[6-(3-Aminopropyl)-1,4-dioxaspiro[4.5]dec-6-en-9-yl]methanol | 195964-72-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [6-(3-Aminopropyl)-1,4-dioxaspiro[4.5]dec-6-en-9-yl]methanol
• CAS: 195964-72-8
• 化学式: C₁₂H₂₁NO₃
• 分子量: 227.304
• InChiKey: HMJJJGMRLGIERJ-UHFFFAOYSA-N

物化性质

• 沸点：
  364.3±42.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  64.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [6-(3-Aminopropyl)-1,4-dioxaspiro[4.5]dec-6-en-9-yl]methanol 在 高氯酸 、 sodium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 24.33h， 生成 16-(mesyloxy)-N-(benzyloxycarbonyl)-2,3-dihydrolycodin-1-one
  参考文献：
  名称：

  The First Total Synthesis of (±)-Huperzine B

  摘要：

  Huperzine B, a new Lycopodium alkaloid, exhibits a memory facilitating effect in mice and may be useful as an acetylcholinesterase inhibitor for the treatment of Alzheimer's disease. An efficient synthetic approach to huperzine B has been established successfully. The tetracyclic intermediate 10 is constructed by means of a tandem Michael addition and intramolecular Mannich cyclization using 8 and 9 as two components. Racemic huperzine B is obtained via a reaction sequence of 12 steps in 6.6% overall yield.

  DOI：

  10.1021/jo970248f
• 作为产物：
  描述：

  Ethyl 4-(2-cyanoethyl)-3,5-dioxocyclohexane-1-carboxylate 在 重氮甲烷 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 cerium(III) chloride 、 对甲苯磺酸 作用下， 以 乙醚 、 苯 为溶剂， 反应 13.0h， 生成 [6-(3-Aminopropyl)-1,4-dioxaspiro[4.5]dec-6-en-9-yl]methanol
  参考文献：
  名称：

  The First Total Synthesis of (±)-Huperzine B

  摘要：

  Huperzine B, a new Lycopodium alkaloid, exhibits a memory facilitating effect in mice and may be useful as an acetylcholinesterase inhibitor for the treatment of Alzheimer's disease. An efficient synthetic approach to huperzine B has been established successfully. The tetracyclic intermediate 10 is constructed by means of a tandem Michael addition and intramolecular Mannich cyclization using 8 and 9 as two components. Racemic huperzine B is obtained via a reaction sequence of 12 steps in 6.6% overall yield.

  DOI：

  10.1021/jo970248f

文献信息

• The First Total Synthesis of (±)-Huperzine B
  作者：Baogen Wu、Donglu Bai

  DOI：10.1021/jo970248f

  日期：1997.8.1

  Huperzine B, a new Lycopodium alkaloid, exhibits a memory facilitating effect in mice and may be useful as an acetylcholinesterase inhibitor for the treatment of Alzheimer's disease. An efficient synthetic approach to huperzine B has been established successfully. The tetracyclic intermediate 10 is constructed by means of a tandem Michael addition and intramolecular Mannich cyclization using 8 and 9 as two components. Racemic huperzine B is obtained via a reaction sequence of 12 steps in 6.6% overall yield.