(1R)-1-acetoxy-1-(7-methoxybenzofuran-2-yl)ethane | 600727-11-5

• 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: (1R)-1-acetoxy-1-(7-methoxybenzofuran-2-yl)ethane
• CAS: 600727-11-5
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: HKUNKLNKEYBKSW-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  48.67
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R)-1-acetoxy-1-(7-methoxybenzofuran-2-yl)ethane 在 Lipozyme TL IM 作用下， 以 乙醇 为溶剂， 以96%的产率得到(R)-1-(7-methoxybenzofuran-2-yl)ethanol
  参考文献：
  名称：

  Kinetic resolution of 1-(benzofuran-2-yl)ethanols by lipase-catalyzed enantiomer selective reactions

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(03)00358-6
• 作为产物：
  描述：

  乙酸乙烯酯 、 1-(7-methoxybenzofuran-2-yl)ethanol 在 lipase TUB 3b 作用下， 反应 168.0h， 生成 (S)-1-(7-methoxybenzofuran-2-yl)ethanol 、 (1R)-1-acetoxy-1-(7-methoxybenzofuran-2-yl)ethane
  参考文献：
  名称：

  Kinetic resolution of 1-(benzofuran-2-yl)ethanols by lipase-catalyzed enantiomer selective reactions

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(03)00358-6