1-(N,N-dibenzylamino)-3-fluoro-3-methylbutan-2-ol | 1306772-47-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(N,N-dibenzylamino)-3-fluoro-3-methylbutan-2-ol
• 英文别名: 1-(Dibenzylamino)-3-fluoro-3-methylbutan-2-ol
• CAS: 1306772-47-3
• 化学式: C₁₉H₂₄FNO
• 分子量: 301.404
• InChiKey: YCEDTGCUACLGST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,3-dimethyl-oxirane-2-carbaldehyde 在 四氟硼酸-二乙醚络合物 、 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 16.08h， 生成 1-(N,N-dibenzylamino)-3-fluoro-3-methylbutan-2-ol
  参考文献：
  名称：

  Ring-Opening Hydrofluorination of 2,3- and 3,4-Epoxy Amines by HBF₄·OEt₂: Application to the Asymmetric Synthesis of (S,S)-3-Deoxy-3-fluorosafingol

  摘要：

  Treatment of a range of 2,3- and 3,4-epoxy amines with HBF4 center dot OEt2 at room temperature results in fast and efficient S(N)2-type ring-opening hydrofluorination to give stereodefined amino fluorohydrins. Operational simplicity, scalability, and short reaction time at ambient temperature are notable features of this method, The utility of this methodology is exemplified in a concise asymmetric synthesis of (S,S)-3-deoxy-3-fluorosafingol.

  DOI：

  10.1021/jo200517w

文献信息

• Ring-Opening Hydrofluorination of 2,3- and 3,4-Epoxy Amines by HBF₄·OEt₂: Application to the Asymmetric Synthesis of (<i>S</i>,<i>S</i>)-3-Deoxy-3-fluorosafingol
  作者：Alexander J. Cresswell、Stephen G. Davies、James A. Lee、Melloney J. Morris、Paul M. Roberts、James E. Thomson

  DOI：10.1021/jo200517w

  日期：2011.6.3

  Treatment of a range of 2,3- and 3,4-epoxy amines with HBF4 center dot OEt2 at room temperature results in fast and efficient S(N)2-type ring-opening hydrofluorination to give stereodefined amino fluorohydrins. Operational simplicity, scalability, and short reaction time at ambient temperature are notable features of this method, The utility of this methodology is exemplified in a concise asymmetric synthesis of (S,S)-3-deoxy-3-fluorosafingol.