16-[[4-[[7-(Naphthalen-2-ylmethyl)-1,4,7,10-tetrazacyclododec-1-yl]methyl]phenyl]methyl]-1,4,7,10,13-pentaoxa-16-azacyclooctadecane | 1380646-70-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 16-[[4-[[7-(Naphthalen-2-ylmethyl)-1,4,7,10-tetrazacyclododec-1-yl]methyl]phenyl]methyl]-1,4,7,10,13-pentaoxa-16-azacyclooctadecane
• CAS: 1380646-70-7
• 化学式: C₃₉H₅₉N₅O₅
• 分子量: 677.928
• InChiKey: KWAIPVFPEXWGDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  49
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  79.9
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  16-[[4-[[7-(Naphthalen-2-ylmethyl)-1,4,7,10-tetrazacyclododec-1-yl]methyl]phenyl]methyl]-1,4,7,10,13-pentaoxa-16-azacyclooctadecane 在 硝酸 作用下， 以 乙醚 、 乙醇 为溶剂， 以26%的产率得到
  参考文献：
  名称：

  Heteroditopic receptor based on crown ether and cyclen units for the recognition of zwitterionic amino acids

  摘要：

  The molecular recognition of five targeted amino acids differing in the nature of the side (R)- group and in the size of the aliphatic chain, glycine (Hgly), phenylalanine (Hphe), glutamic acid (Hglu(-)), 4-aminobutyric acid (Hgaba), and 6-aminohexanoic acid (Heahx), has been studied with a new heteroditopic receptor based in two distinct macrocycles, a cyclen and a crown ether moiety. The bismacrocycle L was synthesized via the bis-aminal route allowing to obtain the designed compound in gram scale and in good yield. Protonation constants of L and its binding constants with amino acids were determined by potentiometry in H2O/MeOH (1:1 v/v) solutions at 298.2 K and I=0.10 mol dm(-3) in NMe4NO3. Stronger binding ability of the HnLn+ receptor for a.-amino acids, Hgly and Hphen, than for the other studied substrates were found. Structural data derived from NMR studies showed that the binding of alpha-amino acids result from the cooperative participation of hydrogen bonds between the carboxylate group of amino acids and the polyammonium sites of cyclen, and the ion-dipole interactions between the ammonium group of the amino acids and the oxygen atoms of the crown ether. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.110
• 作为产物：
  描述：

  在 一水合肼 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 16-[[4-[[7-(Naphthalen-2-ylmethyl)-1,4,7,10-tetrazacyclododec-1-yl]methyl]phenyl]methyl]-1,4,7,10,13-pentaoxa-16-azacyclooctadecane
  参考文献：
  名称：

  Heteroditopic receptor based on crown ether and cyclen units for the recognition of zwitterionic amino acids

  摘要：

  The molecular recognition of five targeted amino acids differing in the nature of the side (R)- group and in the size of the aliphatic chain, glycine (Hgly), phenylalanine (Hphe), glutamic acid (Hglu(-)), 4-aminobutyric acid (Hgaba), and 6-aminohexanoic acid (Heahx), has been studied with a new heteroditopic receptor based in two distinct macrocycles, a cyclen and a crown ether moiety. The bismacrocycle L was synthesized via the bis-aminal route allowing to obtain the designed compound in gram scale and in good yield. Protonation constants of L and its binding constants with amino acids were determined by potentiometry in H2O/MeOH (1:1 v/v) solutions at 298.2 K and I=0.10 mol dm(-3) in NMe4NO3. Stronger binding ability of the HnLn+ receptor for a.-amino acids, Hgly and Hphen, than for the other studied substrates were found. Structural data derived from NMR studies showed that the binding of alpha-amino acids result from the cooperative participation of hydrogen bonds between the carboxylate group of amino acids and the polyammonium sites of cyclen, and the ion-dipole interactions between the ammonium group of the amino acids and the oxygen atoms of the crown ether. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.110