4,4-dimethyl-1-(dimethoxymethyl)-2-(1-methyl-1-ethenyl)-cyclopentane | 184828-18-0

• 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: 4,4-dimethyl-1-(dimethoxymethyl)-2-(1-methyl-1-ethenyl)-cyclopentane
• 英文别名: 3-(Dimethoxymethyl)-1,1-dimethyl-4-prop-1-en-2-ylcyclopentane
• CAS: 184828-18-0
• 化学式: C₁₃H₂₄O₂
• 分子量: 212.332
• InChiKey: SBXTWUBSXXRPLD-UHFFFAOYSA-N

物化性质

• 沸点：
  236.7±13.0 °C(Predicted)
• 密度：
  0.894±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4-dimethyl-1-(dimethoxymethyl)-2-(1-methyl-1-ethenyl)-cyclopentane 在 四丁基氢氧化铵 氢氧化钾 、 amberlyst-15 、 水 、 臭氧 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 乙醚 、 丙酮 为溶剂， 反应 25.17h， 生成 (3aSR,6aSR)-5,5-dimethyl-1,3a,4,5,6,6a-hexahydro-1-pentalenone
  参考文献：
  名称：

  Intramolecular Anodic Olefin Coupling Reactions: A New Approach to the Synthesis of Angularly Fused, Tricyclic Enones

  摘要：

  A number of intramolecular anodic olefin coupling reactions have been examined in order to determine the feasibility of using a sequential electrochemical oxidation-aldol condensation approach for constructing polycyclic enones. Initially, substrates comprised of an aldehyde enol ether tethered to a ketone enol ether were examined. In a model study, it was shown that such a substrate could lead to a successful electrochemical oxidation-aldol condensation sequence. However, the difficulties associated with both the synthesis and the poor stability of the ketone enol ethers greatly reduced the potential utility of this approach. This problem was circumvented by taking advantage of the compatibility of allylsilane groups with the electrolysis reaction. In these examples, ozonolysis of the electrochemical cyclization product afforded the 1,4-dicarbonyl substrate needed for the aldol condensation. The use of the less reactive allylsilane group in the electrochemical reaction still allowed for the construction of quaternary carbons. Finally a pair of angularly fused, tricyclic enones were synthesized. The regiochemistry of the enone in the product could be controlled by the proper choice of the substrate for the electrolysis and manipulation of the resulting cyclized product.

  DOI：

  10.1021/jo00088a019
• 作为产物：
  描述：

  3,3-dimethyl-6-methyl-7-(trimethylsilyl)-5-(E,Z)-hepten-1-ol 在 草酰氯 、 叔丁基锂 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 18.67h， 生成 4,4-dimethyl-1-(dimethoxymethyl)-2-(1-methyl-1-ethenyl)-cyclopentane
  参考文献：
  名称：

  Intramolecular Anodic Olefin Coupling Reactions: A New Approach to the Synthesis of Angularly Fused, Tricyclic Enones

  摘要：

  A number of intramolecular anodic olefin coupling reactions have been examined in order to determine the feasibility of using a sequential electrochemical oxidation-aldol condensation approach for constructing polycyclic enones. Initially, substrates comprised of an aldehyde enol ether tethered to a ketone enol ether were examined. In a model study, it was shown that such a substrate could lead to a successful electrochemical oxidation-aldol condensation sequence. However, the difficulties associated with both the synthesis and the poor stability of the ketone enol ethers greatly reduced the potential utility of this approach. This problem was circumvented by taking advantage of the compatibility of allylsilane groups with the electrolysis reaction. In these examples, ozonolysis of the electrochemical cyclization product afforded the 1,4-dicarbonyl substrate needed for the aldol condensation. The use of the less reactive allylsilane group in the electrochemical reaction still allowed for the construction of quaternary carbons. Finally a pair of angularly fused, tricyclic enones were synthesized. The regiochemistry of the enone in the product could be controlled by the proper choice of the substrate for the electrolysis and manipulation of the resulting cyclized product.

  DOI：

  10.1021/jo00088a019

文献信息

• Anodic electrochemistry and the use of a 6-volt lantern battery: A simple method for attempting electrochemically based synthetic transformations
  作者：Dean A. Frey、Nicholas Wu、Kevin D. Moeller

  DOI：10.1016/0040-4039(96)01946-6

  日期：1996.11

  A series of electrochemical transformations have been accomplished using a 6-volt lantern battery as a power supply. The reactions included both intramolecular anodic olefin coupling reactions and an anodic amide oxidation. In all cases, the reactions afforded preparatively useful amounts of product and demonstrated that electrochemical synthetic methods can be readily attempted without the need for

  使用6伏彩灯电池作为电源，已经完成了一系列的电化学转换。反应包括分子内阳极烯烃偶联反应和阳极酰胺氧化。在所有情况下，反应提供了制备上有用量的产物，并证明了无需专用设备即可容易地尝试电化学合成方法。
• Intramolecular Anodic Olefin Coupling Reactions: A New Approach to the Synthesis of Angularly Fused, Tricyclic Enones
  作者：Luzviminda V. Tinao-Wooldridge、Kevin D. Moeller、Christine M. Hudson

  DOI：10.1021/jo00088a019

  日期：1994.5

  A number of intramolecular anodic olefin coupling reactions have been examined in order to determine the feasibility of using a sequential electrochemical oxidation-aldol condensation approach for constructing polycyclic enones. Initially, substrates comprised of an aldehyde enol ether tethered to a ketone enol ether were examined. In a model study, it was shown that such a substrate could lead to a successful electrochemical oxidation-aldol condensation sequence. However, the difficulties associated with both the synthesis and the poor stability of the ketone enol ethers greatly reduced the potential utility of this approach. This problem was circumvented by taking advantage of the compatibility of allylsilane groups with the electrolysis reaction. In these examples, ozonolysis of the electrochemical cyclization product afforded the 1,4-dicarbonyl substrate needed for the aldol condensation. The use of the less reactive allylsilane group in the electrochemical reaction still allowed for the construction of quaternary carbons. Finally a pair of angularly fused, tricyclic enones were synthesized. The regiochemistry of the enone in the product could be controlled by the proper choice of the substrate for the electrolysis and manipulation of the resulting cyclized product.