(2S,3S)-1,4-dioxo-1,4-di-1-piperidinyl-2,3-butanediol | 111606-71-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (2S,3S)-1,4-dioxo-1,4-di-1-piperidinyl-2,3-butanediol
• 英文别名: 1,1'-tartaroyl-di-piperidine, (d-tartaric acid )-dipiperidide；1,1'-Tartaroyl-di-piperidin, (d-Weinsaeure)-dipiperidid；(-)-D-tartaric acid bis-(N-piperidinamide)；(2S,3S)-2,3-dihydroxy-1,4-di(piperidin-1-yl)butane-1,4-dione
• CAS: 111606-71-4
• 化学式: C₁₄H₂₄N₂O₄
• 分子量: 284.356
• InChiKey: DGAQUUWVTUIQEO-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  81.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S)-1,4-dioxo-1,4-di-1-piperidinyl-2,3-butanediol 在 3-苄基羟乙基甲基噻唑氯化锂 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.5h， 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
• 作为产物：
  描述：

  哌啶 、 L-(+)-酒石酸二乙酯 生成 (2S,3S)-1,4-dioxo-1,4-di-1-piperidinyl-2,3-butanediol
  参考文献：
  名称：

  Frankland; Ormerod, Journal of the Chemical Society, 1903, vol. 83, p. 1348

  摘要：

  DOI：

文献信息

• GIORDANO, CLAUDIO;CASTALDI, GRAZIANO, J. ORG. CHEM., 54,(1989) N, C. 1470-1473
  作者：GIORDANO, CLAUDIO、CASTALDI, GRAZIANO

  DOI：——

  日期：——
• 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.
• Frankland; Ormerod, Journal of the Chemical Society, 1903, vol. 83, p. 1348
  作者：Frankland、Ormerod

  DOI：——

  日期：——