methyl 4-amino-6,6-difluoro-2,3,4,6-tetradeoxyhexapyranoside | 148628-61-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-amino-6,6-difluoro-2,3,4,6-tetradeoxyhexapyranoside
• 英文别名: 2-(Difluoromethyl)-6-methoxyoxan-3-amine
• CAS: 148628-61-9
• 化学式: C₇H₁₃F₂NO₂
• 分子量: 181.183
• InChiKey: NZVBQDQFZZSVRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl 4-amino-6,6-difluoro-2,3,4,6-tetradeoxyhexapyranoside 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以80.6%的产率得到methyl 4-acetamido-6,6-difluoro-2,3,4,6-tetradeoxyhexapyranoside
  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：

  methyl 6,6-difluoro-4-nitro-2,3,4,6-tetradeoxyhexapyranoside 在 palladium on activated charcoal 氢气 作用下， 以 乙醚 为溶剂， 以49%的产率得到methyl 4-amino-6,6-difluoro-2,3,4,6-tetradeoxyhexapyranoside
  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.