5-fluoro-2-[(1S)-1-hydroxyethyl]benzonitrile | 1363508-22-8

• 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: 5-fluoro-2-[(1S)-1-hydroxyethyl]benzonitrile
• CAS: 1363508-22-8
• 化学式: C₉H₈FNO
• 分子量: 165.167
• InChiKey: KBOQWSFIDAJHAV-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基-5-氟苯甲酸 在 盐酸 、 葡萄糖 、 水 、 溶剂黄146 作用下， 以 乙二醇二甲醚 、 乙二醇二乙醚 、 水 为溶剂， 反应 52.08h， 生成 (S)-6-fluoro-3-methyl-2-benzofuran-1(3H)-one 、 5-fluoro-2-[(1S)-1-hydroxyethyl]benzonitrile
  参考文献：
  名称：

  Highly Stereoselective Chemoenzymatic Synthesis of the 3H-Isobenzofuran Skeleton. Access to Enantiopure 3-Methylphthalides

  摘要：

  A straightforward synthesis of (S)-3-methylphthalides has been developed, with the key asymmetric step being the bioreduction of 2-acetylbenzonitriles. Enzymatic processes have been found to be highly dependent on the pH value, with acidic conditions being required to avoid undesired side reactions. Baker's yeast was found lobe the best biocatalyst acting in a highly stereoselective fashion. The simple treatment of the reaction crudes with aqueous HCl has provided access to enantiopure (S)-3-methylphthalides in moderate to excellent yields.

  DOI：

  10.1021/ol300191s

文献信息

• Highly Stereoselective Chemoenzymatic Synthesis of the 3<i>H</i>-Isobenzofuran Skeleton. Access to Enantiopure 3-Methylphthalides
  作者：Juan Mangas-Sánchez、Eduardo Busto、Vicente Gotor-Fernández、Vicente Gotor

  DOI：10.1021/ol300191s

  日期：2012.3.16

  A straightforward synthesis of (S)-3-methylphthalides has been developed, with the key asymmetric step being the bioreduction of 2-acetylbenzonitriles. Enzymatic processes have been found to be highly dependent on the pH value, with acidic conditions being required to avoid undesired side reactions. Baker's yeast was found lobe the best biocatalyst acting in a highly stereoselective fashion. The simple treatment of the reaction crudes with aqueous HCl has provided access to enantiopure (S)-3-methylphthalides in moderate to excellent yields.