2-(2-Fluoro-biphenyl-4-yl)-propan-2-ol | 55258-79-2

• 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: 2-(2-Fluoro-biphenyl-4-yl)-propan-2-ol
• 英文别名: 2-(3-Fluoro-4-phenylphenyl)propan-2-ol；2-(3-fluoro-4-phenylphenyl)propan-2-ol
• CAS: 55258-79-2
• 化学式: C₁₅H₁₅FO
• 分子量: 230.282
• InChiKey: OAMVZAMWAPSJHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-Fluoro-biphenyl-4-yl)-propan-2-ol 在 AD-mix-α 、 甲基磺酰氯 、 三乙胺 作用下， 生成 (S)-2-(2-Fluoro-biphenyl-4-yl)-propane-1,2-diol
  参考文献：
  名称：

  Asymmetric dihydroxylation in an approach to the enantioselective synthesis of 2-arylpropanoic acid non-steroidal anti-inflammatory drugs

  摘要：

  Naproxen ((S)-2-(6-methoxy-2-naphthyl)propanoic acid) and flurbiprofen ((S)-2-(3-fluoro-4-phenylphenyl)propanoic acid) have been synthesised in high enantiomeric excess. The synthetic strategy employed was to introduce asymmetry into the molecules by Sharpless asymmetric dihydroxylation of the appropriate methyl styrenes. The resultant diols were then converted into optically active epoxides and the required stereogenic centre was assembled by catalytic hydrogenolysis of the introduced benzylic epoxide oxygen bond, followed by oxidation of the derived optically active primary alcohol. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00026-8
• 作为产物：
  描述：

  丙酮 、 2-FLUORO-4-BIPHENYLMAGNESIUM BROMIDE 生成 2-(2-Fluoro-biphenyl-4-yl)-propan-2-ol
  参考文献：
  名称：

  Asymmetric dihydroxylation in an approach to the enantioselective synthesis of 2-arylpropanoic acid non-steroidal anti-inflammatory drugs

  摘要：

  Naproxen ((S)-2-(6-methoxy-2-naphthyl)propanoic acid) and flurbiprofen ((S)-2-(3-fluoro-4-phenylphenyl)propanoic acid) have been synthesised in high enantiomeric excess. The synthetic strategy employed was to introduce asymmetry into the molecules by Sharpless asymmetric dihydroxylation of the appropriate methyl styrenes. The resultant diols were then converted into optically active epoxides and the required stereogenic centre was assembled by catalytic hydrogenolysis of the introduced benzylic epoxide oxygen bond, followed by oxidation of the derived optically active primary alcohol. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00026-8

文献信息

• FR2231393
  申请人：——

  公开号：——

  公开（公告）日：——
• Asymmetric dihydroxylation in an approach to the enantioselective synthesis of 2-arylpropanoic acid non-steroidal anti-inflammatory drugs
  作者：Robert C. Griesbach、David P.G. Hamon、Rebecca J. Kennedy

  DOI：10.1016/s0957-4166(97)00026-8

  日期：1997.2

  Naproxen ((S)-2-(6-methoxy-2-naphthyl)propanoic acid) and flurbiprofen ((S)-2-(3-fluoro-4-phenylphenyl)propanoic acid) have been synthesised in high enantiomeric excess. The synthetic strategy employed was to introduce asymmetry into the molecules by Sharpless asymmetric dihydroxylation of the appropriate methyl styrenes. The resultant diols were then converted into optically active epoxides and the required stereogenic centre was assembled by catalytic hydrogenolysis of the introduced benzylic epoxide oxygen bond, followed by oxidation of the derived optically active primary alcohol. (C) 1997 Elsevier Science Ltd.