(S)-1-(5-nitrobenzofuran-2-yl)ethanol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (S)-1-(5-nitrobenzofuran-2-yl)ethanol
• 英文别名: (1S)-1-(5-nitro-1-benzofuran-2-yl)ethanol
• 化学式: C₁₀H₉NO₄
• 分子量: 207.186
• InChiKey: ROFXAZOEFKABSF-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-乙酰基-5-硝基苯并[b]呋喃 在 baker's yeast 、 novozyme 435 、 18-冠醚-6 、 溴 作用下， 以 乙醇 、 水 为溶剂， 反应 27.0h， 生成 (S)-1-(5-nitrobenzofuran-2-yl)ethanol
  参考文献：
  名称：

  Optically active 1-(benzofuran-2-yl)ethanols and ethane-1,2-diols by enantiotopic selective bioreductions

  摘要：

  Enantiotopic selective reduction of 1-(benzofuran-2-yl)ethanones 1a-d, 1-(benzofuran-2-yl)-2-hydroxyethanones 4a-c and 2-acetoxy-1-(benzofuran-2-yl)ethanones 3a-c was performed by baker's yeast for preparation of optically active (benzofuran-2-yl)carbinols [(S)-5a-d, (S)-6a-c and (R)-6a-c, enantiomeric excess from 55 to 93% ee]. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00222-2

文献信息

• Kinetic resolution of 1-(benzofuran-2-yl)ethanols by lipase-catalyzed enantiomer selective reactions
  作者：Csaba Paizs、Monica Toşa、Viktória Bódai、György Szakács、Ildikó Kmecz、Béla Simándi、Cornelia Majdik、Lajos Novák、Florin-Dan Irimie、László Poppe

  DOI：10.1016/s0957-4166(03)00358-6

  日期：2003.7

  Kinetic resolution of racemic 1-(benzofuran-2-yl)ethanols rac-1a-d was performed by lipase-catalyzed enantiomer selective acylation (Emuch greater than100) yielding (1R)-1-acetoxy-1-(benzofuran-2-yl)ethanes (R)-2a-d and (1S)-1-(benzofuran-2-yl)ethanois (S)-1a-d in highly enantiopure form. The degree of enantiomer selectivity for enzymatic alcoholysis/hydrolysis processes starting from racemic 1-acetoxy-1-(benzofuran-2-yl)ethane rac-2 was also tested under various conditions including supercritical CO2 medium. Racemization-free lipase-catalyzed ethanolysis of the (1R)-1-acetoxy-1-(benzofuran-2-yl)ethanes (R)-2a-d yielded almost quantitatively the enantiopure (1R)-1-(benzofuran-2-yl)ethanols (R)-1a-d. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Optically active 1-(benzofuran-2-yl)ethanols and ethane-1,2-diols by enantiotopic selective bioreductions
  作者：Csaba Paizs、Monica Toşa、Cornelia Majdik、Paula Moldovan、Lajos Novák、Pál Kolonits、Adriana Marcovici、Florin-Dan Irimie、László Poppe

  DOI：10.1016/s0957-4166(03)00222-2

  日期：2003.6

  Enantiotopic selective reduction of 1-(benzofuran-2-yl)ethanones 1a-d, 1-(benzofuran-2-yl)-2-hydroxyethanones 4a-c and 2-acetoxy-1-(benzofuran-2-yl)ethanones 3a-c was performed by baker's yeast for preparation of optically active (benzofuran-2-yl)carbinols [(S)-5a-d, (S)-6a-c and (R)-6a-c, enantiomeric excess from 55 to 93% ee]. (C) 2003 Elsevier Science Ltd. All rights reserved.