5-[3-(3-tert-butoxycarbonylaminopropionylamino)phenyl]-17-(3-nitrophenyl)-25,27-bis(methoxycarbonylmethoxy)calix[4]arene-26,28-diol | 514204-33-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-[3-(3-tert-butoxycarbonylaminopropionylamino)phenyl]-17-(3-nitrophenyl)-25,27-bis(methoxycarbonylmethoxy)calix[4]arene-26,28-diol
• 英文别名: Methyl 2-[[26,28-dihydroxy-27-(2-methoxy-2-oxoethoxy)-5-[3-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoylamino]phenyl]-17-(3-nitrophenyl)-25-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9(27),10,12,15(26),16,18,21,23-dodecaenyl]oxy]acetate
• CAS: 514204-33-2
• 化学式: C₅₄H₅₃N₃O₁₃
• 分子量: 952.027
• InChiKey: ZGJXKGXHDZJZGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  70
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  225
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  5-[3-(3-tert-butoxycarbonylaminopropionylamino)phenyl]-17-(3-nitrophenyl)-25,27-bis(methoxycarbonylmethoxy)calix[4]arene-26,28-diol 在 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以84%的产率得到5-[3-(3-aminopropionylamino)phenyl]-17-(3-nitrophenyl)-25,27-bis(methoxycarbonylmethoxy)calix[4]arene-26,28-diol
  参考文献：
  名称：

  Host−[2]Rotaxane:  Advantage of Converging Functional Groups for Guest Recognition

  摘要：

  A host-[2]rotaxane was constructed by converting a diaminophenylcalix[4]arene into a [2]rotaxane using the DCC-rotaxane method (Zehnder, D.; Smithrud, D. B. Org. Lett. 2001, 16, 2485-2486). N-Ac-Arg groups were attached to the dibenzo-24-crown-8 ring of the rotaxane to provide a convergent functional group. To demonstrate the advantage provided by the rotaxane architecture for recognition of guests that contain a variety of functional groups, association constants (K-A) for N-Ac-Trp, indole, N-Ac-Gly, fluorescein, 1-(dimethylamino)-5-naphthalenesulfonate, and pyrene bound to the [2]rotaxane were determined by performing H-1 NMR and fluorescence spectroscopic experiments. The host-[2]rotaxane had the highest affinity for fluorescein with a K-A = 4.6 x 106 M-1 in a 98/2 buffer (1 mM phosphate, pH 7)/DMSO solution. A comparison of K-A values demonstrates that both the aromatic pocket and ring of the host-[2]rotaxane contribute binding free energy for complexation. Association constants were also derived for the same guests bound to the diaminophenylcalix[4]arene and to a diphenylcalix[4]arene that contained arginine residues displayed in a nonconvergent fashion. The host-[2]rotaxane provides higher affinity and specificity for most guests than the host with divergent N-Ac-Arg groups of the one that only has an aromatic pocket. For example, the K-A for the complex of the host-[2]rotaxane and fluorescein in the DMSO/water mixture is more than 2 orders of magnitude greater than association constants derived for the other hosts.

  DOI：

  10.1021/jo026522+
• 作为产物：
  描述：

  5,17-bis(3-nitrophenyl)-25,27-bis(hydroxycarbonylmethoxy)calix[4]arene-26,28-diol 在 palladium on activated charcoal 硫酸 、 氢气 、 N,N'-羰基二咪唑 作用下， 以 甲醇 、 氯仿 、 溶剂黄146 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 38.0h， 生成 5-[3-(3-tert-butoxycarbonylaminopropionylamino)phenyl]-17-(3-nitrophenyl)-25,27-bis(methoxycarbonylmethoxy)calix[4]arene-26,28-diol
  参考文献：
  名称：

  Host−[2]Rotaxane:  Advantage of Converging Functional Groups for Guest Recognition

  摘要：

  A host-[2]rotaxane was constructed by converting a diaminophenylcalix[4]arene into a [2]rotaxane using the DCC-rotaxane method (Zehnder, D.; Smithrud, D. B. Org. Lett. 2001, 16, 2485-2486). N-Ac-Arg groups were attached to the dibenzo-24-crown-8 ring of the rotaxane to provide a convergent functional group. To demonstrate the advantage provided by the rotaxane architecture for recognition of guests that contain a variety of functional groups, association constants (K-A) for N-Ac-Trp, indole, N-Ac-Gly, fluorescein, 1-(dimethylamino)-5-naphthalenesulfonate, and pyrene bound to the [2]rotaxane were determined by performing H-1 NMR and fluorescence spectroscopic experiments. The host-[2]rotaxane had the highest affinity for fluorescein with a K-A = 4.6 x 106 M-1 in a 98/2 buffer (1 mM phosphate, pH 7)/DMSO solution. A comparison of K-A values demonstrates that both the aromatic pocket and ring of the host-[2]rotaxane contribute binding free energy for complexation. Association constants were also derived for the same guests bound to the diaminophenylcalix[4]arene and to a diphenylcalix[4]arene that contained arginine residues displayed in a nonconvergent fashion. The host-[2]rotaxane provides higher affinity and specificity for most guests than the host with divergent N-Ac-Arg groups of the one that only has an aromatic pocket. For example, the K-A for the complex of the host-[2]rotaxane and fluorescein in the DMSO/water mixture is more than 2 orders of magnitude greater than association constants derived for the other hosts.

  DOI：

  10.1021/jo026522+

文献信息

• Host−[2]Rotaxane:  Advantage of Converging Functional Groups for Guest Recognition
  作者：Inese Smukste、Brian E. House、David B. Smithrud

  DOI：10.1021/jo026522+

  日期：2003.4.1

  A host-[2]rotaxane was constructed by converting a diaminophenylcalix[4]arene into a [2]rotaxane using the DCC-rotaxane method (Zehnder, D.; Smithrud, D. B. Org. Lett. 2001, 16, 2485-2486). N-Ac-Arg groups were attached to the dibenzo-24-crown-8 ring of the rotaxane to provide a convergent functional group. To demonstrate the advantage provided by the rotaxane architecture for recognition of guests that contain a variety of functional groups, association constants (K-A) for N-Ac-Trp, indole, N-Ac-Gly, fluorescein, 1-(dimethylamino)-5-naphthalenesulfonate, and pyrene bound to the [2]rotaxane were determined by performing H-1 NMR and fluorescence spectroscopic experiments. The host-[2]rotaxane had the highest affinity for fluorescein with a K-A = 4.6 x 106 M-1 in a 98/2 buffer (1 mM phosphate, pH 7)/DMSO solution. A comparison of K-A values demonstrates that both the aromatic pocket and ring of the host-[2]rotaxane contribute binding free energy for complexation. Association constants were also derived for the same guests bound to the diaminophenylcalix[4]arene and to a diphenylcalix[4]arene that contained arginine residues displayed in a nonconvergent fashion. The host-[2]rotaxane provides higher affinity and specificity for most guests than the host with divergent N-Ac-Arg groups of the one that only has an aromatic pocket. For example, the K-A for the complex of the host-[2]rotaxane and fluorescein in the DMSO/water mixture is more than 2 orders of magnitude greater than association constants derived for the other hosts.