(E,E)-diethyl 2-[but-2-enyl]-2-[3,7-dimethylocta-2,6-dienyl]malonate | 1310543-95-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (E,E)-diethyl 2-[but-2-enyl]-2-[3,7-dimethylocta-2,6-dienyl]malonate
• 英文别名: diethyl 2-[(E)-but-2-enyl]-2-[(2E)-3,7-dimethylocta-2,6-dienyl]propanedioate
• CAS: 1310543-95-3
• 化学式: C₂₁H₃₄O₄
• 分子量: 350.499
• InChiKey: LQKLSIFHBQVDIF-BXDKFJHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E,E)-diethyl 2-[but-2-enyl]-2-[3,7-dimethylocta-2,6-dienyl]malonate 在 bismuth(lll) trifluoromethanesulfonate 作用下， 以 硝基甲烷 为溶剂， 反应 0.08h， 以81%的产率得到diethyl 4-ethyl-4,8,8-trimethyl-1,2,3,4,5,6,7,8-octahydronaphthalene-2,2-dicarboxylate
  参考文献：
  名称：

  Biomimetic Cationic Polyannulation Reaction Catalyzed by Bi(OTf)₃: Cyclization of 1,6-Dienes, 1,6,10-Trienes, and Aryl Polyenes

  摘要：

  Nonactivated trienes and aryltrienes were cyclized into polycyclic compounds in good to excellent yields under bismuth triflate catalysis in a biomimetic fashion. The reaction showed broad applicability and allowed for the formation of functionalized bicyclic to tetracyclic structures from simple precursors in one pot. For some specific substrates, the cyclization was followed by a methyl shift as encountered in terpenoid biosynthesis.

  DOI：

  10.1021/ol201028f
• 作为产物：
  描述：

  香叶基溴 在 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 (E,E)-diethyl 2-[but-2-enyl]-2-[3,7-dimethylocta-2,6-dienyl]malonate
  参考文献：
  名称：

  Biomimetic Cationic Polyannulation Reaction Catalyzed by Bi(OTf)₃: Cyclization of 1,6-Dienes, 1,6,10-Trienes, and Aryl Polyenes

  摘要：

  Nonactivated trienes and aryltrienes were cyclized into polycyclic compounds in good to excellent yields under bismuth triflate catalysis in a biomimetic fashion. The reaction showed broad applicability and allowed for the formation of functionalized bicyclic to tetracyclic structures from simple precursors in one pot. For some specific substrates, the cyclization was followed by a methyl shift as encountered in terpenoid biosynthesis.

  DOI：

  10.1021/ol201028f

文献信息

• Biomimetic Cationic Polyannulation Reaction Catalyzed by Bi(OTf)₃: Cyclization of 1,6-Dienes, 1,6,10-Trienes, and Aryl Polyenes
  作者：Julien Godeau、Sandra Olivero、Sylvain Antoniotti、Elisabet Duñach

  DOI：10.1021/ol201028f

  日期：2011.7.1

  Nonactivated trienes and aryltrienes were cyclized into polycyclic compounds in good to excellent yields under bismuth triflate catalysis in a biomimetic fashion. The reaction showed broad applicability and allowed for the formation of functionalized bicyclic to tetracyclic structures from simple precursors in one pot. For some specific substrates, the cyclization was followed by a methyl shift as encountered in terpenoid biosynthesis.