4-[(Z)-2-(3-cyclopentyloxy-4-methoxyphenyl)-2-phenylethenyl]pyridine | 162543-82-0

• 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-[(Z)-2-(3-cyclopentyloxy-4-methoxyphenyl)-2-phenylethenyl]pyridine
• CAS: 162543-82-0
• 化学式: C₂₅H₂₅NO₂
• 分子量: 371.479
• InChiKey: HVDREXZQOJJRAC-QJOMJCCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(Z)-2-(3-cyclopentyloxy-4-methoxyphenyl)-2-phenylethenyl]pyridine 在 sodium hydroxide 、 sodium hypochlorite 、 锂硼氢 、 硼烷四氢呋喃络合物 、 S,S salen Mn(III) 、 4-(3-苯基丙基)吡啶1-氧化物 作用下， 生成 、 (1S,2S)-2-(3-cyclopentyloxy-4-methoxyphenyl)-2-phenyl-1-pyridin-4-ylethanol
  参考文献：
  名称：

  Asymmetric Synthesis of CDP840 by Jacobsen Epoxidation. An Unusual Syn Selective Reduction of an Epoxide

  摘要：

  An asymmetric synthesis of the PDE IV inhibitor, CDP840 (3) is reported. The absolute stereochemistry was controlled by a Jacobsen epoxidation of the Z triaryl olefin 8 (89% ee) or the E triaryl olefin 9 (48% ee). The disparate results in stereocontrol were interpreted in terms of the "skewed side-on approach model" proposed by Jacobsen. LiBK4 . BH3 reduction of the epoxides was found to proceed with retention of configuration.

  DOI：

  10.1021/jo971476c
• 作为产物：
  描述：

  3-环戊氧-4-甲氧基苯甲醛 在 叔丁基过氧化氢 、 ruthenium trichloride 、 甲烷磺酸 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 8.5h， 生成 4-[(Z)-2-(3-cyclopentyloxy-4-methoxyphenyl)-2-phenylethenyl]pyridine
  参考文献：
  名称：

  Asymmetric Synthesis of CDP840 by Jacobsen Epoxidation. An Unusual Syn Selective Reduction of an Epoxide

  摘要：

  An asymmetric synthesis of the PDE IV inhibitor, CDP840 (3) is reported. The absolute stereochemistry was controlled by a Jacobsen epoxidation of the Z triaryl olefin 8 (89% ee) or the E triaryl olefin 9 (48% ee). The disparate results in stereocontrol were interpreted in terms of the "skewed side-on approach model" proposed by Jacobsen. LiBK4 . BH3 reduction of the epoxides was found to proceed with retention of configuration.

  DOI：

  10.1021/jo971476c

文献信息

• Asymmetric Synthesis of CDP840 by Jacobsen Epoxidation. An Unusual Syn Selective Reduction of an Epoxide
  作者：J. E. Lynch、W.-B. Choi、H. R. O. Churchill、R. P. Volante、R. A. Reamer、R. G. Ball

  DOI：10.1021/jo971476c

  日期：1997.12.1

  An asymmetric synthesis of the PDE IV inhibitor, CDP840 (3) is reported. The absolute stereochemistry was controlled by a Jacobsen epoxidation of the Z triaryl olefin 8 (89% ee) or the E triaryl olefin 9 (48% ee). The disparate results in stereocontrol were interpreted in terms of the "skewed side-on approach model" proposed by Jacobsen. LiBK4 . BH3 reduction of the epoxides was found to proceed with retention of configuration.