2-[4-(3-Cyclopentyloxy-4-methoxy-phenyl)-cyclohexylidene]-[1,3]dithiane | 202718-70-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[4-(3-Cyclopentyloxy-4-methoxy-phenyl)-cyclohexylidene]-[1,3]dithiane
• 英文别名: 2-[4-(3-Cyclopentyloxy-4-methoxyphenyl)cyclohexylidene]-1,3-dithiane
• CAS: 202718-70-5
• 化学式: C₂₂H₃₀O₂S₂
• 分子量: 390.611
• InChiKey: LQBRFGRIZRRPRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  69.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[4-(3-Cyclopentyloxy-4-methoxy-phenyl)-cyclohexylidene]-[1,3]dithiane 在 sodium hydroxide 、 双氧水 、 三氟乙酸 作用下， 生成 4-(3-Cyclopentyloxy-4-methoxy-phenyl)-cyclohexanecarboxylic acid
  参考文献：
  名称：

  1,4-Cyclohexanecarboxylates:  Potent and Selective Inhibitors of Phosophodiesterase 4 for the Treatment of Asthma

  摘要：

  Evaluation of a variety of PDE4 inhibitors in a series of cellular and in vivo assays suggested a strategy to improve the therapeutic index of PDE4 inhibitors by increasing their selectivity for the ability to inhibit PDE4 catalytic activity versus the ability to compete for high affinity [H-3]rolipram-binding sites in the central nervous system. Use of this strategy led ultimately to the identification of cis-4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexane-1 -carboxylic acid (1, SB 207499, Ariflo(TM)), a potent second-generation inhibitor of PDE4 with a decreased potential for side effects versus the archetypic first generation inhibitor, (R)-rolipram.

  DOI：

  10.1021/jm970090r
• 作为产物：
  描述：

  1-[3-(环戊基氧基)-4-甲氧基苯基]-4-氧代环己烷甲腈 在 正丁基锂 、 氨 、 sodium 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.95h， 生成 2-[4-(3-Cyclopentyloxy-4-methoxy-phenyl)-cyclohexylidene]-[1,3]dithiane
  参考文献：
  名称：

  1,4-Cyclohexanecarboxylates:  Potent and Selective Inhibitors of Phosophodiesterase 4 for the Treatment of Asthma

  摘要：

  Evaluation of a variety of PDE4 inhibitors in a series of cellular and in vivo assays suggested a strategy to improve the therapeutic index of PDE4 inhibitors by increasing their selectivity for the ability to inhibit PDE4 catalytic activity versus the ability to compete for high affinity [H-3]rolipram-binding sites in the central nervous system. Use of this strategy led ultimately to the identification of cis-4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexane-1 -carboxylic acid (1, SB 207499, Ariflo(TM)), a potent second-generation inhibitor of PDE4 with a decreased potential for side effects versus the archetypic first generation inhibitor, (R)-rolipram.

  DOI：

  10.1021/jm970090r