(2R,3R)-2,3-bis(benzoyloxy)succinic acid mono-((S)-2-isopropyl-2,3-dimethyl-4-oxo-imidazolidin-1-yl) ester | 1337525-29-7

• 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: (2R,3R)-2,3-bis(benzoyloxy)succinic acid mono-((S)-2-isopropyl-2,3-dimethyl-4-oxo-imidazolidin-1-yl) ester
• CAS: 1337525-29-7
• 化学式: C₂₆H₂₈N₂O₉
• 分子量: 512.516
• InChiKey: QTWBFDIZODZJAB-YPCDYVTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  37.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  139.75
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2,3-bis(benzoyloxy)succinic acid mono-((S)-2-isopropyl-2,3-dimethyl-4-oxo-imidazolidin-1-yl) ester 在 双氧水 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 0.33h， 以57%的产率得到2-isopropyl-1,2-dimethyl-5-oxo-2,5-dihydro-1H-imidazole 3-oxide
  参考文献：
  名称：

  Inexpensive, multigram-scale preparation of an enantiopure cyclic nitrone via resolution at the hydroxylamine stage

  摘要：

  The reduction of the chiral, racemic nitrone MiPNO provides a secondary hydroxylamine. Its O-acylation with O,O'-dibenzoyl-L-tartaric acid anhydride gives two diastereomers, that can be easily separated by selective dissolution in orthogonal solvents. The recovery of the enantiopure nitrone is then carried out in a single step. The process allows the straightforward isolation of (R) and (S)-MiPNO in 57% and 38% yield, respectively, from rac-MiPNO. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.07.002
• 作为产物：
  描述：

  2-isopropyl-1,2-dimethyl-5-oxo-2,5-dihydro-1H-imidazole 3-oxide 在 4-二甲氨基吡啶 、 dimethyl sulfide borane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.83h， 生成 (2R,3R)-2,3-bis(benzoyloxy)succinic acid mono-((S)-2-isopropyl-2,3-dimethyl-4-oxo-imidazolidin-1-yl) ester
  参考文献：
  名称：

  Inexpensive, multigram-scale preparation of an enantiopure cyclic nitrone via resolution at the hydroxylamine stage

  摘要：

  The reduction of the chiral, racemic nitrone MiPNO provides a secondary hydroxylamine. Its O-acylation with O,O'-dibenzoyl-L-tartaric acid anhydride gives two diastereomers, that can be easily separated by selective dissolution in orthogonal solvents. The recovery of the enantiopure nitrone is then carried out in a single step. The process allows the straightforward isolation of (R) and (S)-MiPNO in 57% and 38% yield, respectively, from rac-MiPNO. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.07.002