Ethyl 6-(2-cyanoethyl)-1,4-dioxaspiro[4.5]dec-6-ene-9-carboxylate | 195964-71-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 6-(2-cyanoethyl)-1,4-dioxaspiro[4.5]dec-6-ene-9-carboxylate
• CAS: 195964-71-7
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: NWEJTVFCZVQKCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 6-(2-cyanoethyl)-1,4-dioxaspiro[4.5]dec-6-ene-9-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以64%的产率得到[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
• 作为产物：
  描述：

  Ethyl 4-(2-cyanoethyl)-3,5-dioxocyclohexane-1-carboxylate 在 重氮甲烷 、 sodium tetrahydroborate 、 cerium(III) chloride 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 11.0h， 生成 Ethyl 6-(2-cyanoethyl)-1,4-dioxaspiro[4.5]dec-6-ene-9-carboxylate
  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.