(1S,3R,5R)-3-{3-[4-(2-Methyl-imidazol-1-yl)-phenylsulfanyl]-phenyl}-8-oxa-bicyclo[3.2.1]octane-3-carbonitrile | 189277-92-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (1S,3R,5R)-3-{3-[4-(2-Methyl-imidazol-1-yl)-phenylsulfanyl]-phenyl}-8-oxa-bicyclo[3.2.1]octane-3-carbonitrile
• CAS: 189277-92-7
• 化学式: C₂₄H₂₃N₃OS
• 分子量: 401.532
• InChiKey: ZDFSCQXPBSOZPW-RUMRUAAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.84
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1S,3R,5R)-3-{3-[4-(2-Methyl-imidazol-1-yl)-phenylsulfanyl]-phenyl}-8-oxa-bicyclo[3.2.1]octane-3-carbonitrile 在 氢氧化钾 、 叔丁醇 作用下， 反应 4.0h， 以70%的产率得到
  参考文献：
  名称：

  5-Lipoxygenase inhibitors: convenient synthesis of 4-[3-(4-heterocyclylphenylthio)phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-carboxamide analogues

  摘要：

  A convenient synthetic route to 4-[3-(4-heterocyclylphenylthio)phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-earboxamide analogues as 5-LO inhibitors is described. This methodology enabled rapid development of structure-activity relationships (SARs) leading to improvement of pharmacological properties. Thus, new compounds with higher 5-LO inhibitory potency were discovered. The stereo-chemistry requirements of the tetrahydropyran ring are also discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.041
• 作为产物：
  描述：

  3-碘苯乙腈 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 0.25h， 生成 (1S,3R,5R)-3-{3-[4-(2-Methyl-imidazol-1-yl)-phenylsulfanyl]-phenyl}-8-oxa-bicyclo[3.2.1]octane-3-carbonitrile
  参考文献：
  名称：

  5-Lipoxygenase inhibitors: convenient synthesis of 4-[3-(4-heterocyclylphenylthio)phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-carboxamide analogues

  摘要：

  A convenient synthetic route to 4-[3-(4-heterocyclylphenylthio)phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-earboxamide analogues as 5-LO inhibitors is described. This methodology enabled rapid development of structure-activity relationships (SARs) leading to improvement of pharmacological properties. Thus, new compounds with higher 5-LO inhibitory potency were discovered. The stereo-chemistry requirements of the tetrahydropyran ring are also discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.041