4-(3-Cyclopentyloxy-4-methoxy-phenyl)-cyclohexanone | 202718-69-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(3-Cyclopentyloxy-4-methoxy-phenyl)-cyclohexanone
• 英文别名: 4-(3-Cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one
• CAS: 202718-69-2
• 化学式: C₁₈H₂₄O₃
• 分子量: 288.387
• InChiKey: LPZMRVKAJJEVKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3-Cyclopentyloxy-4-methoxy-phenyl)-cyclohexanone 在 sodium hydroxide 、 正丁基锂 、 双氧水 、 三氟乙酸 作用下， 反应 0.75h， 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 氨 、 sodium 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.2h， 生成 4-(3-Cyclopentyloxy-4-methoxy-phenyl)-cyclohexanone
  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

文献信息

• 1,4-Cyclohexanecarboxylates:  Potent and Selective Inhibitors of Phosophodiesterase 4 for the Treatment of Asthma
  作者：Siegfried B. Christensen、Aimee Guider、Cornelia J. Forster、John G. Gleason、Paul E. Bender、Joseph M. Karpinski、Walter E. DeWolf,、Mary S. Barnette、David C. Underwood、Don E. Griswold、Lenora B. Cieslinski、Miriam Burman、Steven Bochnowicz、Ruth R. Osborn、Carol D. Manning、Marilyn Grous、Leonard M. Hillegas、Joan O'Leary Bartus、M. Dominic Ryan、Drake S. Eggleston、R. Curtis Haltiwanger、Theodore J. Torphy

  DOI：10.1021/jm970090r

  日期：1998.3.1

  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.