ethyl 3,5-dioxo-5-(pyrrolidin-1-yl)pentanoate | 1313990-78-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: ethyl 3,5-dioxo-5-(pyrrolidin-1-yl)pentanoate
• CAS: 1313990-78-1
• 化学式: C₁₁H₁₇NO₄
• 分子量: 227.26
• InChiKey: GUYXBDASOIJDOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.52
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 3,5-dioxo-5-(pyrrolidin-1-yl)pentanoate 在 [RuCl(benzene)(S)-SunPhos]Cl 、 氢气 作用下， 以 四氢呋喃 为溶剂， 70.0 ℃ 、2.0 MPa 条件下， 反应 15.0h， 生成 ethyl 3-hydroxy-5-oxo-5-(pyrrolidin-1-yl)pentanoate
  参考文献：
  名称：

  Ru-Catalyzed Asymmetric Hydrogenation of 3-Oxoglutaric Acid Derivatives via Solvent-Assisted Pinpoint Recognition of Carbonyls in Close Chemical Propinquity

  摘要：

  Upon comparison of hydrogenation rates of various beta-ketocarboxylic acid derivatives, beta-ketoamides were found to be hydrogenated slightly faster than beta-ketoesters in EtOH in the presence of [RuCl(benzene)(S)-SunPhos]Cl at 70 degrees C with 20 bar of hydrogen. In THF these differences were so sharpened that beta-ketoamides were hydrogenated even faster than In EtOH while the esters were extremely slow. Based on these findings, a series of 3-oxoglutaric acid derived with ester and amide moieties on the two ends were hydrogenated to 3-hydroxyl products with high enantioselectivities.

  DOI：

  10.1021/ol201406w
• 作为产物：
  描述：

  1,3-丙酮二羧酸二乙酯 在 氨 、 水 、 magnesium chloride 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 ethyl 3,5-dioxo-5-(pyrrolidin-1-yl)pentanoate
  参考文献：
  名称：

  Ru-Catalyzed Asymmetric Hydrogenation of 3-Oxoglutaric Acid Derivatives via Solvent-Assisted Pinpoint Recognition of Carbonyls in Close Chemical Propinquity

  摘要：

  Upon comparison of hydrogenation rates of various beta-ketocarboxylic acid derivatives, beta-ketoamides were found to be hydrogenated slightly faster than beta-ketoesters in EtOH in the presence of [RuCl(benzene)(S)-SunPhos]Cl at 70 degrees C with 20 bar of hydrogen. In THF these differences were so sharpened that beta-ketoamides were hydrogenated even faster than In EtOH while the esters were extremely slow. Based on these findings, a series of 3-oxoglutaric acid derived with ester and amide moieties on the two ends were hydrogenated to 3-hydroxyl products with high enantioselectivities.

  DOI：

  10.1021/ol201406w