rel-1,1-Dimethylethyl (2R,3R)-3-(acetyloxy)-2-(2-propen-1-yl)-1-piperidinecarboxylate | 616890-34-7

• 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: rel-1,1-Dimethylethyl (2R,3R)-3-(acetyloxy)-2-(2-propen-1-yl)-1-piperidinecarboxylate
• 英文别名: tert-butyl (2S,3S)-3-acetyloxy-2-prop-2-enylpiperidine-1-carboxylate
• CAS: 616890-34-7
• 化学式: C₁₅H₂₅NO₄
• 分子量: 283.368
• InChiKey: IGGAJPOTNJBIGS-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  rel-1,1-Dimethylethyl (2R,3R)-3-(acetyloxy)-2-(2-propen-1-yl)-1-piperidinecarboxylate 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 10.0h， 生成 、
  参考文献：
  名称：

  Synthesis of febrifuginol analogues and evaluation of their biological activities

  摘要：

  A new series of febrifuginol analogues was prepared from L-glutamic acid. An antimalarial activity evaluation against chloroquine-sensitive (T96) and chloroquine-resistant (K1) Plasmodium falciparum indicated that all the tested compounds had very strong inhibitory activity. Compounds 4 and 17b' were inactive against KB, MCF7, HepG2 and LU1 cell lines even at a concentration of 100 mu M, while they exhibited significant inhibition towards P. falciparum. Comparison of the antimalarial activity and the cytotoxic properties revealed that the 2'S isomers were more active than the corresponding 2'R isomers for this series of febrifuginol analogues, indicating that the C-2' position is critical for the biological activity of this class of compounds. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.11.028
• 作为产物：
  描述：

  在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium azide 、 dimethyl sulfide borane 、 palladium on activated charcoal 、 三氟化硼乙醚 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 25.0h， 生成 rel-1,1-Dimethylethyl (2R,3R)-3-(acetyloxy)-2-(2-propen-1-yl)-1-piperidinecarboxylate
  参考文献：
  名称：

  Synthesis of febrifuginol analogues and evaluation of their biological activities

  摘要：

  A new series of febrifuginol analogues was prepared from L-glutamic acid. An antimalarial activity evaluation against chloroquine-sensitive (T96) and chloroquine-resistant (K1) Plasmodium falciparum indicated that all the tested compounds had very strong inhibitory activity. Compounds 4 and 17b' were inactive against KB, MCF7, HepG2 and LU1 cell lines even at a concentration of 100 mu M, while they exhibited significant inhibition towards P. falciparum. Comparison of the antimalarial activity and the cytotoxic properties revealed that the 2'S isomers were more active than the corresponding 2'R isomers for this series of febrifuginol analogues, indicating that the C-2' position is critical for the biological activity of this class of compounds. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.11.028