(4R)-N-benzyl-2,2-dibenzyl-4-diphenylphosphatoxy-5-methyl-5-nitrohexylamine | 615268-26-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (4R)-N-benzyl-2,2-dibenzyl-4-diphenylphosphatoxy-5-methyl-5-nitrohexylamine
• 英文别名: [(3R)-5,5-dibenzyl-6-(benzylamino)-2-methyl-2-nitrohexan-3-yl] diphenyl phosphate
• CAS: 615268-26-3
• 化学式: C₄₀H₄₃N₂O₆P
• 分子量: 678.765
• InChiKey: FXMJSEUXCJOIJU-KXQOOQHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  49
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4R)-N-benzyl-2,2-dibenzyl-4-diphenylphosphatoxy-5-methyl-5-nitrohexylamine 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 生成 (R)-1,4,4-tribenzyl-2-isopropyl-pyrrolidine 、 (S)-1,4,4-tribenzyl-2-isopropyl-pyrrolidine
  参考文献：
  名称：

  Enantioselective Cyclization of Alkene Radical Cations

  摘要：

  Enantiomerically enriched beta-(diphenylphosphatoxy)nitroalkanes undergo radical ionic fragmentation, induced by tributyltin hydride and AIBN in benzene at reflux, to give alkene radical cations in contact radical ion pairs. These contact ion pairs are trapped intramolecularly by amines to give pyrrolldines and piperidines with significant enantloselectivity (similar to60% ee), indicative of cyclization competing effectively with equilibration within the ion pairs. Use of an intramolecular N-propargylamine as a nucleophile provides an enantiomerically enriched pyrrolizidine skeleton via a tandem polar/radical crossover sequence.

  DOI：

  10.1021/ol035564x
• 作为产物：
  描述：

  ethyl 2-benzyl-3-phenylpropionate 在 lithium aluminium tetrahydride 、 草酰氯 、 (S)-(+)-alpha,alpha-二苯基脯氨醇 、 dimethyl sulfide borane 、 TEA 、 potassium tert-butylate 、 碘 、 sodium cyanoborohydride 、 臭氧 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 49.75h， 生成 (4R)-N-benzyl-2,2-dibenzyl-4-diphenylphosphatoxy-5-methyl-5-nitrohexylamine
  参考文献：
  名称：

  Enantioselective Cyclization of Alkene Radical Cations

  摘要：

  Enantiomerically enriched beta-(diphenylphosphatoxy)nitroalkanes undergo radical ionic fragmentation, induced by tributyltin hydride and AIBN in benzene at reflux, to give alkene radical cations in contact radical ion pairs. These contact ion pairs are trapped intramolecularly by amines to give pyrrolldines and piperidines with significant enantloselectivity (similar to60% ee), indicative of cyclization competing effectively with equilibration within the ion pairs. Use of an intramolecular N-propargylamine as a nucleophile provides an enantiomerically enriched pyrrolizidine skeleton via a tandem polar/radical crossover sequence.

  DOI：

  10.1021/ol035564x

文献信息

• Enantioselective Cyclization of Alkene Radical Cations
  作者：David Crich、Michio Shirai、Sochanchingwung Rumthao

  DOI：10.1021/ol035564x

  日期：2003.10.1

  Enantiomerically enriched beta-(diphenylphosphatoxy)nitroalkanes undergo radical ionic fragmentation, induced by tributyltin hydride and AIBN in benzene at reflux, to give alkene radical cations in contact radical ion pairs. These contact ion pairs are trapped intramolecularly by amines to give pyrrolldines and piperidines with significant enantloselectivity (similar to60% ee), indicative of cyclization competing effectively with equilibration within the ion pairs. Use of an intramolecular N-propargylamine as a nucleophile provides an enantiomerically enriched pyrrolizidine skeleton via a tandem polar/radical crossover sequence.