2-phenoxy>-N-ethylpyrrolidin-2-one | 95393-33-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-phenoxy>-N-ethylpyrrolidin-2-one
• 英文别名: 1-[2-[4-[(E)-1-(4-methoxyphenyl)-2-nitro-2-phenylethenyl]phenoxy]ethyl]pyrrolidin-2-one
• CAS: 95393-33-2
• 化学式: C₂₇H₂₆N₂O₅
• 分子量: 458.514
• InChiKey: OFHULEDSGVTZDY-CYYJNZCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  84.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (Z/E)-1-<4-(2-bromoethoxy)phenyl>-1-(4-methoxyphenyl)-2-phenyl ethene 在 氢氧化钾 、 硝酸 、 四丁基硫酸氢铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 7.5h， 生成 2-phenoxy>-N-ethylpyrrolidin-2-one
  参考文献：
  名称：

  Estrogen receptor binding and estrogenic/antiestrogenic effects of two new metabolites of nitromiphene, 2-[p-[2-nitro-1-(4-methoxyphenyl)-2-phenylvinyl]phenoxy]-N-ethylpyrrolidine

  摘要：

  Reduction of the triarylethylene antiestrogen 2-[p-[2-nitro-1-(4-methoxphenyl)-2-phenylvinyl]phenoxy]-N-ethylpyrrolidine (1) with sodium borohydride-stannous chloride afforded 2-(p-methoxyphenyl)-p'-(2-pyrrolidin-1-ylethoxy)deoxybenzoin (2). Incubation of 1 with rat cecal content suspension under aerobic or anaerobic conditions also resulted in the generation of 2. The lactam analogue of 1 (6) was prepared by condensation of 4-(2-bromoethoxy)-4'-methoxybenzophenone (3) with benzylmagnesium chloride, followed by dehydration, amidation with 2-pyrrolidinone, and nitration. A metabolite with chromatographic and spectral properties identical with those of 6 was found in extracts from incubation mixtures of 1 with phenobarbital-induced rat liver 9000g supernatant. Compound 2 did not exhibit appreciable binding to the rat uterine cytosol estrogen receptor at concentrations of up to 1 X 10(-6) M and had no estrogenic or antiestrogenic activity in the 3-day rat uterotropic assay. By contrast, 6 had estrogen receptor affinity somewhat greater than that of 1 and slightly greater estrogenic activity accompanied by reduced antiestrogenic activity in comparison with those of 1.

  DOI：

  10.1021/jm00366a008

文献信息

• Estrogen receptor binding and estrogenic/antiestrogenic effects of two new metabolites of nitromiphene, 2-[p-[2-nitro-1-(4-methoxyphenyl)-2-phenylvinyl]phenoxy]-N-ethylpyrrolidine
  作者：Peter C. Ruenitz、Jerome R. Bagley、Corwin M. Mokler

  DOI：10.1021/jm00366a008

  日期：1983.12

  Reduction of the triarylethylene antiestrogen 2-[p-[2-nitro-1-(4-methoxphenyl)-2-phenylvinyl]phenoxy]-N-ethylpyrrolidine (1) with sodium borohydride-stannous chloride afforded 2-(p-methoxyphenyl)-p'-(2-pyrrolidin-1-ylethoxy)deoxybenzoin (2). Incubation of 1 with rat cecal content suspension under aerobic or anaerobic conditions also resulted in the generation of 2. The lactam analogue of 1 (6) was prepared by condensation of 4-(2-bromoethoxy)-4'-methoxybenzophenone (3) with benzylmagnesium chloride, followed by dehydration, amidation with 2-pyrrolidinone, and nitration. A metabolite with chromatographic and spectral properties identical with those of 6 was found in extracts from incubation mixtures of 1 with phenobarbital-induced rat liver 9000g supernatant. Compound 2 did not exhibit appreciable binding to the rat uterine cytosol estrogen receptor at concentrations of up to 1 X 10(-6) M and had no estrogenic or antiestrogenic activity in the 3-day rat uterotropic assay. By contrast, 6 had estrogen receptor affinity somewhat greater than that of 1 and slightly greater estrogenic activity accompanied by reduced antiestrogenic activity in comparison with those of 1.