bis-[N-t-butyloxycarbonyl[2-(thien-2'-yl)benzoxazol-5-yl]-L-alanine methyl ester] | 1071443-42-9

• 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: bis-[N-t-butyloxycarbonyl[2-(thien-2'-yl)benzoxazol-5-yl]-L-alanine methyl ester]
• 英文别名: methyl (2S)-3-[2-[5-[5-[(2S)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]-1,3-benzoxazol-2-yl]thiophen-2-yl]-1,3-benzoxazol-5-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 1071443-42-9
• 化学式: C₃₆H₄₀N₄O₁₀S
• 分子量: 720.8
• InChiKey: SRYQXGJIUFIPSN-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  51
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  210
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  bis-[N-t-butyloxycarbonyl[2-(thien-2'-yl)benzoxazol-5-yl]-L-alanine methyl ester] 在 sodium hydroxide 、 potassium hydrogensulfate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 (2S)-3-[2-[5-[5-[(2S)-2-carboxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-1,3-benzoxazol-2-yl]thiophen-2-yl]-1,3-benzoxazol-5-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
  参考文献：
  名称：

  Synthesis, characterization, fluorescence and computational studies of new Cu2+, Ni2+ and Hg2+ complexes with emissive thienylbenzoxazolyl-alanine ligands

  摘要：

  The interaction of four fluorescent compounds containing thiophene and benzoxazole moieties combined with an alanine residue with alkaline, alkaline-earth, transition and post-transition metal ions was explored. The highly fluorescent heterocyclic alanine derivatives are strongly quenched in the solid state after complexation with the paramagnetic metal ions Cu2+ and Ni2+, and with the diamagnetic Hg2+. Absorption and steady-state fluorescence titrations reveal a selective interaction with Cu2+, Ni2+ and Hg2+. In all cases the formation of mononuclear or dinuclear metal complexes in solid state and in solution are postulated. DFT calculations on the mercury(II) complexes confirm the formation of dinuclear species. Our results suggest that one metal ion is coordinated by the chelate group formed by the amine and the protonated carboxylic groups present in the amino acid residue while a second metal ion is directly linked to the chromophore. As parent compound, L4 shows no interaction with Cu2+ and Ni2+ salts. However, the interaction with Hg2+ induces a strong quenching and a red shift of the fluorescence emission. (C) 2010 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2010.10.025
• 作为产物：
  描述：

  在 lead(IV) acetate 作用下， 以 二甲基亚砜 为溶剂， 反应 72.0h， 以0.19 g的产率得到bis-[N-t-butyloxycarbonyl[2-(thien-2'-yl)benzoxazol-5-yl]-L-alanine methyl ester]
  参考文献：
  名称：

  Synthesis and photophysical characterization of new fluorescent bis-amino acids bearing a heterocyclic bridge containing benzoxazole and thiophene

  摘要：

  A series of new bis-alanine derivatives bearing (oligo)thiophene and benzoxazole units as the hetero-aromatic bridge were synthesized in moderate to good yields. The photophysical characterization of these bis-amino acids was performed by UV-vis absorption and fluorescence emission studies and revealed that the compounds displayed exceptionally high fluorescence quantum yields, making them good candidates for application as fluorescent probes when incorporated into peptides, as well as peptide conformation-restricting and cross-linking elements. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.096