

  A series of derivatives of 3-benzyl-2H-benzoxazine-2,4(3H)-dione substituted in positions 6, 7 or 8 on the benzoxazine, and in positions 3 or 4 on the benzyl moiety was synthesized. The compounds were evaluated for in vitro antimycobacterial activity against Mycobacterium avium and two strains of Mycobacterium kansasii. The disadvantage of the compounds is in their low solubility in water. The antimycobacterial activity of N-benzylsalicylamides correlates with that of 3-benzyl-2H-1,3-benzoxazin-2,4(3H)-diones and depends on the partition coefficients and electronic indexes.

  DOI：

  10.1016/j.farmac.2003.07.004

文献信息

• 3-Benzyl-2H-1,3-benzoxazine-2,4(3H)-diones, a new group of antimycobacterial compounds against potentially pathogenic strains
  作者：Karel Waisser、Milan Peřina、Jiřı́ Kuneš、Vera Klimešová、Jarmila Kaustová

  DOI：10.1016/j.farmac.2003.07.004

  日期：2003.11

  A series of derivatives of 3-benzyl-2H-benzoxazine-2,4(3H)-dione substituted in positions 6, 7 or 8 on the benzoxazine, and in positions 3 or 4 on the benzyl moiety was synthesized. The compounds were evaluated for in vitro antimycobacterial activity against Mycobacterium avium and two strains of Mycobacterium kansasii. The disadvantage of the compounds is in their low solubility in water. The antimycobacterial activity of N-benzylsalicylamides correlates with that of 3-benzyl-2H-1,3-benzoxazin-2,4(3H)-diones and depends on the partition coefficients and electronic indexes.