3-(but-3-en-1-yl)-5-chloro-1,3-benzoxazol-2(3H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 3-(but-3-en-1-yl)-5-chloro-1,3-benzoxazol-2(3H)-one
• 英文别名: 3-But-3-enyl-5-chloro-1,3-benzoxazol-2-one；3-but-3-enyl-5-chloro-1,3-benzoxazol-2-one
• 化学式: C₁₁H₁₀ClNO₂
• 分子量: 223.659
• InChiKey: DKJXRDBQYPHUIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-溴-1-丁烯 、 氯唑沙宗 在 cesium fluoride-celite 作用下， 以 四氢呋喃 为溶剂， 反应 4.17h， 以88%的产率得到3-(but-3-en-1-yl)-5-chloro-1,3-benzoxazol-2(3H)-one
  参考文献：
  名称：

  CsF–Celite catalyzed facile N-alkylation of 2(3H)-benzoxazolones and antimicrobial properties of 2-substituted benzoxazole and 3-substituted-2(3H)-benzoxazolone derivatives

  摘要：

  The synthesis and antimicrobial activity studies of a new series of cyclic amine containing benzoxazoles and benzoxazolone-2(3H)-ones derivatives were described. The alkylation of benzoxazolone was carried out using cesium fluoride-Celite. The newly synthesized compounds with the influence of the induction of the cyclic amine moiety in the benzoxazole scaffold have been evaluated with respect to the antibacterial and antifungal activity. The 2-cyclic amine-1,3-benzoxazoles (5a-l), 5-chloro-3-alkyl substituted-1,3-benzoxazol-2(3H)-ones (8a-f), and 3-[3-(cyclic amine)propyl]-1,3-benzoxazol-2(3H)-ones (9a-f) were synthesized. These derivatives were tested for antibacterial and antifungal activity. Among the compounds tested, 8c and 9f showed moderate to good antibacterial and antifungal activity. Compound 8a showed good antifungal activity.

  DOI：

  10.1007/s00044-010-9367-5

文献信息

• CsF–Celite catalyzed facile N-alkylation of 2(3H)-benzoxazolones and antimicrobial properties of 2-substituted benzoxazole and 3-substituted-2(3H)-benzoxazolone derivatives
  作者：M. S. R. Murty、Kesur R. Ram、Rayudu Venkateswara Rao、J. S. Yadav、U. S. N. Murty、K. Pranay Kumar

  DOI：10.1007/s00044-010-9367-5

  日期：2011.6

  The synthesis and antimicrobial activity studies of a new series of cyclic amine containing benzoxazoles and benzoxazolone-2(3H)-ones derivatives were described. The alkylation of benzoxazolone was carried out using cesium fluoride-Celite. The newly synthesized compounds with the influence of the induction of the cyclic amine moiety in the benzoxazole scaffold have been evaluated with respect to the antibacterial and antifungal activity. The 2-cyclic amine-1,3-benzoxazoles (5a-l), 5-chloro-3-alkyl substituted-1,3-benzoxazol-2(3H)-ones (8a-f), and 3-[3-(cyclic amine)propyl]-1,3-benzoxazol-2(3H)-ones (9a-f) were synthesized. These derivatives were tested for antibacterial and antifungal activity. Among the compounds tested, 8c and 9f showed moderate to good antibacterial and antifungal activity. Compound 8a showed good antifungal activity.