trans-5,6-dihydro-6-isopropoxy-1,10-phenanthrolin-5-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: trans-5,6-dihydro-6-isopropoxy-1,10-phenanthrolin-5-ol
• 英文别名: trans-5,6-dihydro-5-hydroxy-6-isopropoxy-1,10-phenanthroline；(5S,6S)-6-propan-2-yloxy-5,6-dihydro-1,10-phenanthrolin-5-ol
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: MSPZVAGLMORVHS-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  异丙醇 、 5,6-epoxy-5,6-dihydro-[1,10]phenanthroline 在 ytterbium(III) triflate 作用下， 以99%的产率得到trans-5,6-dihydro-6-isopropoxy-1,10-phenanthrolin-5-ol
  参考文献：
  名称：

  Efficient alcoholysis of 5,6-dihydro-1,10-phenanthroline-5,6-epoxide with ytterbium(III) triflate and subsequent enantioselective transesterification with lipases

  摘要：

  New 5,6-dihydro-1,10-phenanthroline derivatives were prepared in high yield via ytterbium(III) triflate-catalyzed alcoholysis of the corresponding epoxide. Enzymatic transesterifications of racemic alkoxy alcohols afforded enantioselective separations with up to 99% ee. The lipase derived from Burkholderia cepacia (PSCI) was the most efficient, with E-values of up to 200. The steric effect of substituents in the 6-position on reaction time and enantioselectivities was assessed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.021

文献信息

• Efficient alcoholysis of 5,6-dihydro-1,10-phenanthroline-5,6-epoxide with ytterbium(III) triflate and subsequent enantioselective transesterification with lipases
  作者：Elke Schoffers、Lars Kohler

  DOI：10.1016/j.tetasy.2009.07.021

  日期：2009.8

  New 5,6-dihydro-1,10-phenanthroline derivatives were prepared in high yield via ytterbium(III) triflate-catalyzed alcoholysis of the corresponding epoxide. Enzymatic transesterifications of racemic alkoxy alcohols afforded enantioselective separations with up to 99% ee. The lipase derived from Burkholderia cepacia (PSCI) was the most efficient, with E-values of up to 200. The steric effect of substituents in the 6-position on reaction time and enantioselectivities was assessed. (C) 2009 Elsevier Ltd. All rights reserved.