benzhydryl 3-hydroxybutanoate | 1313990-75-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzhydryl 3-hydroxybutanoate
• CAS: 1313990-75-8
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: QPZOQNTXXDEOOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  benzhydryl 3-hydroxybutanoate 、 丙酸酐 在 potassium carbonate 、 四米唑 作用下， 以 异丙醚 为溶剂， 生成 benzhydryl 3-(propionyloxy)butanoate
  参考文献：
  名称：

  Kinetic Resolution of α-Methylene-β-hydroxy Esters Catalyzed by Acyl Transfer Catalyst An-PIQ

  摘要：

  A highly efficient nonenzymatic kinetic resolution of a series of structurally diverse racemic alpha-methylene-beta-hydroxy esters utilizing the acyl transfer catalyst An-PIQ and propionic anhydride is reported. This procedure provides recovered alcohols with extremely high ees (up to >99%) in reasonable conversions and excellent selectivity factors (S up to 108). Several synthetically important substrates were resolved in gram-scale reactions, and highly optically pure alpha-methylene-beta-hydroxy esters were obtained with excellent S values and good yields.

  DOI：

  10.1021/acs.joc.5b00073
• 作为产物：
  描述：

  diphenylmethyl 3-oxobutanoate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.25h， 生成 benzhydryl 3-hydroxybutanoate
  参考文献：
  名称：

  Kinetic Resolution of α-Methylene-β-hydroxy Esters Catalyzed by Acyl Transfer Catalyst An-PIQ

  摘要：

  A highly efficient nonenzymatic kinetic resolution of a series of structurally diverse racemic alpha-methylene-beta-hydroxy esters utilizing the acyl transfer catalyst An-PIQ and propionic anhydride is reported. This procedure provides recovered alcohols with extremely high ees (up to >99%) in reasonable conversions and excellent selectivity factors (S up to 108). Several synthetically important substrates were resolved in gram-scale reactions, and highly optically pure alpha-methylene-beta-hydroxy esters were obtained with excellent S values and good yields.

  DOI：

  10.1021/acs.joc.5b00073

文献信息

• Ru-Catalyzed Asymmetric Hydrogenation of 3-Oxoglutaric Acid Derivatives via Solvent-Assisted Pinpoint Recognition of Carbonyls in Close Chemical Propinquity
  作者：Wanfang Li、Xin Ma、Weizheng Fan、Xiaoming Tao、Xiaoming Li、Xiaomin Xie、Zhaoguo Zhang

  DOI：10.1021/ol201406w

  日期：2011.8.5

  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.