3,4-dihydro-5,6-O-isopropylidene antirrhinoside | 196859-85-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-dihydro-5,6-O-isopropylidene antirrhinoside
• CAS: 196859-85-5
• 化学式: C₁₈H₂₈O₁₀
• 分子量: 404.414
• InChiKey: IGZNQCOGLZYQON-PRCDFJNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.77
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  139.6
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-5,6-O-isopropylidene antirrhinoside 在 sodium tetrahydroborate 、 β-glucosidase 作用下， 以 甲醇 、 水 为溶剂， 反应 76.0h， 生成 2-((1aS,1bR,4aS,5R,5aR)-5-Hydroxymethyl-3,3,5a-trimethyl-tetrahydro-1,2,4-trioxa-cyclopropa[a]pentalen-4a-yl)-ethanol
  参考文献：
  名称：

  Synthesis of Monoterpene Piperidines from the Iridoid Glucoside Antirrhinoside

  摘要：

  Synthesis of five novel piperidine monoterpene alkaloids (17-21) using the iridoid glucoside antirrhinoside (4) as a synthon is described. Two strategies for their preparation were investigated: the first possible pathway involved an intermediate diol, 13, from which the piperidine ring was expected to be constructed via reaction of its ditosylate with an amine; the second strategy involved a double reductive amination as the key step to the piperidine ring, which proved successful. The stereochemistry of C-5 and C-9 in the obtained piperidine monoterpenes was the same as that reported for alpha-skytanthine (3), a known isolate from Skytanthus acutus (Apocynaceae).

  DOI：

  10.1021/np9702648
• 作为产物：
  描述：

  5,6-O-isopropylidene antirrhinoside 在 platinum on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以93%的产率得到3,4-dihydro-5,6-O-isopropylidene antirrhinoside
  参考文献：
  名称：

  Synthesis of Monoterpene Piperidines from the Iridoid Glucoside Antirrhinoside

  摘要：

  Synthesis of five novel piperidine monoterpene alkaloids (17-21) using the iridoid glucoside antirrhinoside (4) as a synthon is described. Two strategies for their preparation were investigated: the first possible pathway involved an intermediate diol, 13, from which the piperidine ring was expected to be constructed via reaction of its ditosylate with an amine; the second strategy involved a double reductive amination as the key step to the piperidine ring, which proved successful. The stereochemistry of C-5 and C-9 in the obtained piperidine monoterpenes was the same as that reported for alpha-skytanthine (3), a known isolate from Skytanthus acutus (Apocynaceae).

  DOI：

  10.1021/np9702648