5-chloro-3-(prop-2-yn-1-yl)-1,3-benzoxazol-2(3H)-one | 142429-03-6

• 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: 5-chloro-3-(prop-2-yn-1-yl)-1,3-benzoxazol-2(3H)-one
• 英文别名: 3-propargyl-5-chlorobenzoxazol-2-one；5-chloro-3-prop-2-ynyl-1,3-benzoxazol-2-one
• CAS: 142429-03-6
• 化学式: C₁₀H₆ClNO₂
• 分子量: 207.616
• InChiKey: PEWMBJKQVZQEIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-chloro-3-(prop-2-yn-1-yl)-1,3-benzoxazol-2(3H)-one 在 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 作用下， 以 氮气 、 丙酮 为溶剂， 生成 3-(3-bromopropargyl)-5-chlorobenzoxazol-2-one
  参考文献：
  名称：

  Benzoxazolone compounds and the use thereof as microbicides

  摘要：

  公开了化学式为##STR1##的新化合物，其中X是I或Br；Y独立地选择自H、卤素、NO.sub.2、(C.sub.1 -C.sub.4)烷基、(C.sub.1 -C.sub.4)烷氧基、CN、OCO (C.sub.1 -C.sub.4)烷基、OCOPh或卤素(C.sub.1 -C.sub.4)烷基的群组中，这些化合物具有杀菌活性。

  公开号：

  US05102898A1
• 作为产物：
  描述：

  3-溴丙炔 、 氯唑沙宗 在 potassium carbonate 作用下， 以 丙酮 、 甲苯 为溶剂， 以10.5 g (86%)的产率得到5-chloro-3-(prop-2-yn-1-yl)-1,3-benzoxazol-2(3H)-one
  参考文献：
  名称：

  Benzoxazolone compounds and the use thereof as microbicides

  摘要：

  公开了化学式为##STR1##的新化合物，其中X是I或Br；Y独立地选择自H、卤素、NO.sub.2、(C.sub.1 -C.sub.4)烷基、(C.sub.1 -C.sub.4)烷氧基、CN、OCO (C.sub.1 -C.sub.4)烷基、OCOPh或卤素(C.sub.1 -C.sub.4)烷基的群组中，这些化合物具有杀菌活性。

  公开号：

  US05102898A1

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.
• Synthesis of novel 1,2,3-triazole based benzoxazolinones: Their TNF-α based molecular docking with in-vivo anti-inflammatory, antinociceptive activities and ulcerogenic risk evaluation
  作者：Saqlain Haider、M. Sarwar Alam、Hinna Hamid、Syed Shafi、Amit Nargotra、Priya Mahajan、Syed Nazreen、Arunasree M. Kalle、Chetna Kharbanda、Yakub Ali、Aftab Alam、Amulya K. Panda

  DOI：10.1016/j.ejmech.2013.10.032

  日期：2013.12

  A library of novel bis-heterocycles containing benzoxazolinone based 1,2,3-triazoles has been synthesized using click chemistry approach. The compound 3f exhibited potent selective COX-2 inhibition of 59.48% in comparison to standard drug celecoxib (6636% inhibition). The compound 31 showed significant (p < 0.001, 50.95%), TNF-alpha inhibitory activity as compared to indomethacin (p <0.001, 64.01%). The results of the carrageenan induced hind paw oedema showed that compounds 3a, 3f, 3i, 30, and 3e exhibited potent anti-inflammatory activity in comparison to Indomethacin. The molecular docking studies revealed that 3i exhibits strong inhibitory effect due to the extra stability of the complex because of an extra pi-pi bond. The histopathology report showed that none of the compounds caused gastric ulceration. (C) 2013 Elsevier Masson SAS. All rights reserved.
• US5102898A
  申请人：——

  公开号：US5102898A

  公开（公告）日：1992-04-07
• Benzoxazolone compounds and the use thereof as microbicides
  申请人：Rohm and Haas Company

  公开号：US05102898A1

  公开（公告）日：1992-04-07

  Novel compounds of the formula ##STR1## wherein X is I or Br; and Y is independently selected from the group consisting of H, halogen, NO.sub.2, (C.sub.1 -C.sub.4) alkyl, (C.sub.1 -C.sub.4) alkoxy, CN, OCO (C.sub.1 -C.sub.4) alkyl, OCOPh or halo (C.sub.1 -C.sub.4) alkyl, are disclosed as having microbicidal activity.

  公开了化学式为##STR1##的新化合物，其中X是I或Br；Y独立地选择自H、卤素、NO.sub.2、(C.sub.1 -C.sub.4)烷基、(C.sub.1 -C.sub.4)烷氧基、CN、OCO (C.sub.1 -C.sub.4)烷基、OCOPh或卤素(C.sub.1 -C.sub.4)烷基的群组中，这些化合物具有杀菌活性。