2-isopropoxy-6-(2-methylpyrrolidin-1-yl)-4-trifluoromethylquinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-isopropoxy-6-(2-methylpyrrolidin-1-yl)-4-trifluoromethylquinoline
• 英文别名: 6-(2-Methylpyrrolidin-1-yl)-2-propan-2-yloxy-4-(trifluoromethyl)quinoline
• 化学式: C₁₈H₂₁F₃N₂O
• 分子量: 338.373
• InChiKey: AHMNBWOIXILYEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  25.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-isopropoxy-6-(2-methylpyrrolidin-1-yl)-4-trifluoromethylquinoline 在 盐酸 、 溶剂黄146 作用下， 以100%的产率得到(+/-)-6-(2-Methyl-1-pyrrolidino)-4-trifluoromethyl-2(1H)-quinolinone
  参考文献：
  名称：

  Substituted 6-(1-Pyrrolidine)quinolin-2(1H)-ones as Novel Selective Androgen Receptor Modulators

  摘要：

  The androgen receptor is a ligand inducible transcription factor that is involved in a broad range of physiological functions. Here we describe the discovery of a new class of orally available selective androgen receptor modulators. The lead compound, 6-[(2R,5R)-2-methyl-5-((R)-2,2,2-trifluoro- 1-hydroxyethyl)pyrrolidin-1-yl]-4-trifluoromethylquinolin-2(1H)-one (6a), showed excellent anabolic activity in muscle with reduced effect on the prostate in a rat model of hypogonadism. The compound also improved bone strength in a rat model of post-menopausal osteoporosis.

  DOI：

  10.1021/jm070231h
• 作为产物：
  描述：

  6-bromo-2-isopropoxy-4-(trifluoromethyl)quinoline 、 2-甲基吡咯烷 在 tris-(dibenzylideneacetone)dipalladium(0) caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以22%的产率得到2-isopropoxy-6-(2-methylpyrrolidin-1-yl)-4-trifluoromethylquinoline
  参考文献：
  名称：

  Substituted 6-(1-Pyrrolidine)quinolin-2(1H)-ones as Novel Selective Androgen Receptor Modulators

  摘要：

  The androgen receptor is a ligand inducible transcription factor that is involved in a broad range of physiological functions. Here we describe the discovery of a new class of orally available selective androgen receptor modulators. The lead compound, 6-[(2R,5R)-2-methyl-5-((R)-2,2,2-trifluoro- 1-hydroxyethyl)pyrrolidin-1-yl]-4-trifluoromethylquinolin-2(1H)-one (6a), showed excellent anabolic activity in muscle with reduced effect on the prostate in a rat model of hypogonadism. The compound also improved bone strength in a rat model of post-menopausal osteoporosis.

  DOI：

  10.1021/jm070231h