(S)-(+)-2-(2-iso-indolinyl)butan-1-ol | 143880-78-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (S)-(+)-2-(2-iso-indolinyl)butan-1-ol
• 英文别名: (2S)-2-(1,3-dihydroisoindol-2-yl)butan-1-ol
• CAS: 143880-78-8
• 化学式: C₁₂H₁₇NO
• 分子量: 191.273
• InChiKey: OGAAQVONYOTBGB-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-(+)-2-氨基-1-丁醇 、 邻二氯苄 在 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 生成 (S)-(+)-2-(2-iso-indolinyl)butan-1-ol
  参考文献：
  名称：

  Synthesis of chiral alcohols by asymmetric reductions of various ketones including α-aminophenones

  摘要：

  LiAlH4 previously treated with 2.5 equiv. of (S)-(+) or (R)-(-)-2-(2-isoindolinyl)butan-1-ol 1 reduced the six alpha-aminophenones 4-9 into the corresponding optically active beta-aminoalcohols 10-15 whose ee's were in the range 40-97% after chromatography and recrystallization. The asymmetric reduction of the ortho-dimethylaminobenzophenone 18, using the same reducing agents afforded the enantiomerically pure benzhydrols (R)-(-)-19 and (S)-(+)-19, respectively, and in 86-100% yields. The ortho-aminobenzhydrol (S)-(+)-20 and a-fluorenyl ethanol (R)-(+)-23 and (S)-(-)-23 were similarly obtained from the corresponding ketones 17 and 25, respectively. The latter carbinols were obtained in an enantiomerically pure state after recrystallization. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00245-5
• 作为试剂：
  描述：

  9-acetylfluorene 在 lithium aluminium tetrahydride 、 (S)-(+)-2-(2-iso-indolinyl)butan-1-ol 作用下， 以 乙醚 为溶剂， 反应 19.0h， 以36%的产率得到(S)-(-)-1-(9-芴)乙醇
  参考文献：
  名称：

  Synthesis of chiral alcohols by asymmetric reductions of various ketones including α-aminophenones

  摘要：

  LiAlH4 previously treated with 2.5 equiv. of (S)-(+) or (R)-(-)-2-(2-isoindolinyl)butan-1-ol 1 reduced the six alpha-aminophenones 4-9 into the corresponding optically active beta-aminoalcohols 10-15 whose ee's were in the range 40-97% after chromatography and recrystallization. The asymmetric reduction of the ortho-dimethylaminobenzophenone 18, using the same reducing agents afforded the enantiomerically pure benzhydrols (R)-(-)-19 and (S)-(+)-19, respectively, and in 86-100% yields. The ortho-aminobenzhydrol (S)-(+)-20 and a-fluorenyl ethanol (R)-(+)-23 and (S)-(-)-23 were similarly obtained from the corresponding ketones 17 and 25, respectively. The latter carbinols were obtained in an enantiomerically pure state after recrystallization. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00245-5

文献信息

• Preparative synthesis of optically pure ortho-substituted benzhydrols by asymmetric reductions of the corresponding benzophenones
  作者：Eric Brown、Antoine Lézé、Joël Touet

  DOI：10.1016/s0957-4166(00)82179-5

  日期：1992.7

  Lithium aluminium hydride previously treated with 2.5 equivalents of (S)-(+) or (R)-(-)-2 -(2-iso-indolinyl)butan-1-ol 3 (readily available reagents) reduced the five ortho-substituted benzophenones 4-6, 8 and 10 into the corresponding optically active benzhydrols with nearly 100% enantiomeric excesses. Other examples of asymmetric reductions of prochiral benzophenones are given.