25,26,27,28,29-Pentaazahexacyclo[20.2.1.12,5.17,10.112,15.117,20]nonacosa-1,3,5,7(28),8,10,12,14,16,18,20(26),21,23-tridecaene-9,18-diaceticacid, 4,13,14,23-tetraethyl-3,8,19,24-tetramethyl- | 125735-80-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: 25,26,27,28,29-Pentaazahexacyclo[20.2.1.12,5.17,10.112,15.117,20]nonacosa-1,3,5,7(28),8,10,12,14,16,18,20(26),21,23-tridecaene-9,18-diaceticacid, 4,13,14,23-tetraethyl-3,8,19,24-tetramethyl-
• CAS: 125735-80-0；133179-29-0
• 化学式: C₄₀H₄₅N₅O₄
• 分子量: 659.828
• InChiKey: BANBSMUEYMRQOC-KMRPMRTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.04
• 重原子数：
  49.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  147.75
• 氢给体数：
  5.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  25,26,27,28,29-Pentaazahexacyclo[20.2.1.12,5.17,10.112,15.117,20]nonacosa-1,3,5,7(28),8,10,12,14,16,18,20(26),21,23-tridecaene-9,18-diaceticacid, 4,13,14,23-tetraethyl-3,8,19,24-tetramethyl- 、 L-苯丙氨酸叔丁酯盐酸盐 在 吡啶 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以67%的产率得到
  参考文献：
  名称：

  Efficient Transport of Aromatic Amino Acids by Sapphyrin-Lasalocid Conjugates

  摘要：

  The synthesis and characterization of several sapphyrin-lasalocid conjugates is reported. This family of receptors is capable of acting as efficient and selective carriers for aromatic alpha-amino acids, as judged from both U-tube and W-tube through-model-membrane transport experiments. The first member of this family, system 6, was found to display an inherent preference for phenylalanine > tryptophan > tyrosine. Further, L-amino acids were shown to be transported with greater efficiency than the corresponding D-enantiomers by this particular carrier. The high level of amino acid carrier capability displayed by receptor 6 in dichloromethane solutions correlates well with the results of equilibrium binding studies carried out using visible-spectroscopic titrations. These latter studies revealed that system 6 does display significant affinity for zwitterionic amino acids in this organic solvent. These binding studies, as well as a number of control experiments involving, inter alia, porphyrin-lasalocid conjugate 7, showed the importance of having both the sapphyrin and lasalocid subunits contained within the same overall receptor framework. The four other second-generation sapphyrin-lasalocid conjugates reported here (11-14) were also tested as carriers for the transport of Phe, Trp, and Tyr. It was found that the esterified systems 11 and 12 functioned well as amino acid carriers, while the free-acid compounds 13 and 14 did not. These latter conjugates, containing both carboxylic acid and sapphyrin subunits, presumably undergo self-assembly in organic solutions, a process that hampers their ability to act as effective carriers. In the case of the functioning systems 11 and 12, the configuration of the stereogenic phenylalanine appendages could be varied such that either the L- or D-antipodes of the aromatic amino acid substrates being studied were transported al a greater rate.

  DOI：

  10.1002/(sici)1521-3765(199801)4:1<159::aid-chem159>3.0.co;2-n
• 作为产物：
  描述：

  3,3'-dimethyl-4,4'-diethyl-2,2'-bipyrrole 在 氢氧化钾 、 氧气 、 对甲苯磺酸 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 生成 25,26,27,28,29-Pentaazahexacyclo[20.2.1.12,5.17,10.112,15.117,20]nonacosa-1,3,5,7(28),8,10,12,14,16,18,20(26),21,23-tridecaene-9,18-diaceticacid, 4,13,14,23-tetraethyl-3,8,19,24-tetramethyl-
  参考文献：
  名称：

  Sessler, Jonathan L.; Cyr, Michael J.; Lynch, Vincent, Journal of the American Chemical Society, 1990, vol. 112, # 7, p. 2810 - 2813

  摘要：

  DOI：