2-[(2-propenyloxy)]-1-(3-methylphenyl)ethanone | 1248176-99-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(2-propenyloxy)]-1-(3-methylphenyl)ethanone
• 英文别名: 1-(3-Methylphenyl)-2-prop-2-enoxyethanone
• CAS: 1248176-99-9
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: FCEDBUFOFXLHPO-UHFFFAOYSA-N

物化性质

• 沸点：
  296.3±28.0 °C(predicted)
• 密度：
  1.010±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  potassium cyanide 、 ammonium carbonate monohydrate 、 2-[(2-propenyloxy)]-1-(3-methylphenyl)ethanone 在 水 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 4-[(2-propenyloxy)methyl]-4-(3-methylphenyl)imidazolidine-2,5-dione
  参考文献：
  名称：

  Identification of a 4-(Hydroxymethyl)diarylhydantoin as a Selective Androgen Receptor Modulator

  摘要：

  Structural modification performed on a 4-methyl-4-(4-hydroxyphenyphyl)hydantoin series is described which resulted in the development of a new series of 4-(hydroxymethyl)diarylhydantoin analogues as potent, partial agonists of the human androgen receptor. This led to the identification of (S)-(-)-4-(4-(hydroxymethyl)-3-methyl-2,5-dioxo-4-phenylimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile ((S)-(-)-18a, GLPG0492) evaluated in vivo in a classical model of orchidectomized rat. In this model, (-)-18a exhibited anabolic activity on muscle, strongly dissociated from the androgenic activity on prostate after oral dosing. (-)-18a has very good pharmacokinetic properties, including bioavailability in rat (F > 50%), and is currently under evaluation in phase I clinical trials.

  DOI：

  10.1021/jm300281x
• 作为产物：
  描述：

  2-溴-1-间甲苯-乙酮 在 calcium sulfate 、 水 、 silver(l) oxide 作用下， 以 乙腈 为溶剂， 生成 2-[(2-propenyloxy)]-1-(3-methylphenyl)ethanone
  参考文献：
  名称：

  Identification of a 4-(Hydroxymethyl)diarylhydantoin as a Selective Androgen Receptor Modulator

  摘要：

  Structural modification performed on a 4-methyl-4-(4-hydroxyphenyphyl)hydantoin series is described which resulted in the development of a new series of 4-(hydroxymethyl)diarylhydantoin analogues as potent, partial agonists of the human androgen receptor. This led to the identification of (S)-(-)-4-(4-(hydroxymethyl)-3-methyl-2,5-dioxo-4-phenylimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile ((S)-(-)-18a, GLPG0492) evaluated in vivo in a classical model of orchidectomized rat. In this model, (-)-18a exhibited anabolic activity on muscle, strongly dissociated from the androgenic activity on prostate after oral dosing. (-)-18a has very good pharmacokinetic properties, including bioavailability in rat (F > 50%), and is currently under evaluation in phase I clinical trials.

  DOI：

  10.1021/jm300281x

文献信息

• Identification of a 4-(Hydroxymethyl)diarylhydantoin as a Selective Androgen Receptor Modulator
  作者：François Nique、Séverine Hebbe、Nicolas Triballeau、Christophe Peixoto、Jean-Michel Lefrançois、Hélène Jary、Luke Alvey、Murielle Manioc、Christopher Housseman、Hugo Klaassen、Kris Van Beeck、Denis Guédin、Florence Namour、Dominque Minet、Ellen Van der Aar、Jean Feyen、Stephen Fletcher、Roland Blanqué、Catherine Robin-Jagerschmidt、Pierre Deprez

  DOI：10.1021/jm300281x

  日期：2012.10.11

  Structural modification performed on a 4-methyl-4-(4-hydroxyphenyphyl)hydantoin series is described which resulted in the development of a new series of 4-(hydroxymethyl)diarylhydantoin analogues as potent, partial agonists of the human androgen receptor. This led to the identification of (S)-(-)-4-(4-(hydroxymethyl)-3-methyl-2,5-dioxo-4-phenylimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile ((S)-(-)-18a, GLPG0492) evaluated in vivo in a classical model of orchidectomized rat. In this model, (-)-18a exhibited anabolic activity on muscle, strongly dissociated from the androgenic activity on prostate after oral dosing. (-)-18a has very good pharmacokinetic properties, including bioavailability in rat (F > 50%), and is currently under evaluation in phase I clinical trials.