ethyl 4,4-difluoro-3-hydroxy-2-nitro-2-butanoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 4,4-difluoro-3-hydroxy-2-nitro-2-butanoate
• 英文别名: ethyl 4,4-difluoro-3-hydroxy-2-nitrobutanoate
• 化学式: C₆H₉F₂NO₅
• 分子量: 213.138
• InChiKey: SBDWJOZAKMTQTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 4,4-difluoro-3-hydroxy-2-nitro-2-butanoate 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 反应 24.0h， 以73.7%的产率得到(2S,3R)-2-Amino-4,4-difluoro-3-hydroxy-butyric acid ethyl ester
  参考文献：
  名称：

  A remarkably simple route to versatile difluoromethylated molecules

  摘要：

  Difluoroacetaldehyde ethyl hemiacetal (1), prepared from ethyl difluoroacetate and lithium aluminum hydride in diethyl ether, was found to be a potential difluoroethylating reagent for the preparation of a wide variety of difluoromethylated compounds. Compound 1 shows promise for use in the synthesis of carbinols prepared by the reaction of 1 with metal reagents or enol silyl ethers, the synthesis of amino acid ketones and beta-lactams via the nucleophilic reaction of imines, and the synthesis of sugar analogues.

  DOI：

  10.1021/jo00060a055
• 作为产物：
  描述：

  硝基乙酸乙酯 、 二氟乙醛缩半乙醇 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到ethyl 4,4-difluoro-3-hydroxy-2-nitro-2-butanoate
  参考文献：
  名称：

  A remarkably simple route to versatile difluoromethylated molecules

  摘要：

  Difluoroacetaldehyde ethyl hemiacetal (1), prepared from ethyl difluoroacetate and lithium aluminum hydride in diethyl ether, was found to be a potential difluoroethylating reagent for the preparation of a wide variety of difluoromethylated compounds. Compound 1 shows promise for use in the synthesis of carbinols prepared by the reaction of 1 with metal reagents or enol silyl ethers, the synthesis of amino acid ketones and beta-lactams via the nucleophilic reaction of imines, and the synthesis of sugar analogues.

  DOI：

  10.1021/jo00060a055

文献信息

• [EN] DERIVATIVES OF GLYCO-CF2-SERINE AND GLYCO-CF2-THREONINE<br/>[FR] DÉRIVÉS DE GLYCO-CF2-SÉRINE ET DE GLYCO-CF2-THRÉONINE
  申请人：TFCHEM

  公开号：WO2012085221A1

  公开（公告）日：2012-06-28

  The present invention relates to compounds of formula (I): or a pharmaceutically acceptable salt thereof, a tautomer, a stereoisomer or a mixture of stereoisomers in any proportion, in particular a mixture of enantiomers, and particularly a racemate mixture, as well as to their process of preparation, their use in the peptide synthesis, said peptide and the use of said peptide.

  本发明涉及式(I)的化合物：或其药学上可接受的盐，互变异构体，立体异构体或任意比例的立体异构体混合物，特别是对映体混合物的混合物，尤其是外消旋混合物，以及它们的制备方法，它们在肽合成中的应用，所述肽及所述肽的应用。
• The synthesis of fluorinated materials in microreactors
  作者：Kouichi Kawai、Takuma Ebata、Tomoya Kitazume

  DOI：10.1016/j.jfluchem.2005.04.010

  日期：2005.6

  Synthetic utilities of microreactor for the synthesis of fluorinated materials are described. In particular, synthesis of silylenol ether of 4,4,4-trifluorobutan-2-one and its synthetic application at room temperature. Further, nitroaldol reactions and Michael addition reaction in microreactor are convenient ways for the syntheses of difluoromethylated materials. (C) 2005 Elsevier B.V. All rights reserved.