methyl 5-methyl-4,6-heptadienoate | 71483-60-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 5-methyl-4,6-heptadienoate
• 英文别名: Methyl 5-methylhepta-4,6-dienoate；methyl 5-methylhepta-4,6-dienoate
• CAS: 71483-60-8
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: DIDVPYYJWVBSOD-UHFFFAOYSA-N

物化性质

• 沸点：
  56 °C(Press: 2 Torr)
• 密度：
  0.9834 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 5-methyl-4,6-heptadienoate 在 palladium diacetate 、 对苯醌 作用下， 以 乙醚 、 溶剂黄146 、 丙酮 为溶剂， 反应 72.5h， 生成 3-(5',5'-Dimethyltetrahydrofuran-2'-yl)-cis-2-buten-1-ol acetate
  参考文献：
  名称：

  Synthesis of furanoid terpenes via an efficient palladium-catalyzed cyclization of 4,6-dienols

  摘要：

  The total syntheses of marmelo oxides A and B and a terpene alcohol found in peppermint oil are described. The key steps in these syntheses are the regioselective palladium-catalyzed allylic substitution of 4 and 11 to 6a and 12, respectively, and the regioselective palladium-catalyzed cyclization of 8 and 14 to 9a, 9b, and 15, respectively. The relative stereochemistry of marmelo oxides A and B was established by NOE measurements.

  DOI：

  10.1021/jo00018a027
• 作为产物：
  描述：

  3-methyl-1,4-pentadien-3-ol 在 palladium diacetate 4-二甲氨基吡啶 、 三丁基膦 、 氰化钠 、 水 、 sodium hydride 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 63.0h， 生成 methyl 5-methyl-4,6-heptadienoate
  参考文献：
  名称：

  Synthesis of furanoid terpenes via an efficient palladium-catalyzed cyclization of 4,6-dienols

  摘要：

  The total syntheses of marmelo oxides A and B and a terpene alcohol found in peppermint oil are described. The key steps in these syntheses are the regioselective palladium-catalyzed allylic substitution of 4 and 11 to 6a and 12, respectively, and the regioselective palladium-catalyzed cyclization of 8 and 14 to 9a, 9b, and 15, respectively. The relative stereochemistry of marmelo oxides A and B was established by NOE measurements.

  DOI：

  10.1021/jo00018a027

文献信息

• Synthesis of furanoid terpenes via an efficient palladium-catalyzed cyclization of 4,6-dienols
  作者：Pher G. Andersson、Jan E. Baeckvall

  DOI：10.1021/jo00018a027

  日期：1991.8

  The total syntheses of marmelo oxides A and B and a terpene alcohol found in peppermint oil are described. The key steps in these syntheses are the regioselective palladium-catalyzed allylic substitution of 4 and 11 to 6a and 12, respectively, and the regioselective palladium-catalyzed cyclization of 8 and 14 to 9a, 9b, and 15, respectively. The relative stereochemistry of marmelo oxides A and B was established by NOE measurements.