Ethyl 4-(2-cyanoethyl)-5-oxocyclohex-3-ene-1-carboxylate | 195964-70-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 4-(2-cyanoethyl)-5-oxocyclohex-3-ene-1-carboxylate
• CAS: 195964-70-6
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: BGZSUFMANKRTGN-UHFFFAOYSA-N

物化性质

• 沸点：
  381.1±42.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 4-(2-cyanoethyl)-5-oxocyclohex-3-ene-1-carboxylate 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 磺酰氯 、 高氯酸 、 2-硝基苯基丝氰酸酯 、 双氧水 、 sodium carbonate 、 对甲苯磺酸 、 三乙胺 、 silver carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 氯仿 、 乙酸乙酯 、 苯 为溶剂， 反应 131.0h， 生成 1-methoxy-N-(benzyloxycarbonyl)-15,16-didehydrolycodine
  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 作用下， 生成 Ethyl 4-(2-cyanoethyl)-5-oxocyclohex-3-ene-1-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.