5-[1-Bromo-1-phenyl-meth-(Z)-ylidene]-pyrrolidine-2,3,4-trione | 299957-03-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-[1-Bromo-1-phenyl-meth-(Z)-ylidene]-pyrrolidine-2,3,4-trione
• 英文别名: (5Z)-5-[bromo(phenyl)methylidene]pyrrolidine-2,3,4-trione
• CAS: 299957-03-2
• 化学式: C₁₁H₆BrNO₃
• 分子量: 280.078
• InChiKey: YPJDVRILBOUJBO-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二氮杂甲苯 、 5-[1-Bromo-1-phenyl-meth-(Z)-ylidene]-pyrrolidine-2,3,4-trione 以 1,4-二氧六环 、 正己烷 为溶剂， 反应 1.0h， 以50%的产率得到3-Benzyloxy-6-[1-bromo-1-phenyl-meth-(Z)-ylidene]-4-phenyl-1,6-dihydro-pyridine-2,5-dione
  参考文献：
  名称：

  Grevellin Analogs with Affinity to theN-Methyl-D-aspartate (Glycine Site) Receptor, a Novel Lead Structure

  摘要：

  A series of piperidine-2,3,5-triones (azagrevellins) has been prepared. A new synthesis has been introduced using the rearrangement of spiroepoxides in the presence of triethyloxonium tetrafluoroborate. The binding affinity toward the N-methyl-D-aspartate (glycine site) receptor has been measured to provide a basis for more detailed structure-activity studies. Azagrevellin 18d showed the highest binding potency.

  DOI：

  10.1002/1521-4184(20007)333:7<211::aid-ardp211>3.0.co;2-9
• 作为产物：
  描述：

  5-[1-Bromo-1-phenyl-meth-(Z)-ylidene]-3-isopropylidene-pyrrolidine-2,4-dione 在 sodium hydroxide 、 硫酸 、 双氧水 、 碘 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 0.75h， 生成 5-[1-Bromo-1-phenyl-meth-(Z)-ylidene]-pyrrolidine-2,3,4-trione
  参考文献：
  名称：

  Grevellin Analogs with Affinity to theN-Methyl-D-aspartate (Glycine Site) Receptor, a Novel Lead Structure

  摘要：

  A series of piperidine-2,3,5-triones (azagrevellins) has been prepared. A new synthesis has been introduced using the rearrangement of spiroepoxides in the presence of triethyloxonium tetrafluoroborate. The binding affinity toward the N-methyl-D-aspartate (glycine site) receptor has been measured to provide a basis for more detailed structure-activity studies. Azagrevellin 18d showed the highest binding potency.

  DOI：

  10.1002/1521-4184(20007)333:7<211::aid-ardp211>3.0.co;2-9

文献信息

• SUBSTITUIERTE PYRROLIDIN-2,3,4-TRION-DERIVATE WIRKSAM ALS NMDA-REZEPTOR-ANTAGONISTEN
  申请人：Grünenthal GmbH

  公开号：EP1200400B1

  公开（公告）日：2004-09-29
• Grevellin Analogs with Affinity to theN-Methyl-D-aspartate (Glycine Site) Receptor, a Novel Lead Structure
  作者：Hermann Poschenrieder、Georg Höfner、Hans-Dietrich Stachel

  DOI：10.1002/1521-4184(20007)333:7<211::aid-ardp211>3.0.co;2-9

  日期：2000.7

  A series of piperidine-2,3,5-triones (azagrevellins) has been prepared. A new synthesis has been introduced using the rearrangement of spiroepoxides in the presence of triethyloxonium tetrafluoroborate. The binding affinity toward the N-methyl-D-aspartate (glycine site) receptor has been measured to provide a basis for more detailed structure-activity studies. Azagrevellin 18d showed the highest binding potency.