(2R)-4-(2-fluorophenyl)-1-phenylmethoxybut-3-yn-2-ol | 141939-68-6

• 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: (2R)-4-(2-fluorophenyl)-1-phenylmethoxybut-3-yn-2-ol
• CAS: 141939-68-6
• 化学式: C₁₇H₁₅FO₂
• 分子量: 270.303
• InChiKey: SGUNNVRLUBRQBN-MRXNPFEDSA-N

物化性质

• 沸点：
  415.5±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2R)-4-(2-fluorophenyl)-1-phenylmethoxybut-3-yn-2-ol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以80.2%的产率得到(E,2R)-4-(2-fluorophenyl)-1-phenylmethoxybut-3-en-2-ol
  参考文献：
  名称：

  An Efficient Synthesis of Optically Active 4-Benzyloxy-3-hydoroxy-1-butyne and Its Cross-Coupling Reaction

  摘要：

  An efficient procedure for the synthesis of optically active 4-benzyloxy-3-hydroxy-1-butyne (12: R = H) has been established starting with optically active tartrate ester. Cross-coupling reaction of the resulted acetylene (12: R = H) with some aromatic halides (13a approximately h) and transformation of the arylacetylenes (14a approximate h), thus obtained, into the allylic amine derivatives (17a approximate h) have also been examined via the allylic alcohol intermediates (15 a approximately h) by sequential stereoselective reduction and [3,3] sigmatropic rearrangement.

  DOI：

  10.3987/com-91-s89
• 作为产物：
  描述：

  2-氟碘苯 、 (R)-4-benzyloxy-3-hydroxy-1-butyne 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 反应 2.0h， 以76.2%的产率得到(2R)-4-(2-fluorophenyl)-1-phenylmethoxybut-3-yn-2-ol
  参考文献：
  名称：

  An Efficient Synthesis of Optically Active 4-Benzyloxy-3-hydoroxy-1-butyne and Its Cross-Coupling Reaction

  摘要：

  An efficient procedure for the synthesis of optically active 4-benzyloxy-3-hydroxy-1-butyne (12: R = H) has been established starting with optically active tartrate ester. Cross-coupling reaction of the resulted acetylene (12: R = H) with some aromatic halides (13a approximately h) and transformation of the arylacetylenes (14a approximate h), thus obtained, into the allylic amine derivatives (17a approximate h) have also been examined via the allylic alcohol intermediates (15 a approximately h) by sequential stereoselective reduction and [3,3] sigmatropic rearrangement.

  DOI：

  10.3987/com-91-s89