diethyl 2-(2,2,2-trifluoro-1-hydroxyethyl)malonate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: diethyl 2-(2,2,2-trifluoro-1-hydroxyethyl)malonate
• 英文别名: diethyl (2,2,2-trifluoro-1-hydroxyethyl)malonate；diethyl 2-(2,2,2-trifluoro-1-hydroxyethyl)propanedioate
• 化学式: C₉H₁₃F₃O₅
• 分子量: 258.194
• InChiKey: MJLGCAZDDADWAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  diethyl 2-(2,2,2-trifluoro-1-hydroxyethyl)malonate 在 水 、 lithium chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 生成 3-羟基-4,4,4-三氟丁酸乙酯
  参考文献：
  名称：

  Utilization of perfluoroalkanoate-derived aluminium acetals as the convenient fluorinated aldehyde precursors

  摘要：

  Aluminium acetals from the DIBAL partial reduction of perfluoroalkanoates 1 were successfully employed as the convenient and useful fluorinated aldehyde precursors, and reactions of such intermediates with sodium salts from some beta-dicarbonyl compounds 2 as well as their possible utility as the Michael acceptors after transformation to the corresponding alkylidene malonates 8 were also demonstrated. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.007
• 作为产物：
  描述：

  丙二酸二乙酯钠盐 、 三氟乙酸乙酯 在 二异丁基氢化铝 、 盐酸 作用下， 以 二氯甲烷 、 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以64%的产率得到diethyl 2-(2,2,2-trifluoro-1-hydroxyethyl)malonate
  参考文献：
  名称：

  Utilization of perfluoroalkanoate-derived aluminium acetals as the convenient fluorinated aldehyde precursors

  摘要：

  Aluminium acetals from the DIBAL partial reduction of perfluoroalkanoates 1 were successfully employed as the convenient and useful fluorinated aldehyde precursors, and reactions of such intermediates with sodium salts from some beta-dicarbonyl compounds 2 as well as their possible utility as the Michael acceptors after transformation to the corresponding alkylidene malonates 8 were also demonstrated. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.007

文献信息

• Unexpected and Expeditious Entry into Trifluoromethyl Aziridines from Substituted β-Dicarbonyl Compounds
  作者：Daniele Colantoni、Stefania Fioravanti、Lucio Pellacani、Paolo A. Tardella

  DOI：10.1021/jo0515327

  日期：2005.11.1

  One-pot aziridinations were obtained starting from substituted 2,2,2-trifluoroethyl β-dicarbonyl compounds with nosyloxycarbamates in the presence of an excess of CaO as base. The unexpected ring closure reaction takes place at room temperature, leading to the N-protected α-trifluoromethyl aziridines with good yields. The reaction pathway seems to be influenced by the choice of the base.

  在存在过量的CaO作为碱的情况下，从用壬基氧基氨基甲酸酯取代的2,2,2-三氟乙基β-二羰基化合物开始，进行一锅叠氮化。意外的闭环反应在室温下发生，从而以良好的收率得到N-保护的α-三氟甲基氮丙啶。反应途径似乎受到碱基选择的影响。