(2S)-N-[(1S)-2-hydroxy-1-phenyl-ethyl]-5-oxo-pyrrolidine-2-carboxamide | 1240160-38-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-N-[(1S)-2-hydroxy-1-phenyl-ethyl]-5-oxo-pyrrolidine-2-carboxamide
• 英文别名: (2S)-N-[(1R)-2-hydroxy-1-phenylethyl]-5-oxopyrrolidine-2-carboxamide
• CAS: 1240160-38-6
• 化学式: C₁₃H₁₆N₂O₃
• 分子量: 248.282
• InChiKey: XHXAZNNIIXZJLY-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  D-苯甘氨醇 、 L-焦谷氨酸甲酯 在 1,5,7-三氮杂双环[4.4.0]癸-5-烯 作用下， 以70%的产率得到(2S)-N-[(1S)-2-hydroxy-1-phenyl-ethyl]-5-oxo-pyrrolidine-2-carboxamide
  参考文献：
  名称：

  Pyroglutamate-derived hydroxyamide ligands: synthesis and application to asymmetric catalysis

  摘要：

  The synthesis of a series of chiral hydroxy amide ligands is described These ligands were used in a ruthenium-catalysed transfer hydrogenation reaction where one ligand gave the product in 72% ee. The ligands were also used in two titanium-catalysed reactions, an alkylation where ee's of up to 74% were achieved and a phenyl acetylene addition where more modest selectivities were observed (C) 2010 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.tetasy.2010.04.055
• 作为试剂：
  描述：

  diethylzinc 、 苯甲醛 在 titanium(IV) isopropylate 、 (2S)-N-[(1S)-2-hydroxy-1-phenyl-ethyl]-5-oxo-pyrrolidine-2-carboxamide 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 18.5h， 生成 (R)-(+)-1-苯基-1-丙醇 、 S(-)-1-苯基-1-丙醇
  参考文献：
  名称：

  Pyroglutamate-derived hydroxyamide ligands: synthesis and application to asymmetric catalysis

  摘要：

  The synthesis of a series of chiral hydroxy amide ligands is described These ligands were used in a ruthenium-catalysed transfer hydrogenation reaction where one ligand gave the product in 72% ee. The ligands were also used in two titanium-catalysed reactions, an alkylation where ee's of up to 74% were achieved and a phenyl acetylene addition where more modest selectivities were observed (C) 2010 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.tetasy.2010.04.055

文献信息

• Pyroglutamate-derived hydroxyamide ligands: synthesis and application to asymmetric catalysis
  作者：Paul Geoghegan、Patrick O’Leary

  DOI：10.1016/j.tetasy.2010.04.055

  日期：2010.4

  The synthesis of a series of chiral hydroxy amide ligands is described These ligands were used in a ruthenium-catalysed transfer hydrogenation reaction where one ligand gave the product in 72% ee. The ligands were also used in two titanium-catalysed reactions, an alkylation where ee's of up to 74% were achieved and a phenyl acetylene addition where more modest selectivities were observed (C) 2010 Elsevier Ltd. All rights reserved