2-phenyl-3-isoxazolidinone | 54246-02-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 2-phenyl-3-isoxazolidinone
• 英文别名: 2-Phenylisoxazolin-3-one；2-phenyl-1,2-oxazolidin-3-one
• CAS: 54246-02-5
• 化学式: C₉H₉NO₂
• 分子量: 163.176
• InChiKey: UGXYIQSQJGGMMK-UHFFFAOYSA-N

物化性质

• 沸点：
  242.2±23.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  1-tert-butoxycarbonyl-3-formyl-4,6-dichloroindole-2-carboxylic acid ethyl ester 、 2-phenyl-3-isoxazolidinone 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以16%的产率得到(E)-4,6-dichloro-3-(3-oxo-2-phenylisoxzolidin-4-ylidenemethyl)-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and pharmacological characterisation of a conformationally restrained series of indole-2-carboxylates as in vivo potent glycine antagonists

  摘要：

  After the identification of GV150526, the indole-2-carboxylate template was further explored in order to identify novel potential anti-stroke agents. In particular, the SAR of the side chain present at the C-3 position of the indole nucleus was widely studied. In this paper, the synthesis and the pharmacological profile of a further class of conformationally restricted analogues of GV150526 as in vitro and in vivo potent glycine antagonists is reported. In particular, a pyrazolidinone derivative was identified as a potent neuroprotective agent in animal models of cerebral ischaemia. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01141-7
• 作为产物：
  描述：

  N-(3-chloropropionyl)-N-phenylhydroxylamine 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以82%的产率得到2-phenyl-3-isoxazolidinone
  参考文献：
  名称：

  Synthesis and pharmacological characterisation of a conformationally restrained series of indole-2-carboxylates as in vivo potent glycine antagonists

  摘要：

  After the identification of GV150526, the indole-2-carboxylate template was further explored in order to identify novel potential anti-stroke agents. In particular, the SAR of the side chain present at the C-3 position of the indole nucleus was widely studied. In this paper, the synthesis and the pharmacological profile of a further class of conformationally restricted analogues of GV150526 as in vitro and in vivo potent glycine antagonists is reported. In particular, a pyrazolidinone derivative was identified as a potent neuroprotective agent in animal models of cerebral ischaemia. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01141-7

文献信息

• [EN] AZIRIDINE SYNTHESIS<br/>[FR] SYNTHÈSE D'AZIRIDINE
  申请人：AGENCY SCIENCE TECH & RES

  公开号：WO2009096907A1

  公开（公告）日：2009-08-06

  The invention relates to a process for making an aziridine, wherein an aldehyde, a nitroso compound and a Michael acceptor are reacted in the presence of an N-heterocyclic carbene (NHC) catalyst.

  该发明涉及一种制备环氮丙烷的方法，其中在N-杂环卡宾（NHC）催化剂的存在下，醛、亚硝基化合物和迈克尔受体发生反应。
• INDOLE DERIVATIVES AS NMDA ANTAGONISTS
  申请人：GLAXO WELLCOME S.p.A.

  公开号：EP0723541A1

  公开（公告）日：1996-07-31
• US5760059A
  申请人：——

  公开号：US5760059A

  公开（公告）日：1998-06-02
• US5962496A
  申请人：——

  公开号：US5962496A

  公开（公告）日：1999-10-05
• US6100289A
  申请人：——

  公开号：US6100289A

  公开（公告）日：2000-08-08