methyl 1-[(1-benzyl-5-oxopyrrolidine-2(S)-carbonyloxy)acetyl]-2-oxoimidazolidine-4(S)-carboxylate | 459454-30-9

• 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: methyl 1-[(1-benzyl-5-oxopyrrolidine-2(S)-carbonyloxy)acetyl]-2-oxoimidazolidine-4(S)-carboxylate
• 英文别名: Methyl 1-[(1-benzyl-5-oxopyrrolidine-2(s)-carbonyl-oxy)acetyl]-2-oxoimidazolidine-4(s)-carboxylate；methyl (4S)-1-[2-[(2S)-1-benzyl-5-oxopyrrolidine-2-carbonyl]oxyacetyl]-2-oxoimidazolidine-4-carboxylate
• CAS: 459454-30-9
• 化学式: C₁₉H₂₁N₃O₇
• 分子量: 403.392
• InChiKey: MKHDGBCIEWUFTI-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  rhodium(II) acetate dimer 、 methyl 1-[(1-benzyl-5-oxopyrrolidine-2(S)-carbonyloxy)acetyl]-2-oxoimidazolidine-4(S)-carboxylate 以 氯苯 为溶剂， 以55%的产率得到dirhodium(II) tetrakis[methyl 1-[(1-benzyl-5-oxopyrrolidine-2(S)-carbonyloxy)acetyl]-2-oxoimidazolidine-4(S)-carboxylate]
  参考文献：
  名称：

  摘要：

  Chiral attachments on 2-oxoimidazolidine-4(S)-carboxylate ligands for dirhodium(11) can provide differential diastereoselection in catalytic reactions of diazo compounds. The synthesis of these heterocyclic ligands from the readily available amino acid asparagine is reported. Reactions with diazoacetates offering intramolecular carbon-hydrogen insertion provide evaluative data that demonstrate differential diastereoselection. Surprisingly, placement of a carbonyl group within the chiral attachment remove, enantiocontrol from the catalyst, presumably because of intramolecular ylide formation.

  DOI：

  10.1023/a:1015061620557
• 作为产物：
  描述：

  methyl 3-benzyloxycarbonyl-1-bromoacetyl-2-oxoimidazolidine-4(S)-carboxylate 在 palladium on activated charcoal 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙酸乙酯 、 苯 为溶剂， 反应 1.0h， 生成 methyl 1-[(1-benzyl-5-oxopyrrolidine-2(S)-carbonyloxy)acetyl]-2-oxoimidazolidine-4(S)-carboxylate
  参考文献：
  名称：

  摘要：

  Chiral attachments on 2-oxoimidazolidine-4(S)-carboxylate ligands for dirhodium(11) can provide differential diastereoselection in catalytic reactions of diazo compounds. The synthesis of these heterocyclic ligands from the readily available amino acid asparagine is reported. Reactions with diazoacetates offering intramolecular carbon-hydrogen insertion provide evaluative data that demonstrate differential diastereoselection. Surprisingly, placement of a carbonyl group within the chiral attachment remove, enantiocontrol from the catalyst, presumably because of intramolecular ylide formation.

  DOI：

  10.1023/a:1015061620557