(4S,5R,2'R,3'S)-1,5-dimethyl-4-phenyl-3-[(2'-N-benzoyl-aziridinyl-3'-isopropyl)carbonyl]-imidazolidin-2-one | 347885-22-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S,5R,2'R,3'S)-1,5-dimethyl-4-phenyl-3-[(2'-N-benzoyl-aziridinyl-3'-isopropyl)carbonyl]-imidazolidin-2-one
• 英文别名: (4R,5S)-1-[(2R,3S)-1-benzoyl-3-propan-2-ylaziridine-2-carbonyl]-3,4-dimethyl-5-phenylimidazolidin-2-one
• CAS: 347885-22-7
• 化学式: C₂₄H₂₇N₃O₃
• 分子量: 405.497
• InChiKey: FLICEPMDUAQSSU-DHEFTLAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  60.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5R,2'R,3'S)-1,5-dimethyl-4-phenyl-3-[(2'-N-benzoyl-aziridinyl-3'-isopropyl)carbonyl]-imidazolidin-2-one 在 lithium hydroxide 、 三氟化硼乙醚 、 双氧水 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (4R,5S)-5-isopropyl-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid
  参考文献：
  名称：

  Asymmetric synthesis of 5-isopropyl-oxazoline-4-imide as syn-hydroxyleucine precursor

  摘要：

  The synthesis of syn N-acetyl-hydroxyleucine methyl ester is reported through the ring expansion of aziridine-2-imides to oxazoline-4-imides. The key steps of the synthesis are the I,il-addition of O-benzylhydroxylamine to unsaturated imides, promoted by Lewis acids, and the regio- and stereoselective ring expansion of ti ans-aziridines to trans-oxazolines. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00084-2
• 作为产物：
  描述：

  (4S,5R)-3-(3'-benzyloxylamino-4'-methylpentanoyl)-1,5-dimethyl-4-phenylimidazolidin-2-one 在 二甲基氯化铝 、 三乙胺 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 5.33h， 生成 (4S,5R,2'R,3'S)-1,5-dimethyl-4-phenyl-3-[(2'-N-benzoyl-aziridinyl-3'-isopropyl)carbonyl]-imidazolidin-2-one
  参考文献：
  名称：

  Asymmetric synthesis of 5-isopropyl-oxazoline-4-imide as syn-hydroxyleucine precursor

  摘要：

  The synthesis of syn N-acetyl-hydroxyleucine methyl ester is reported through the ring expansion of aziridine-2-imides to oxazoline-4-imides. The key steps of the synthesis are the I,il-addition of O-benzylhydroxylamine to unsaturated imides, promoted by Lewis acids, and the regio- and stereoselective ring expansion of ti ans-aziridines to trans-oxazolines. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00084-2