(R)-N^α-benzyloxycarbonyl-o-bromonaphthylalanine methyl ester | 445417-44-7

• 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: (R)-N^α-benzyloxycarbonyl-o-bromonaphthylalanine methyl ester
• 英文别名: (R)-N^α-benzyloxycarbonyl-(1-bromo-2-napthyl)alanine methyl ester；methyl (2R)-3-(1-bromonaphthalen-2-yl)-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 445417-44-7
• 化学式: C₂₂H₂₀BrNO₄
• 分子量: 442.309
• InChiKey: GXJBOWCNWMNISK-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-萘硼酸 、 (R)-N^α-benzyloxycarbonyl-o-bromonaphthylalanine methyl ester 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 水 、 苯 为溶剂， 反应 36.0h， 以100%的产率得到(R)-N^α-benzyloxycarbonyl-[1-(1-naphthyl)-2-naphthyl]alanine methyl ester
  参考文献：
  名称：

  Design and synthesis of hydrophobic, bulky χ2-constrained phenylalanine and naphthylalanine derivatives

  摘要：

  A series of novel hydrophobic, bulky chi(2)-constrained phenylalanine and naphthylalanine derivatives were designed and synthesized. Asymmetric hydrogenations of alpha-enamides using Burk's DuPHOS-based Rh(I) catalysts generated high enantiomerically pure alpha-amino acid derivatives, which subsequently underwent Suzuki cross couplings with boronic acid derivatives to afford these aromatic Substituted amino acids in high yields and with high enantioselectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00249-6
• 作为产物：
  描述：

  1-溴-2-萘甲醛 在 (-)-1,2-bis-((2R,5R)-2,5-diethylphospholano)benzene(cyclooctadiene) rhodium(I) trifluoromethanesulfonate 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、448.16 kPa 条件下， 反应 29.0h， 生成 (R)-N^α-benzyloxycarbonyl-o-bromonaphthylalanine 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

文献信息

• Design and synthesis of novel χ2-constrained phenylalanine, naphthylalanine, and tryptophan analogues and their use in biologically active melanotropin peptides
  作者：Wei Wang、Minying Cai、Chiyi Xiong、Junyi Zhang、Dev Trivedi、Victor J Hruby

  DOI：10.1016/s0040-4020(02)00588-4

  日期：2002.9

  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.
• Design and synthesis of hydrophobic, bulky χ2-constrained phenylalanine and naphthylalanine derivatives
  作者：Wei Wang、Junyi Zhang、Chiyi Xiong、Victor J. Hruby

  DOI：10.1016/s0040-4039(02)00249-6

  日期：2002.3

  A series of novel hydrophobic, bulky chi(2)-constrained phenylalanine and naphthylalanine derivatives were designed and synthesized. Asymmetric hydrogenations of alpha-enamides using Burk's DuPHOS-based Rh(I) catalysts generated high enantiomerically pure alpha-amino acid derivatives, which subsequently underwent Suzuki cross couplings with boronic acid derivatives to afford these aromatic Substituted amino acids in high yields and with high enantioselectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.