2-allylcyclohexanone dimethyl acetal | 88441-90-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-allylcyclohexanone dimethyl acetal
• 英文别名: 2-(2-propenyl)cyclohexanone dimethyl acetal；Cyclohexane, 1,1-dimethoxy-2-(2-propenyl)-；1,1-dimethoxy-2-prop-2-enylcyclohexane
• CAS: 88441-90-1
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: MUIZJTUGZQEITK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  2-allylcyclohexanone dimethyl acetal 在 咪唑 、 盐酸 、 sodium hydroxide 、 正丁基锂 、 2-甲基-2-丁烯 、 草酰氯 、 dimethyl sulfide borane 、 四丁基氟化铵 、 双氧水 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 61.17h， 生成 1-(methoxy-(E,Z)-methylidene)-2-(4-methyl-5-(trimethylsilyl)-(E,Z)-3-pentenyl)cyclohexane
  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：

  2-烯丙基环己酮 、 原甲酸三甲酯 在 K-10 Montmorillonite clay 作用下， 以91%的产率得到2-allylcyclohexanone dimethyl acetal
  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

• Ring expansion and cleavage of succinoin derivatives. Geminal acylation, reductive succinoylation, and stereoselective spiro annelation methods
  作者：Junichi Shimada、Koichi Hashimoto、Byeang Hyean Kim、Eiichi Nakamura、Isao Kuwajima

  DOI：10.1021/ja00318a035

  日期：1984.3
• SHIMADA, J. -ICHI;HASHIMOTO, KOICHI;KIM, BYEANG, HYEAN;NAKAMURA, EIICHI;K+, J. AMER. CHEM. SOC., 1984, 106, N 6, 1759-1773
  作者：SHIMADA, J. -ICHI、HASHIMOTO, KOICHI、KIM, BYEANG, HYEAN、NAKAMURA, EIICHI、K+

  DOI：——

  日期：——
• 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.