1-chloro-4-(3-(phenylthio)propyl)-6,7-dihydro-5H-cyclopenta[c]pyridine | 1192046-94-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-chloro-4-(3-(phenylthio)propyl)-6,7-dihydro-5H-cyclopenta[c]pyridine
• 英文别名: 1-chloro-4-(3-phenylsulfanylpropyl)-6,7-dihydro-5H-cyclopenta[c]pyridine
• CAS: 1192046-94-8
• 化学式: C₁₇H₁₈ClNS
• 分子量: 303.856
• InChiKey: VRNPBWABAZLFSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-chloro-4-(3-(phenylthio)propyl)-6,7-dihydro-5H-cyclopenta[c]pyridine 在 lithium hexamethyldisilazane 、 亚磷酸三乙酯 、 氧气 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 以86%的产率得到1-chloro-4-(3-(phenylthio)propyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-5-ol
  参考文献：
  名称：

  Synthesis of the Louisianin Alkaloid Family via a 1,2,4-Triazine Inverse-Electron-Demand Diels−Alder Approach

  摘要：

  Isolated in 1995, the four members of the louisianin family (A, B, C and D) are simple pyridine and 2-pyridone alkaloids that display both antibacterial and anticancer activity. Herein we describe the synthesis of all four members of the louisianin family, from I conveniently prepared 1,2,4-triazine and via I common tetrasubstituted pyridine intermediate. This study includes the synthesis of louisianin B in both racemic form and is the (-)-enantiomer.

  DOI：

  10.1021/jo901761r
• 作为产物：
  描述：

  4-(3-(phenylthio)propyl)-6,7-dihydro-5H-cyclopenta[c]pyridine-1-carboxylic acid 在 四氯化碳 、 1-氧化-2-巯基吡啶 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 反应 14.0h， 以56%的产率得到1-chloro-4-(3-(phenylthio)propyl)-6,7-dihydro-5H-cyclopenta[c]pyridine
  参考文献：
  名称：

  Synthesis of the Louisianin Alkaloid Family via a 1,2,4-Triazine Inverse-Electron-Demand Diels−Alder Approach

  摘要：

  Isolated in 1995, the four members of the louisianin family (A, B, C and D) are simple pyridine and 2-pyridone alkaloids that display both antibacterial and anticancer activity. Herein we describe the synthesis of all four members of the louisianin family, from I conveniently prepared 1,2,4-triazine and via I common tetrasubstituted pyridine intermediate. This study includes the synthesis of louisianin B in both racemic form and is the (-)-enantiomer.

  DOI：

  10.1021/jo901761r

文献信息

• Synthesis of the Louisianin Alkaloid Family via a 1,2,4-Triazine Inverse-Electron-Demand Diels−Alder Approach
  作者：Nicola Catozzi、Michael G. Edwards、Steven A. Raw、Pierre Wasnaire、Richard J. K. Taylor

  DOI：10.1021/jo901761r

  日期：2009.11.6

  Isolated in 1995, the four members of the louisianin family (A, B, C and D) are simple pyridine and 2-pyridone alkaloids that display both antibacterial and anticancer activity. Herein we describe the synthesis of all four members of the louisianin family, from I conveniently prepared 1,2,4-triazine and via I common tetrasubstituted pyridine intermediate. This study includes the synthesis of louisianin B in both racemic form and is the (-)-enantiomer.