(R)-(+)-3-hydroxy-4,4-dimethyl-1-(4-methyl-sulfanyl-benzyl)pyrrolidin-2-one | 1227380-64-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (R)-(+)-3-hydroxy-4,4-dimethyl-1-(4-methyl-sulfanyl-benzyl)pyrrolidin-2-one
• 英文别名: (3R)-3-hydroxy-4,4-dimethyl-1-[(4-methylsulfanylphenyl)methyl]pyrrolidin-2-one
• CAS: 1227380-64-4
• 化学式: C₁₄H₁₉NO₂S
• 分子量: 265.376
• InChiKey: YRTFKUDVXAIOJN-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(+)-3-hydroxy-4,4-dimethyl-1-(4-methyl-sulfanyl-benzyl)pyrrolidin-2-one 、 4-氟-2-(三氟甲基)苯甲腈 在 potassium phosphate 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以95%的产率得到(R)-(+)-4-[4,4-dimethyl-1-(4-methylsulfanyl-benzyl)-2-oxo-pyrrolidin-3-yloxy]-2-trifluoromethyl-benzonitrile
  参考文献：
  名称：

  Rational Design of a Topical Androgen Receptor Antagonist for the Suppression of Sebum Production with Properties Suitable for Follicular Delivery

  摘要：

  A novel nonsteroidal androgen receptor antagonist, (R)-4-(1-benzy1-4,4-dimethyl-2-oxopyrrolidin-3-yloxy)2-(trifluoromethyl)benzonitrile (1), for the topical control of sebum production is reported. This compound, which is potent, selective, and efficacious in the clinically validated golden Syrian hamster ear animal model, was designed to be delivered to the pilosebaceous unit, the site of action, preferentially by the follicular route.

  DOI：

  10.1021/jm9018004
• 作为产物：
  描述：

  (R)-(+)-2,4-dihydroxy-3,3-dimethyl-N-(4-methyl-sulfanyl-benzyl)butyramide 在 甲基磺酰氯 、 三乙胺 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到(R)-(+)-3-hydroxy-4,4-dimethyl-1-(4-methyl-sulfanyl-benzyl)pyrrolidin-2-one
  参考文献：
  名称：

  Rational Design of a Topical Androgen Receptor Antagonist for the Suppression of Sebum Production with Properties Suitable for Follicular Delivery

  摘要：

  A novel nonsteroidal androgen receptor antagonist, (R)-4-(1-benzy1-4,4-dimethyl-2-oxopyrrolidin-3-yloxy)2-(trifluoromethyl)benzonitrile (1), for the topical control of sebum production is reported. This compound, which is potent, selective, and efficacious in the clinically validated golden Syrian hamster ear animal model, was designed to be delivered to the pilosebaceous unit, the site of action, preferentially by the follicular route.

  DOI：

  10.1021/jm9018004