(4R,5S)-1,5-dimethyl-3-(3'-N-tert-butoxycarbonylbenzoyloxyaminopropanoyl)-4-phenylimidazolidin-2-one | 211575-56-3

• 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: (4R,5S)-1,5-dimethyl-3-(3'-N-tert-butoxycarbonylbenzoyloxyaminopropanoyl)-4-phenylimidazolidin-2-one
• 英文别名: [[3-[(4S,5R)-3,4-dimethyl-2-oxo-5-phenylimidazolidin-1-yl]-3-oxopropyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino] benzoate
• CAS: 211575-56-3
• 化学式: C₂₆H₃₁N₃O₆
• 分子量: 481.549
• InChiKey: FIZMEINSEKGTRT-AVRDEDQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  96.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R,5S)-1,5-dimethyl-3-(3'-N-tert-butoxycarbonylbenzoyloxyaminopropanoyl)-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 0.75h， 以90%的产率得到(4R,5S,2'S)-1,5-dimethyl-3-(2'phenylcarbonyl-3'-N-tert-butoxycarbonylhydroxyaminopropanoyl)-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
• 作为产物：
  描述：

  tert-butyl (benzoyloxy)carbamate 、 (4R,5S)-1,5-dimethyl-4-phenyl-3-(2-propenoyl)-2-imidazolidinone 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以85%的产率得到(4R,5S)-1,5-dimethyl-3-(3'-N-tert-butoxycarbonylbenzoyloxyaminopropanoyl)-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.