2-{4-[(R)-1-(5-Cyclopentyloxy-2-iodo-4-methoxy-phenyl)-2-pyridin-4-yl-ethyl]-phenyl}-1,1,1,3,3,3-hexafluoro-propan-2-ol | 499120-87-5

• 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-{4-[(R)-1-(5-Cyclopentyloxy-2-iodo-4-methoxy-phenyl)-2-pyridin-4-yl-ethyl]-phenyl}-1,1,1,3,3,3-hexafluoro-propan-2-ol
• CAS: 499120-87-5
• 化学式: C₂₈H₂₆F₆INO₃
• 分子量: 665.414
• InChiKey: YWGQXIUWBPLLEE-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  39.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  51.58
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-{4-[(R)-1-(5-Cyclopentyloxy-2-iodo-4-methoxy-phenyl)-2-pyridin-4-yl-ethyl]-phenyl}-1,1,1,3,3,3-hexafluoro-propan-2-ol 在 10% palladium on active carbon 氢气 、 三乙胺 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成 2-[4-[(1R)-1-(5-cyclopentyloxy-4-methoxy-2-tritiophenyl)-2-pyridin-4-ylethyl]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol
  参考文献：
  名称：

  Improving metabolic stability of phosphodiesterase-4 inhibitors containing a substituted catechol: prevention of reactive intermediate formation and covalent binding

  摘要：

  A detailed study directed towards metabolic stability optimization of the alkoxy substituents on the catechol moiety of CDP-840 is reported. Replacement of the methoxy and cyclopentyloxy substituents by cyclobutyloxy and/or difluromethoxy groups resulted in the discovery of potent and selective PDE4 inhibitors where the formation of reactive metabolites that could covalently bind to microsomal protein was significantly reduced or eliminated. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00349-9
• 作为产物：
  描述：

  (R)-3-(3-Cyclopentyloxy-4-methoxy-phenyl)-2-pyridin-4-yl-3-{4-[2,2,2-trifluoro-1-trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-phenyl}-thiopropionic acid S-propyl ester 在 lithium hydroxide 、 N-碘代丁二酰亚胺 、 四丁基氟化铵 、 三氟乙酸 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 生成 2-{4-[(R)-1-(5-Cyclopentyloxy-2-iodo-4-methoxy-phenyl)-2-pyridin-4-yl-ethyl]-phenyl}-1,1,1,3,3,3-hexafluoro-propan-2-ol
  参考文献：
  名称：

  Improving metabolic stability of phosphodiesterase-4 inhibitors containing a substituted catechol: prevention of reactive intermediate formation and covalent binding

  摘要：

  A detailed study directed towards metabolic stability optimization of the alkoxy substituents on the catechol moiety of CDP-840 is reported. Replacement of the methoxy and cyclopentyloxy substituents by cyclobutyloxy and/or difluromethoxy groups resulted in the discovery of potent and selective PDE4 inhibitors where the formation of reactive metabolites that could covalently bind to microsomal protein was significantly reduced or eliminated. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00349-9