C4A-Phe-OMe | 852944-02-6

• 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: C4A-Phe-OMe
• 英文别名: methyl (2S)-3-phenyl-2-[[2-[[5,11,17,23-tetratert-butyl-26,28-dihydroxy-27-[2-[[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-2-oxoethoxy]-25-pentacyclo[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-dodecaenyl]oxy]acetyl]amino]propanoate
• CAS: 852944-02-6
• 化学式: C₆₈H₈₂N₂O₁₀
• 分子量: 1087.41
• InChiKey: UWYPXLGMNFHRBQ-ATMVKLMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.1
• 重原子数：
  80
• 可旋转键数：
  20
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  170
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  C4A-Phe-OMe 在 一水合肼 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 24.0h， 以79%的产率得到2,2'-((15,35,55,75-tetra-tert-butyl-32,72-dihydroxy-1,3,5,7(1,3)-tetrabenzenacyclooctaphane-12,52-diyl)bis(oxy))bis(N-((S)-1-hydrazineyl-1-oxo-3-phenylpropan-2-yl)acetamide)
  参考文献：
  名称：

  基于带有两个丹磺酰基的杯[4]芳烃的氨基酸阴离子荧光传感器

  摘要：

  合成了两种含有酰肼和丹磺酰基的新型手性杯[4]芳烃，并通过CHCl 3中的荧光和1 H NMR光谱检查了它们的对映选择性识别能力。结果表明4a和4b对N-保护的丙氨酸或苯丙氨酸阴离子均具有优异的对映选择性。

  DOI：

  10.1016/j.tetasy.2005.02.032
• 作为产物：
  描述：

  L-苯丙氨酸甲酯盐酸盐 、 25,27-bis(methoxycarboxylic, acid)-26,28-dihydroxy-4-tert-butylcalix-[4]arene 在 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以56%的产率得到C4A-Phe-OMe
  参考文献：
  名称：

  Experimental and Computational Studies of Selective Recognition of Hg²⁺ by Amide Linked Lower Rim 1,3-Dibenzimidazole Derivative of Calix[4]arene: Species Characterization in Solution and that in the Isolated Complex, Including the Delineation of the Nanostructures

  摘要：

  Amide linked lower rim 1,3-dibenzimidazole derivative of calix[4]arene, L has been shown to be sensitive and selective to Hg2+ in aqueous acetonitrile solution based on fluorescence spectroscopy, and the stoichiometry of the complexed species has been found to be 1:1. The selectivity of L toward Hg2+ has been shown among 11 M2+ ions, viz., Mn2+, Fe2+, CO2+, Ni2+, Cu2+, Zn2+, Cd2+, Hg2+, Ph2+, Ca2+, and Mg2+ studied, including those of the mercury group and none of these ions impede the recognition of Hg2+ by L. Role of the solvent on the recognition of Hg2+ has been demonstrated. The role of calix[4]arene platform and the benzimidazole moieties in the recognition of Hg2+ by L has been delineated upon performing such studies with five different molecules of relevance as reference molecular systems. The binding cores formed by the receptor L and the reference compounds have been established based on the single crystal XRD structures, and the preferential metal ion binding cores have been discussed. The binding, of Hg2+ with L has been further established based on H-1 and C-13 NMR, ESI MS, absorption, and fluorescence lifetime measurements. Some of these techniques have been used to establish the stoichiometry of the species formed. The complex species formed between L and Hg2+ have been isolated and characterized and found to be 1:1 species even in the isolated complex. Whereas transmission electron microscopy (TEM), atomic force microscopy (AFM), and scanning electron microscopy (SEM) provided the nanostructural behavior of L, the TEM and SEM demonstrated that the mercury complex has different characteristics when compared to L. The TEM, SEM, and powder XRD studies revealed that whereas L is crystalline, that of the mercury complex is not, perhaps a reason for not being able to obtain single crystals of the complex. Binding characteristics of Hg2+ toward L have been established based on the DFT computational calculations.

  DOI：

  10.1021/jo800073g

文献信息

• 1,3-Diamido-calix[4]arene Conjugates of Amino Acids: Recognition of −COOH Side Chain Present in Amino Acids, Peptides, and Proteins by Experimental and Computational Studies
  作者：Amitabha Acharya、Balaji Ramanujam、Jugun Prakash Chinta、Chebrolu P. Rao

  DOI：10.1021/jo101759f

  日期：2011.1.7

  free −COOH moiety from the guest molecule. AFM, SEM, and DLS data exhibited spherical particles with a hundred-fold reduction in the size of the complexes when compared to the particles of the precursors. These spherical particles have been computationally modeled to possess hexameric species reminiscent of the hexameric micellar structures shown for a Ag+ complex of a calix[6]arene reported in the literature

  已经合成并表征了杯[4]芳烃的下边缘1，3-二叠氮共轭物，并通过单晶XRD确定了其中一些的结构。通过在水溶液中开启荧光，已显示具有末端-COOH部分的酰胺杯-杯偶联物显示出对具有-COOH部分的客体分子（即Asp，Glu以及还原和氧化的谷胱甘肽（GSH，GSSG））的识别与乙腈和甲醇溶液相比，通过形成1：1络合物与对照分子进行比较。形成的配合物已通过质谱显示，并且配合物的结构特征是基于DFT计算得出的。观察到的通过Phe-calix共轭物识别Asp / Glu的缔合常数，即532/676 M -1，比所报道的识别缬氨酸，亮氨酸，苯丙氨酸，His和Trp组成更高（16-63中号-1）通过水溶性杯芳烃（竞技场，G。等人。四面体通讯。1999，40， 1597）。为了这种识别，客体分子应该有一个游离的-COOH部分。与前驱体的颗粒相比，AFM，SEM和DLS数据显示出球形颗粒，其配合物尺寸减小了
• Calix[4]arene-Based Chromogenic Chemosensor for the α-Phenylglycine Anion: Synthesis and Chiral Recognition
  作者：Guang-Yan Qing、Yong-Bing He、Yang Zhao、Chen-Guang Hu、Shun-Ying Liu、Xi Yang

  DOI：10.1002/ejoc.200500704

  日期：2006.3

  recognition for the enantiomers of the α-phenylglycine anions (3a: Kass(L)/Kass(D) = 4.76; 3b: Kass(D)/Kass(L) = 2.84). The marked colour changes observed for the complexation of 3a with the chiral anions and the good enantioselective recognition reveal that receptor 3a could be used as a good chiral chromogenic chemosensor for the enantiomers of the α-phenylglycine anion. (© Wiley-VCH Verlag GmbH & Co. KGaA

  已经合成了基于杯[4]芳烃的双臂手性阴离子受体 3a 和 3b，并通过 UV/Vis 吸收和 1H NMR 光谱检查了它们的手性阴离子结合能力。非线性曲线拟合结果表明3a和3b通过多重氢键相互作用与L-或D-α-苯基甘氨酸阴离子形成1:1的化学计量配合物，并对α-苯基甘氨酸阴离子的对映异构体表现出良好的对映选择性识别（3a ：卡斯（L）/卡斯（D）= 4.76；3b：卡斯（D）/卡斯（L）= 2.84）。观察到 3a 与手性阴离子络合的显着颜色变化和良好的对映选择性识别表明，受体 3a 可用作 α-苯基甘氨酸阴离子对映异构体的良好手性显色化学传感器。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Sensitive fluorescent sensors for malate based on calix[4]arene bearing anthracene
  作者：Guang-yan Qing、Yong-bing He、Zhi-hong Chen、Xiao-jun Wu、Ling-zhi Meng

  DOI：10.1016/j.tetasy.2006.11.043

  日期：2006.11

  Two chiral fluorescence receptors 3a and 3b based on calix[4]arenes were synthesized, and their chiral recognition properties for enantiomeric malate were studied by fluorescence and 1H NMR spectra in CHCl3. The addition of either l- or d-malate caused obvious fluorescence quenching of the host solution. Different fluorescent responses demonstrate that the two receptors have good enantioselective recognition

  合成了两种基于杯[4]芳烃的手性荧光受体3a和3b，并在CHCl 3中通过荧光和1 H NMR谱研究了手性对苹果酸的手性识别性能。l-或d-苹果酸的加入导致宿主溶液明显的荧光猝灭。不同的荧光反应表明这两种受体对苹果酸具有良好的对映选择性识别能力。