(+/-)-lycopoclavamine B | 1332832-51-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: (+/-)-lycopoclavamine B
• 英文别名: (1S,2R,4S,6S)-2,4-dihydroxy-4-methyl-13-azatetracyclo[7.7.0.01,6.02,13]hexadec-9-en-8-one
• CAS: 1332832-51-5
• 化学式: C₁₆H₂₃NO₃
• 分子量: 277.364
• InChiKey: NRCKHAVZPRFWJU-IPOQPSJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 水 、 碳酸氢钠 、 potassium carbonate 、 苯硫酚 、 三氟乙酸 、 potassium hydroxide 、 2-碘酰基苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 、 乙腈 为溶剂， 反应 32.0h， 生成 (+/-)-lycopoclavamine B
  参考文献：
  名称：

  Syntheses of (±)-Serratine, (±)-Lycoposerramine T, and (±)-Lycopoclavamine B

  摘要：

  The first total syntheses of (+/-)-serratine, (+/-)-lycoposerramine T, and (+/-)-lycopoclavamine B have been accomplished. The functionalized octahydroindane skeleton of these natural products was constructed by an efficient Diels-Alder reaction of an alpha-alkynylcyclopentenone and the stereoselective introduction of a tertiary hydroxyl group. Two of these natural products were divergently synthesized from the same synthetic intermediate at a later stage.

  DOI：

  10.1021/ol400628h

文献信息

• Syntheses of (±)-Serratine, (±)-Lycoposerramine T, and (±)-Lycopoclavamine B
  作者：Hisaaki Zaimoku、Hiroshi Nishide、Asami Nishibata、Naoya Goto、Tsuyoshi Taniguchi、Hiroyuki Ishibashi

  DOI：10.1021/ol400628h

  日期：2013.5.3

  The first total syntheses of (+/-)-serratine, (+/-)-lycoposerramine T, and (+/-)-lycopoclavamine B have been accomplished. The functionalized octahydroindane skeleton of these natural products was constructed by an efficient Diels-Alder reaction of an alpha-alkynylcyclopentenone and the stereoselective introduction of a tertiary hydroxyl group. Two of these natural products were divergently synthesized from the same synthetic intermediate at a later stage.