ethyl (2R)-2-(1,3-benzodioxol-5-yl)-2-hydroxyacetate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: ethyl (2R)-2-(1,3-benzodioxol-5-yl)-2-hydroxyacetate
• 化学式: C₁₁H₁₂O₅
• 分子量: 224.213
• InChiKey: JAEFJAMYIRDNLT-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-亚甲基二氧基苯甲酰基甲酸乙酯 在 [RuCl(C₆H₆)(S)-SunPhos]Cl cerium(III) chloride 、 氢气 作用下， 以 乙醇 为溶剂， 50.0 ℃ 、5.0 MPa 条件下， 反应 20.0h， 生成 ethyl (2S)-2-(1,3-benzodioxol-5-yl)-2-hydroxyacetate 、 ethyl (2R)-2-(1,3-benzodioxol-5-yl)-2-hydroxyacetate
  参考文献：
  名称：

  CeCl₃·7H₂O: An Effective Additive in Ru-Catalyzed Enantioselective Hydrogenation of Aromatic α-Ketoesters

  摘要：

  In the presence of catalytic amounts of CeCl3 center dot 7H(2)O, [RuCl(benzene)(S)-SunPhos]Cl is a highly effective catalyst for the asymmetric hydrogenation of aromatic alpha-ketoesters. A variety of ethyl alpha-hydroxy-alpha-arylacetates have been prepared in up to 98.3% ee with a TON up to 10 000. Challenging aromatic alpha-ketoesters with ortho substituents are also hydrogenated with high enantioselectivities. The addition of CeCl3 center dot 7H(2)O not only improves the enantioselectivity but also enhances the stability of the catalyst. The ratio of CeCl3 center dot 7H(2)O to [RuCl(benzene)(S)-SunPhos]Cl plays an important role in the hydrogenation reaction with a large substrate/catalyst ratio.

  DOI：

  10.1021/jo800228e

文献信息

• CeCl₃·7H₂O: An Effective Additive in Ru-Catalyzed Enantioselective Hydrogenation of Aromatic α-Ketoesters
  作者：Qinghua Meng、Yanhui Sun、Virginie Ratovelomanana-Vidal、Jean Pierre Genêt、Zhaoguo Zhang

  DOI：10.1021/jo800228e

  日期：2008.5.1

  In the presence of catalytic amounts of CeCl3 center dot 7H(2)O, [RuCl(benzene)(S)-SunPhos]Cl is a highly effective catalyst for the asymmetric hydrogenation of aromatic alpha-ketoesters. A variety of ethyl alpha-hydroxy-alpha-arylacetates have been prepared in up to 98.3% ee with a TON up to 10 000. Challenging aromatic alpha-ketoesters with ortho substituents are also hydrogenated with high enantioselectivities. The addition of CeCl3 center dot 7H(2)O not only improves the enantioselectivity but also enhances the stability of the catalyst. The ratio of CeCl3 center dot 7H(2)O to [RuCl(benzene)(S)-SunPhos]Cl plays an important role in the hydrogenation reaction with a large substrate/catalyst ratio.