ethyl 4,4-difluoro-2,2-dimethyl-3-hydroxybutanoate | 148628-47-1

• 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: ethyl 4,4-difluoro-2,2-dimethyl-3-hydroxybutanoate
• 英文别名: Ethyl 4,4-difluoro-3-hydroxy-2,2-dimethylbutanoate
• CAS: 148628-47-1
• 化学式: C₈H₁₄F₂O₃
• 分子量: 196.194
• InChiKey: MZUKWCKEVYAHBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4,4-difluoro-2,2-dimethyl-3-hydroxybutanoate 在 氢氧化钾 作用下， 以 四氢呋喃 为溶剂， 生成 4,4-Difluoro-3-hydroxy-2,2-dimethyl-butyric acid
  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：

  2-溴-2-甲基丙酸乙酯 、 二氟乙醛缩半乙醇 在 锌 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以74%的产率得到ethyl 4,4-difluoro-2,2-dimethyl-3-hydroxybutanoate
  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

• A remarkably simple route to versatile difluoromethylated molecules
  作者：Sadanori Kaneko、Takashi Yamazaki、Tomoya Kitazume

  DOI：10.1021/jo00060a055

  日期：1993.4

  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.