piperodione | 1427509-86-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: piperodione
• 英文别名: Piperodione；5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpentane-1,2,5-trione
• CAS: 1427509-86-1
• 化学式: C₁₇H₁₉NO₅
• 分子量: 317.342
• InChiKey: CNJOJYZDMBPQTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-亚甲二氧苯乙酮 在 3-苄基羟乙基甲基噻唑氯化锂 、 三乙胺 、 三氟乙酸 、 diisopropylammonium trifluoroacetate 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 piperodione
  参考文献：
  名称：

  First total synthesis of piperodione and analogs

  摘要：

  Piperodione (3), a secondary metabolite previously isolated from the Javanese pepper plant Piper retrofractum in 0.0002% isolated yield was synthesized in a convergent strategy utilizing a Mannich and a Stetter reaction. An over-all yield of 76% could be achieved. Several analogs were prepared by this synthetic sequence. None of the compounds showed a significant cytotoxicity for human tumor cells (photometric sulforhodamine B assay). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.079

文献信息

• First total synthesis of piperodione and analogs
  作者：Sven Sommerwerk、Simone Kern、Lucie Heller、René Csuk

  DOI：10.1016/j.tetlet.2014.09.079

  日期：2014.11

  Piperodione (3), a secondary metabolite previously isolated from the Javanese pepper plant Piper retrofractum in 0.0002% isolated yield was synthesized in a convergent strategy utilizing a Mannich and a Stetter reaction. An over-all yield of 76% could be achieved. Several analogs were prepared by this synthetic sequence. None of the compounds showed a significant cytotoxicity for human tumor cells (photometric sulforhodamine B assay). (C) 2014 Elsevier Ltd. All rights reserved.