叶含龙头花甙 | 20770-65-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 叶含龙头花甙
• 英文名称: anthirrinoside
• 英文别名: antirrhinoside；(2S,3R,4S,5S,6R)-2-[[(1S,2R,4S,5R,6S,10S)-5,6-dihydroxy-2-methyl-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-10-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 20770-65-4
• 化学式: C₁₅H₂₂O₁₀
• 分子量: 362.334
• InChiKey: UBAIOTDKPLIEDD-RNCITLLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  162
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  叶含龙头花甙 在 platinum on activated charcoal sodium tetrahydroborate 、 氢气 、 4-甲基苯磺酸吡啶 、 溶剂黄146 、 β-glucosidase 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 丙酮 为溶剂， 15.0~60.0 ℃ 、101.33 kPa 条件下， 反应 81.0h， 生成 (1S,5R,6S,7S,11R)-11-Hydroxymethyl-3,3,7-trimethyl-2,4,8-trioxa-tricyclo[5.3.1.0^1,5]undecan-6-ol
  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

文献信息

• Ozonolysis of Protected Iridoid Glucosides
  作者：Henrik Franzyk、Jon Holbech Rasmussen、Søren Rosendal Jensen

  DOI：10.1002/(sici)1099-0690(199802)1998:2<365::aid-ejoc365>3.0.co;2-z

  日期：1998.2
• Synthesis of Monoterpene Piperidines from the Iridoid Glucoside Antirrhinoside
  作者：Henrik Franzyk、Signe M. Frederiksen、Søren Rosendal Jensen

  DOI：10.1021/np9702648

  日期：1997.10.1

  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).