ethyl 4-(3-(phenylthio)propyl)-6,7-dihydro-5H-cyclopenta[c]pyridine-1-carboxylate | 1028832-46-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: ethyl 4-(3-(phenylthio)propyl)-6,7-dihydro-5H-cyclopenta[c]pyridine-1-carboxylate
• 英文别名: ethyl 4-(3-phenylsulfanylpropyl)-6,7-dihydro-5H-cyclopenta[c]pyridine-1-carboxylate
• CAS: 1028832-46-3
• 化学式: C₂₀H₂₃NO₂S
• 分子量: 341.474
• InChiKey: GFZPDVSRBONQOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-(3-(phenylthio)propyl)-6,7-dihydro-5H-cyclopenta[c]pyridine-1-carboxylate 在 二异丁基氢化铝 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 2.5h， 以89%的产率得到4-(3-(phenylthio)propyl)-6,7-dihydro-5H-cyclopenta[c]pyridine-1-carboxaldehyde
  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：

  3-ethoxycarbonyl-5-(3-phenylthiopropyl)-1,2,4-triazine 、 环戊酮 在 四氢吡咯 、 silica gel 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 28.0h， 以89%的产率得到ethyl 4-(3-(phenylthio)propyl)-6,7-dihydro-5H-cyclopenta[c]pyridine-1-carboxylate
  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

• An efficient 1,2,4-triazine-based route to the louisianin alkaloids
  作者：Nicola Catozzi、Pierre Wasnaire、Richard J.K. Taylor

  DOI：10.1016/j.tetlet.2008.03.026

  日期：2008.4

  A new, short and efficient route to louisianins C and D is described in which the pyridine ring is constructed from a disubstituted 1,2,4-triazine by an inverse-electron-demand Diels-Alder/retro-Diels-Alder/aromatisation cascade sequence. This eight-step route produces louisianin C in 16% overall yield from the commercially available 5-chloropent-1-yne. (c) 2008 Elsevier Ltd. All rights reserved.
• 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.