4-[3-(4-Pyrrol-1-ylmethyl-phenylsulfanyl)-phenyl]-tetrahydro-pyran-4-carboxylic acid methyl ester | 854750-60-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-[3-(4-Pyrrol-1-ylmethyl-phenylsulfanyl)-phenyl]-tetrahydro-pyran-4-carboxylic acid methyl ester
• CAS: 854750-60-0
• 化学式: C₂₄H₂₅NO₃S
• 分子量: 407.533
• InChiKey: SENHZANALOMALZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  40.46
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-[3-(4-Pyrrol-1-ylmethyl-phenylsulfanyl)-phenyl]-tetrahydro-pyran-4-carboxylic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 以100%的产率得到4-[3-[4-(pyrrol-1-ylmethyl)phenylthio]phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-carboxylic acid
  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：

  methyl 4-(3-mercaptophenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate 、 1-[(4-碘苯基)甲基]吡咯 在 四(三苯基膦)钯 、 sodium t-butanolate 作用下， 以 乙醇 为溶剂， 以54%的产率得到4-[3-(4-Pyrrol-1-ylmethyl-phenylsulfanyl)-phenyl]-tetrahydro-pyran-4-carboxylic acid methyl ester
  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