(4R,5S,2'R)-1,5-dimethyl-3-(1'-tert-butoxycarbonyl-2'-aziridinylcarbonyl)-4-phenylimidazolidin-2-one | 211575-58-5

• 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: (4R,5S,2'R)-1,5-dimethyl-3-(1'-tert-butoxycarbonyl-2'-aziridinylcarbonyl)-4-phenylimidazolidin-2-one
• 英文别名: tert-butyl (2R)-2-[(4S,5R)-3,4-dimethyl-2-oxo-5-phenylimidazolidine-1-carbonyl]aziridine-1-carboxylate
• CAS: 211575-58-5
• 化学式: C₁₉H₂₅N₃O₄
• 分子量: 359.425
• InChiKey: JKMCACFTGNWXGR-AVQMWMPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  69.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5S,2'R)-1,5-dimethyl-3-(1'-tert-butoxycarbonyl-2'-aziridinylcarbonyl)-4-phenylimidazolidin-2-one 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 甲苯 为溶剂， 反应 0.17h， 生成 (5R,4'R,5'S)-5-[(1',5'-Dimethyl-4'-phenylimidazolidin-2'-on-3'-yl)carbonyl]oxazolidin-2-one 、 (4R,4'R,5'S)-4-[(1',5'-Dimethyl-4'-phenylimidazolidin-2'-on-3'-yl)carbonyl]oxazolidin-2-one
  参考文献：
  名称：

  Cardillo; Gentilucci; Gianotti, Synlett, 2000, # 9, p. 1309 - 1311

  摘要：

  DOI：
• 作为产物：
  描述：

  tert-butyl (benzoyloxy)carbamate 在 sodium hydride lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 (4R,5S,2'R)-1,5-dimethyl-3-(1'-tert-butoxycarbonyl-2'-aziridinylcarbonyl)-4-phenylimidazolidin-2-one
  参考文献：
  名称：

  Diastereoselective synthesis of 3′-unsubstituted N-BOC-aziridine from a readily available chiral α,β-unsaturated imide

  摘要：

  The conjugate addition of N-BOC-O-benzoyl hydroxylamine catalysed by sodium hydride to a chiral cl,P-unsaturated imide gives a 3'-(BOC benzoyloxyaminopropanoyl) derivative. This undergoes cyclization upon treatment with sodium or lithium bases to give a 3'-unsubstituted N-BOC aziridine-2-imide in good yield and diastereoselectivity. When N-BOC..O-benzoyl hydroxylamine is deprotonated with stoichiometric lithium or sodium bases, the intermediate enolate resulting from the 1,4-addition spontaneously undergoes cyclization affording in a single step the N-BOC aziridine in higher yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00459-1

文献信息

• Diastereoselective synthesis of 3′-unsubstituted N-BOC-aziridine from a readily available chiral α,β-unsaturated imide
  作者：Giuliana Cardillo、Luca Gentilucci、Imma Ratera Bastardas、Alessandra Tolomelli

  DOI：10.1016/s0040-4020(98)00459-1

  日期：1998.7

  The conjugate addition of N-BOC-O-benzoyl hydroxylamine catalysed by sodium hydride to a chiral cl,P-unsaturated imide gives a 3'-(BOC benzoyloxyaminopropanoyl) derivative. This undergoes cyclization upon treatment with sodium or lithium bases to give a 3'-unsubstituted N-BOC aziridine-2-imide in good yield and diastereoselectivity. When N-BOC..O-benzoyl hydroxylamine is deprotonated with stoichiometric lithium or sodium bases, the intermediate enolate resulting from the 1,4-addition spontaneously undergoes cyclization affording in a single step the N-BOC aziridine in higher yield. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Cardillo; Gentilucci; Gianotti, Synlett, 2000, # 9, p. 1309 - 1311
  作者：Cardillo、Gentilucci、Gianotti、Tolomelli

  DOI：——

  日期：——