N-[(1S,2S)-2-(2-Benzyloxycarbonyl-2-methyl-propionylamino)-cyclohexyl]-2,2-dimethyl-malonamic acid benzyl ester | 910116-98-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[(1S,2S)-2-(2-Benzyloxycarbonyl-2-methyl-propionylamino)-cyclohexyl]-2,2-dimethyl-malonamic acid benzyl ester
• CAS: 910116-98-2
• 化学式: C₃₀H₃₈N₂O₆
• 分子量: 522.642
• InChiKey: CIPTWECSMQCJPB-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  38.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  110.8
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-[(1S,2S)-2-(2-Benzyloxycarbonyl-2-methyl-propionylamino)-cyclohexyl]-2,2-dimethyl-malonamic acid benzyl ester 在 palladium on activated charcoal 氢气 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 26.0h， 生成 N-[(2S)-1-hydroxy-3-methylbutan-2-yl]-N'-[(1S,2S)-2-[[3-[[(2S)-1-hydroxy-3-methylbutan-2-yl]amino]-2,2-dimethyl-3-oxopropanoyl]amino]cyclohexyl]-2,2-dimethylpropanediamide
  参考文献：
  名称：

  Synthesis and Crystallographic Characterization of Chiral Bis-oxazoline-amides. Fine-Tunable Ligands for Pd-Catalyzed Asymmetric Alkylations

  摘要：

  New chiral chelating C-2 bis-oxazoline-amide ligands (1) exhibiting a highly flexible molecular structure have been prepared in high yield through a versatile synthetic pathway. Combined crystallographic, variable temperature (VT)-NMR, IR, and ESI-MS studies have been carried out to investigate the nature of the 1-Pd complexes that are effective tools in controlling the stereochemical outcome of Pd-catalyzed allylic alkylations (ee up to 98%).

  DOI：

  10.1021/jo060767v
• 作为产物：
  描述：

  (1S,2S)-(+)-1,2-环己二胺 、 3-(benzyloxy)-2,2-dimethyl-3-oxopropanoic acid 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以43%的产率得到N-[(1S,2S)-2-(2-Benzyloxycarbonyl-2-methyl-propionylamino)-cyclohexyl]-2,2-dimethyl-malonamic acid benzyl ester
  参考文献：
  名称：

  Synthesis and Crystallographic Characterization of Chiral Bis-oxazoline-amides. Fine-Tunable Ligands for Pd-Catalyzed Asymmetric Alkylations

  摘要：

  New chiral chelating C-2 bis-oxazoline-amide ligands (1) exhibiting a highly flexible molecular structure have been prepared in high yield through a versatile synthetic pathway. Combined crystallographic, variable temperature (VT)-NMR, IR, and ESI-MS studies have been carried out to investigate the nature of the 1-Pd complexes that are effective tools in controlling the stereochemical outcome of Pd-catalyzed allylic alkylations (ee up to 98%).

  DOI：

  10.1021/jo060767v