Ethyl 2-[[5,11,17,23-tetratert-butyl-27-(2-ethoxy-2-oxoethoxy)-26,28-bis[[1-(pyren-1-ylmethyl)triazol-4-yl]methoxy]-2,8,14,20-tetrathiapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaen-25-yl]oxy]acetate | 1309130-55-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: Ethyl 2-[[5,11,17,23-tetratert-butyl-27-(2-ethoxy-2-oxoethoxy)-26,28-bis[[1-(pyren-1-ylmethyl)triazol-4-yl]methoxy]-2,8,14,20-tetrathiapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaen-25-yl]oxy]acetate
• 英文别名: ethyl 2-[[5,11,17,23-tetratert-butyl-27-(2-ethoxy-2-oxoethoxy)-26,28-bis[[1-(pyren-1-ylmethyl)triazol-4-yl]methoxy]-2,8,14,20-tetrathiapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaen-25-yl]oxy]acetate
• CAS: 1309130-55-9
• 化学式: C₈₈H₈₆N₆O₈S₄
• 分子量: 1483.95
• InChiKey: XJRPEKZKQVEDQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  23.4
• 重原子数：
  106
• 可旋转键数：
  24
• 环数：
  15.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  252
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  Ethyl 2-[[5,11,17,23-tetratert-butyl-27-(2-ethoxy-2-oxoethoxy)-26,28-bis[[1-(pyren-1-ylmethyl)triazol-4-yl]methoxy]-2,8,14,20-tetrathiapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaen-25-yl]oxy]acetate 在 一水合肼 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 以86%的产率得到
  参考文献：
  名称：

  Positive allosteric binding behavior of pyrene-appended triazole-modified thiacalix[4]arene-based fluorescent receptors

  摘要：

  The novel heteroditopic receptors 5(a similar to c) have been synthesized, which bear a thiacalix[4]arene in the 1,3-alternate conformation. Two urea moieties possessing various aryl groups with either electron-donating or -withdrawing groups at their p-positions function as anion-binding sites. At the opposite side of the cavity are two pyrene-appended triazole rings, which act as cation-binding sites. The binding property of receptor 5(c) was investigated by means of H-1 NMR and UV-vis spectroscopy and by fluorescence titration experiments in the presence of various transition metal cations and anions in CH2Cl2-DMSO (10:1, v/v) solution. Interestingly, it was found that receptor 5(c) possessing two p-nitrophenyl ureido moieties, most efficiently complexes in the urea cavity or bistriazoles; the plausible allosteric effect of receptor 5(c) was also investigated. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.08.068
• 作为产物：
  描述：

  、 1-(叠氮基甲基)芘 在 copper(l) iodide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以73%的产率得到Ethyl 2-[[5,11,17,23-tetratert-butyl-27-(2-ethoxy-2-oxoethoxy)-26,28-bis[[1-(pyren-1-ylmethyl)triazol-4-yl]methoxy]-2,8,14,20-tetrathiapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaen-25-yl]oxy]acetate
  参考文献：
  名称：

  Synthesis and evaluation of a novel pyrenyl-appended triazole-based thiacalix[4]arene as a fluorescent sensor for Ag+ ion

  摘要：

  New fluorescent chemosensors 1,3-alternate-1 and 2 with pyrenyl-appended triazole-based on thiacalix[4]arene were synthesized. The fluorescence spectra changes suggested that chemosensors 1 and 2 are highly selective for Ag+ over other metal ions by enhancing the monomer emission of pyrene in neutral solution. However, other heavy metal ions, such as Cu2+, and Hg2+ quench both the monomer and excimer emission of pyrene acutely. The H-1 NMR results indicated that Ag+ can be selectively recognized by the triazole moieties on the receptors 1 and 2 together with the ionophoricity cavity formed by the two inverted benzene rings and sulfur atoms of the thiacalix[4]arene. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.008

文献信息

• Synthesis and evaluation of a novel pyrenyl-appended triazole-based thiacalix[4]arene as a fluorescent sensor for Ag+ ion
  作者：Xin-Long Ni、Xi Zeng、Carl Redshaw、Takehiko Yamato

  DOI：10.1016/j.tet.2011.03.008

  日期：2011.5

  New fluorescent chemosensors 1,3-alternate-1 and 2 with pyrenyl-appended triazole-based on thiacalix[4]arene were synthesized. The fluorescence spectra changes suggested that chemosensors 1 and 2 are highly selective for Ag+ over other metal ions by enhancing the monomer emission of pyrene in neutral solution. However, other heavy metal ions, such as Cu2+, and Hg2+ quench both the monomer and excimer emission of pyrene acutely. The H-1 NMR results indicated that Ag+ can be selectively recognized by the triazole moieties on the receptors 1 and 2 together with the ionophoricity cavity formed by the two inverted benzene rings and sulfur atoms of the thiacalix[4]arene. (C) 2011 Elsevier Ltd. All rights reserved.
• Positive allosteric binding behavior of pyrene-appended triazole-modified thiacalix[4]arene-based fluorescent receptors
  作者：Hirotsugu Tomiyasu、Naoki Shigyo、Xin-Long Ni、Xi Zeng、Carl Redshaw、Takehiko Yamato

  DOI：10.1016/j.tet.2014.08.068

  日期：2014.10

  The novel heteroditopic receptors 5(a similar to c) have been synthesized, which bear a thiacalix[4]arene in the 1,3-alternate conformation. Two urea moieties possessing various aryl groups with either electron-donating or -withdrawing groups at their p-positions function as anion-binding sites. At the opposite side of the cavity are two pyrene-appended triazole rings, which act as cation-binding sites. The binding property of receptor 5(c) was investigated by means of H-1 NMR and UV-vis spectroscopy and by fluorescence titration experiments in the presence of various transition metal cations and anions in CH2Cl2-DMSO (10:1, v/v) solution. Interestingly, it was found that receptor 5(c) possessing two p-nitrophenyl ureido moieties, most efficiently complexes in the urea cavity or bistriazoles; the plausible allosteric effect of receptor 5(c) was also investigated. (C) 2014 Elsevier Ltd. All rights reserved.