5H-环戊二烯并[c]吡啶-5-酮,6,7-二氢-4-(2-丙烯-1-基)- | 171784-05-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5H-环戊二烯并[c]吡啶-5-酮,6,7-二氢-4-(2-丙烯-1-基)-
• 英文名称: 6,7-dihydro-4-(2-propenyl)-5H-cyclopenta[c]pyridin-5-one
• 英文别名: 4-allyl-6,7-dihydro-5H-cyclopenta[c]pyridin-5-one；louisianin C；4-prop-2-enyl-6,7-dihydrocyclopenta[c]pyridin-5-one
• CAS: 171784-05-7
• 化学式: C₁₁H₁₁NO
• 分子量: 173.214
• InChiKey: LTBYIQKSNDZSNC-UHFFFAOYSA-N

物化性质

• 沸点：
  327.2±21.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5H-环戊二烯并[c]吡啶-5-酮,6,7-二氢-4-(2-丙烯-1-基)- 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 苯 为溶剂， 反应 1.0h， 以84%的产率得到Louisianin D
  参考文献：
  名称：

  Efficient Chemical Conversion of Louisianin A to C and D, The Inhibitor of Angiogenesis.

  摘要：

  DOI：

  10.7164/antibiotics.50.274
• 作为产物：
  描述：

  3,5-二溴吡啶 在 吡啶 、 chromium(VI) oxide 、 bis-triphenylphosphine-palladium(II) chloride 、 三氟化硼乙醚 、 9-硼双环[3.3.1]壬烷 、 四丁基二氟三苯硅酸铵 、 lithium diisopropyl amide 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 正己烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 40.0h， 生成 5H-环戊二烯并[c]吡啶-5-酮,6,7-二氢-4-(2-丙烯-1-基)-
  参考文献：
  名称：

  Synthesis of Louisianin C

  摘要：

  The synthesis of louisianin C (3), a member of a small family of 3,4,5-trisubstituted pyridyl natural products, is achieved in six steps and 11% overall yield starting from commercially available 3,5-dibromopyridine. The key step is a fluoride-induced desilylation-cyclization to afford carbinol 12.

  DOI：

  10.1021/jo0341618

文献信息

• Efficient total syntheses of louisianins C and D
  作者：Ching-Yao Chang、Hui-Ming Liu、Ru-Ting Hsu

  DOI：10.1016/j.tet.2008.11.075

  日期：2009.1

  An efficient synthetic route for the preparation of louisianins C and D was developed starting with the commercially available 4-cyanopyridine. Louisianins C and D were synthesized in seven steps and with overall yields 22% and 20%, respectively, following a novel cyclization-decarboxylation sequence involving 4-bromo-6,7-dihydrocyclopenta[c]pyridin-5-one as the key intermediate. (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.
• 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.
• Efficient Chemical Conversion of Louisianin A to C and D, The Inhibitor of Angiogenesis.
  作者：TOSHIAKI SUNAZUKA、TIAN ZHI-MING、YOSHIHIRO HARIGAYA、SATOSHI TAKAMATSU、MASAHIKO HAYASHI、KANKI KOMIYAMA、SATOSHI OMURA

  DOI：10.7164/antibiotics.50.274

  日期：——
• Synthesis of Louisianin C
  作者：John M. Beierle、Ekundayo B. Osimboni、Costa Metallinos、Yajun Zhao、T. Ross Kelly

  DOI：10.1021/jo0341618

  日期：2003.6.1

  The synthesis of louisianin C (3), a member of a small family of 3,4,5-trisubstituted pyridyl natural products, is achieved in six steps and 11% overall yield starting from commercially available 3,5-dibromopyridine. The key step is a fluoride-induced desilylation-cyclization to afford carbinol 12.