(2S,3S)-tert-butyl-3-(4-chlorophenyl)-2-(diphenylmethyleneamino)-3-(1H-indol-3-yl)propanoate | 1221526-10-8

• 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: (2S,3S)-tert-butyl-3-(4-chlorophenyl)-2-(diphenylmethyleneamino)-3-(1H-indol-3-yl)propanoate
• 英文别名: tert-butyl (2S,3S)-2-(benzhydrylideneamino)-3-(4-chlorophenyl)-3-(1H-indol-3-yl)propanoate
• CAS: 1221526-10-8
• 化学式: C₃₄H₃₁ClN₂O₂
• 分子量: 535.085
• InChiKey: OTIQLHKAQPTFKL-CDZUIXILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (C8H6N)CH(Ts)(4-Cl-C6H4) 、 N-二苯亚甲基-甘氨酸叔丁酯 在 (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine 、 silver(I) chloride 、 caesium carbonate 作用下， 以 甲苯 为溶剂， 反应 24.08h， 以95%的产率得到(2S,3S)-tert-butyl-3-(4-chlorophenyl)-2-(diphenylmethyleneamino)-3-(1H-indol-3-yl)propanoate
  参考文献：
  名称：

  Ag-Catalyzed Diastereo- and Enantioselective Synthesis of β-Substituted Tryptophans from Sulfonylindoles

  摘要：

  The asymmetric catalytic synthesis of beta-substituted tryptophan derivatives was realized in high diastereo- and enantioselectivity by the reaction of glycine derivatives with sulfonylindoles in the presence of catalyst derived from AgCl and a commercially available chiral monodentate phosphoramidite ligand. The resulting adduct was readily converted to beta-substituted tryptophan in 95% overall yield for two steps, which presented a highly efficient route to chiral beta-substituted tryptophan.

  DOI：

  10.1021/ol100161n

文献信息

• Ag-Catalyzed Diastereo- and Enantioselective Synthesis of β-Substituted Tryptophans from Sulfonylindoles
  作者：Bao-Hui Zheng、Chang-Hua Ding、Xue-Long Hou、Li-Xin Dai

  DOI：10.1021/ol100161n

  日期：2010.4.16

  The asymmetric catalytic synthesis of beta-substituted tryptophan derivatives was realized in high diastereo- and enantioselectivity by the reaction of glycine derivatives with sulfonylindoles in the presence of catalyst derived from AgCl and a commercially available chiral monodentate phosphoramidite ligand. The resulting adduct was readily converted to beta-substituted tryptophan in 95% overall yield for two steps, which presented a highly efficient route to chiral beta-substituted tryptophan.