methyl (2R)-3-(4-hydroxyphenyl)-2-[2-(phenylmethoxycarbonylamino)ethylamino]propanoate | 828923-99-5

• 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: methyl (2R)-3-(4-hydroxyphenyl)-2-[2-(phenylmethoxycarbonylamino)ethylamino]propanoate
• CAS: 828923-99-5
• 化学式: C₂₀H₂₄N₂O₅
• 分子量: 372.421
• InChiKey: ICZAJZRCWBOPGF-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  27.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  96.89
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  二茂铁甲醇 、 methyl (2R)-3-(4-hydroxyphenyl)-2-[2-(phenylmethoxycarbonylamino)ethylamino]propanoate 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  A new ferrocene conjugate of a tyrosine PNA monomer: synthesis and electrochemical properties

  摘要：

  A new chiral ferrocene-labelled tyrosine PNA monomer I has been synthesised in good yield in both racemic and enantiomerically pure forms. It is suitable for insertion in various positions of PNA oligomers, a possibility that has been preliminarily demonstrated by synthesising the dimer 16. Moreover, in view of possible applications to nucleic acid detection, a preliminary voltarnmetric investigation on the electrochemical activity of monomer 1 and its synthetic precursors has been carried out in DMF. It appears that, despite the bulkiness of the PNA monomer backbone, its insertion on the ferrocene group only moderately lowers the latter's diffusion coefficients and peak currents, thus affording voltammetric detection limits in the order of 10(-6)-10(-7) M (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2004.09.049
• 作为产物：
  描述：

  N-(2-氧代乙基)氨基甲酸苄酯 、 D-酪氨酸甲酯 在 sodium cyanoborohydride 、 zinc(II) chloride 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 methyl (2R)-3-(4-hydroxyphenyl)-2-[2-(phenylmethoxycarbonylamino)ethylamino]propanoate
  参考文献：
  名称：

  A new ferrocene conjugate of a tyrosine PNA monomer: synthesis and electrochemical properties

  摘要：

  A new chiral ferrocene-labelled tyrosine PNA monomer I has been synthesised in good yield in both racemic and enantiomerically pure forms. It is suitable for insertion in various positions of PNA oligomers, a possibility that has been preliminarily demonstrated by synthesising the dimer 16. Moreover, in view of possible applications to nucleic acid detection, a preliminary voltarnmetric investigation on the electrochemical activity of monomer 1 and its synthetic precursors has been carried out in DMF. It appears that, despite the bulkiness of the PNA monomer backbone, its insertion on the ferrocene group only moderately lowers the latter's diffusion coefficients and peak currents, thus affording voltammetric detection limits in the order of 10(-6)-10(-7) M (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2004.09.049

文献信息

• A new ferrocene conjugate of a tyrosine PNA monomer: synthesis and electrochemical properties
  作者：Clara Baldoli、Luigi Falciola、Emanuela Licandro、Stefano Maiorana、Patrizia Mussini、Prasanna Ramani、Clara Rigamonti、Giovanna Zinzalla

  DOI：10.1016/j.jorganchem.2004.09.049

  日期：2004.12

  A new chiral ferrocene-labelled tyrosine PNA monomer I has been synthesised in good yield in both racemic and enantiomerically pure forms. It is suitable for insertion in various positions of PNA oligomers, a possibility that has been preliminarily demonstrated by synthesising the dimer 16. Moreover, in view of possible applications to nucleic acid detection, a preliminary voltarnmetric investigation on the electrochemical activity of monomer 1 and its synthetic precursors has been carried out in DMF. It appears that, despite the bulkiness of the PNA monomer backbone, its insertion on the ferrocene group only moderately lowers the latter's diffusion coefficients and peak currents, thus affording voltammetric detection limits in the order of 10(-6)-10(-7) M (C) 2004 Elsevier B.V. All rights reserved.