4-(2-oxo-cyclohexyl)-2-trifluoromethyl-benzonitrile | 1076225-16-5

• 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: 4-(2-oxo-cyclohexyl)-2-trifluoromethyl-benzonitrile
• 英文别名: 4-(2-Oxocyclohexyl)-2-(trifluoromethyl)benzonitrile
• CAS: 1076225-16-5
• 化学式: C₁₄H₁₂F₃NO
• 分子量: 267.251
• InChiKey: ICQBQJIUTRFYGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2-oxo-cyclohexyl)-2-trifluoromethyl-benzonitrile 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以31%的产率得到4-(2-hydroxy-cyclohexyl)-2-trifluoromethyl-benzonitrile
  参考文献：
  名称：

  Rational Design and Synthesis of 4-((1R,2R)-2-Hydroxycyclohexyl)-2(trifluoromethyl)benzonitrile (PF-998425), a Novel, Nonsteroidal Androgen Receptor Antagonist Devoid of Phototoxicity for Dermatological Indications

  摘要：

  4-((1R,2R)-2-Hydroxycyclohexyl)-2(trifluoromethyl)benzonitrile [PF-0998425, (-)-6a] is a novel, nonsteroidal androgen receptor antagonist for sebum control and treatment of androgenetic alopecia. It is potent, selective, and active in vivo. The compound is rapidly metabolized systemically, thereby reducing the risk of unwanted systemic side effects due to its primary pharmacology. (-)-6a was tested negative in the 3T3 NRU assay, validating our rationale that reduction of conjugation might reduce potential phototoxicity.

  DOI：

  10.1021/jm8009316
• 作为产物：
  描述：

  环己酮 、 4-氟-2-(三氟甲基)苯甲腈 在 sodium hydride 作用下， 以 乙二醇二甲醚 、 mineral oil 为溶剂， 反应 1.08h， 以31%的产率得到4-(2-oxo-cyclohexyl)-2-trifluoromethyl-benzonitrile
  参考文献：
  名称：

  Rational Design and Synthesis of 4-((1R,2R)-2-Hydroxycyclohexyl)-2(trifluoromethyl)benzonitrile (PF-998425), a Novel, Nonsteroidal Androgen Receptor Antagonist Devoid of Phototoxicity for Dermatological Indications

  摘要：

  4-((1R,2R)-2-Hydroxycyclohexyl)-2(trifluoromethyl)benzonitrile [PF-0998425, (-)-6a] is a novel, nonsteroidal androgen receptor antagonist for sebum control and treatment of androgenetic alopecia. It is potent, selective, and active in vivo. The compound is rapidly metabolized systemically, thereby reducing the risk of unwanted systemic side effects due to its primary pharmacology. (-)-6a was tested negative in the 3T3 NRU assay, validating our rationale that reduction of conjugation might reduce potential phototoxicity.

  DOI：

  10.1021/jm8009316