methyl (Z)-2-(benzyloxycarbonyl)amino-3-[(1-t-butoxycarbonyl-2-phenyl)indol-3-yl]acrylate | 484014-15-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl (Z)-2-(benzyloxycarbonyl)amino-3-[(1-t-butoxycarbonyl-2-phenyl)indol-3-yl]acrylate
• CAS: 484014-15-5
• 化学式: C₃₁H₃₀N₂O₆
• 分子量: 526.589
• InChiKey: MLDPRNJTHQFHLL-PLRJNAJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.53
• 重原子数：
  39.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  95.86
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl (Z)-2-(benzyloxycarbonyl)amino-3-[(1-t-butoxycarbonyl-2-phenyl)indol-3-yl]acrylate 在 1,2-bis[(2S,5S)-2,5-diethylphospholano]benzene(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate 氢气 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 (S)-N^α-benzyloxycarbonyl-1-(1-t-butoxycarbonyl-2-phenyl)tryptophan methyl ester 、 (R)-N^α-benzyloxycarbonyl-1-(1-t-butoxycarbonyl-2-phenyl)tryptophan methyl ester
  参考文献：
  名称：

  Design and synthesis of novel χ2-constrained phenylalanine, naphthylalanine, and tryptophan analogues and their use in biologically active melanotropin peptides

  摘要：

  A series of novel hydrophobic, bulky chi(2)-constrained phenylalanine, naphthylalanine, and tryptophan derivatives was designed and synthesized. The key steps involved asymmetric hydrogenations of alpha-enamides using Burk's DuPHOS-based Rh(l) catalysts to give high enantiomerically pure alpha-amino acid derivatives. The subsequent Suzuki cross couplings of the amino acid analogues with boronic acid derivatives afforded these aromatic substituted amino acids in high yields and with high enantioselectivity. The incorporation of these novel chi(2)-constrained amino acids into peptides and peptidomimetics provides fruitful information in the development of peptide and peptidomimetic ligands of melanotropins and an understanding of the interactions between ligands and receptors/acceptors. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00588-4
• 作为产物：
  描述：

  2-苯基吲哚-3-甲醛 在 吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 生成 methyl (Z)-2-(benzyloxycarbonyl)amino-3-[(1-t-butoxycarbonyl-2-phenyl)indol-3-yl]acrylate
  参考文献：
  名称：

  Design and synthesis of novel χ2-constrained phenylalanine, naphthylalanine, and tryptophan analogues and their use in biologically active melanotropin peptides

  摘要：

  A series of novel hydrophobic, bulky chi(2)-constrained phenylalanine, naphthylalanine, and tryptophan derivatives was designed and synthesized. The key steps involved asymmetric hydrogenations of alpha-enamides using Burk's DuPHOS-based Rh(l) catalysts to give high enantiomerically pure alpha-amino acid derivatives. The subsequent Suzuki cross couplings of the amino acid analogues with boronic acid derivatives afforded these aromatic substituted amino acids in high yields and with high enantioselectivity. The incorporation of these novel chi(2)-constrained amino acids into peptides and peptidomimetics provides fruitful information in the development of peptide and peptidomimetic ligands of melanotropins and an understanding of the interactions between ligands and receptors/acceptors. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00588-4