2,2,5,5-tetramethyl-2,5-dihydropyrrole-3-carboxylic acid ethyl ester | 308106-20-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 2,2,5,5-tetramethyl-2,5-dihydropyrrole-3-carboxylic acid ethyl ester
• 英文别名: ethyl 2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrole-3-carboxylate；2,2,5,5-tetramethyl-2,5-dihydro-pyrrole-3-carboxylic acid ethyl ester；2,2,5,5-Tetramethyl-2,5-dihydro-pyrrol-3-carbonsaeure-aethylester；ethyl 2,2,5,5-tetramethyl-1H-pyrrole-3-carboxylate
• CAS: 308106-20-9
• 化学式: C₁₁H₁₉NO₂
• 分子量: 197.277
• InChiKey: TXQWQANPWYFKSH-UHFFFAOYSA-N

物化性质

• 沸点：
  120-122 °C(Press: 12 Torr)
• 密度：
  0.953±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2,5,5-tetramethyl-2,5-dihydropyrrole-3-carboxylic acid ethyl ester 在 甲醇 、 氨 作用下， 生成 2,2,5,5-四甲基-3-吡咯啉-3-甲酰胺
  参考文献：
  名称：

  Pauly; Rossbach, Chemische Berichte, 1899, vol. 32, p. 2005

  摘要：

  DOI：
• 作为产物：
  描述：

  乙醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 生成 2,2,5,5-tetramethyl-2,5-dihydropyrrole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Pauly; Rossbach, Chemische Berichte, 1899, vol. 32, p. 2005

  摘要：

  DOI：

文献信息

• Facile Synthesis of 3-Methoxycarbonyl-2,2,5,5-tetra-methylpyrrolidine-1-oxyl and Derivatives
  作者：Bunpei Hatano、Hiroki Araya、Yutaka Yoshimura、Haruna Sato、Tomohiro Ito、Tateaki Ogata、Tatsuro Kijima

  DOI：10.3987/com-09-11861

  日期：——

  We have achieved an efficient alternative synthesis of blood-brain-barrier permeable nitroxyl radicals 3-methoxycarbonyl-2,2,5,5-tetramethylpyrrolidine-1-oxyl (1a) and 3-ethoxycarbonyl-2,2,5,5-tetramethylpyrrolidine-1-oxyl (1b), which affords la and 1b in 65% isolated yields by four steps from 2,2,6.6-tetramethyl-4-piperidone (2), respectively. This protocol is applicable to the synthesis of 3-isopropoxy-2,2,5,5-tetramethylpyrrolidine-1-oxyl (1c) and 3-carbonyl-2,2,5,5-tetramethylpyrro-lidine-1-oxyl (6).
• 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.
• Pauly; Rossbach, Chemische Berichte, 1899, vol. 32, p. 2005
  作者：Pauly、Rossbach

  DOI：——

  日期：——