methyl 3,3,5,5-tetramethyl-1-cyclopentene-1-carboxylate

• 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: methyl 3,3,5,5-tetramethyl-1-cyclopentene-1-carboxylate
• 英文别名: 3,3,5,5-tetramethyl-cyclopent-1-enecarboxylic acid methyl ester；3,3,5,5-Tetramethyl-cyclopent-1-encarbonsaeure-methylester；Methyl 3,3,5,5-tetramethylcyclopentene-1-carboxylate；methyl 3,3,5,5-tetramethylcyclopentene-1-carboxylate
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: QZGWISBCOWJUCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,3,5,5-四甲基环己酮 、 sodium methylate 在 sodium iodide 作用下， 以 甲醇 为溶剂， 以31%的产率得到methyl 3,3,5,5-tetramethyl-1-cyclopentene-1-carboxylate
  参考文献：
  名称：

  Indirect electrochemical oxidation of piperidin-4-ones mediated by sodium halide-base system

  摘要：

  Indirect electrochemical oxidation of 1-N-subsituted piperidin-4-ones in methanol in an undivided cell in the presence of sodium iodide/sodium methoxide system leads to the corresponding alpha-hydroxyketals in 50-80% substance yield (50-65% current yield). 2,2,6,6Tetramethylpiperidin-4-one under the same conditions forms a mixture of methyl 2,2,5,5-tetramethyl-3-pyrrolidinecarboxylate and methyl 2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrole-3-carboxylate in 70% substance yield (60-70% current yield) via electrochemically induced Favorskii rearrangement. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.031

文献信息

• Indirect electrochemical oxidation of piperidin-4-ones mediated by sodium halide-base system
  作者：Michail N. Elinson、Alexander S. Dorofeev、Sergey K. Feducovich、Ruslan F. Nasybullin、Evgeny F. Litvin、Mikhail V. Kopyshev、Gennady I. Nikishin

  DOI：10.1016/j.tet.2006.06.031

  日期：2006.8

  Indirect electrochemical oxidation of 1-N-subsituted piperidin-4-ones in methanol in an undivided cell in the presence of sodium iodide/sodium methoxide system leads to the corresponding alpha-hydroxyketals in 50-80% substance yield (50-65% current yield). 2,2,6,6Tetramethylpiperidin-4-one under the same conditions forms a mixture of methyl 2,2,5,5-tetramethyl-3-pyrrolidinecarboxylate and methyl 2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrole-3-carboxylate in 70% substance yield (60-70% current yield) via electrochemically induced Favorskii rearrangement. (c) 2006 Elsevier Ltd. All rights reserved.