(E)-N-(2-(1,4,7,10,13-Pentaoxa-16-azacyclooctadecan-16-yl)ethyl)-2-(3-hydroxy-4-(4-methoxyphenyl)-5-oxofuran-2(5H)-ylidene)-2-(4-methoxyphenyl)acetamide | 1415681-27-4

• 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: (E)-N-(2-(1,4,7,10,13-Pentaoxa-16-azacyclooctadecan-16-yl)ethyl)-2-(3-hydroxy-4-(4-methoxyphenyl)-5-oxofuran-2(5H)-ylidene)-2-(4-methoxyphenyl)acetamide
• 英文别名: (2E)-N-(1,4,7,10,13,16-hexaoxacyclooctadec-2-ylmethyl)-2-[3-hydroxy-4-(4-methoxyphenyl)-5-oxofuran-2-ylidene]-2-(4-methoxyphenyl)acetamide
• CAS: 1415681-27-4
• 化学式: C₃₃H₄₁NO₁₂
• 分子量: 643.688
• InChiKey: VOMOJSFXIVKJJE-OWWNRXNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  46
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  150
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  对甲氧基苯乙腈 在 sodium 作用下， 以 乙醇 、 二氯二氟甲烷 为溶剂， 反应 2.5h， 生成 (E)-N-(2-(1,4,7,10,13-Pentaoxa-16-azacyclooctadecan-16-yl)ethyl)-2-(3-hydroxy-4-(4-methoxyphenyl)-5-oxofuran-2(5H)-ylidene)-2-(4-methoxyphenyl)acetamide
  参考文献：
  名称：

  A new series of Cs+, K+ and Na+ chelators: Synthesis, kinetics, thermodynamics and modeling

  摘要：

  The synthesis of two molecules, B1 and B2, based on elements of norbadione A, the natural Cs+ chelator in mushrooms, associated, in the case of B2, with an 18-crown-6 ether is reported. Thermodynamic and kinetic analyses performed in water, ethanol and ethanol/water 9/1 v/v (M1) show in M1 and ethanol that B1 and B2 form stable complexes with Na+, K+ and Cs+. Affinity constants, measured spectrophotometrically in ethanol and M1, by the use of the SPECFIT program, are in the 10(5) and 10(6) range for B1 and B2, respectively. The second-order rate constants are in the 10(6)-10(7) M-1 s(-1) range and the first-order rate constants about unity. The ratios of the second-order/first-order rate constants confirm the thermodynamic results in EtOH. The kinetic processes become much too fast to allow runs in M1. Molecular simulations in EtOH imply the existence of two isomers for each of the Cs+/B1 and Cs+/B2 complexes. With B1, the more stable one is that in which the two enolates are parallel and mimic the alkali-metal inclusion cavity already envisaged for norbadione A. With B2, two similar structures are extracted, in both of which Cs+ is included in the crown ether and capped by the enolate. The affinity of B1 for Cs+ is comparable to that of norbadione A, whereas that of B2 is higher. These results are encouraging as they introduce a new series of alkali chelators which can lead to molecules capable of complexing Cs-137(+) for radioactive decontamination. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.08.009

文献信息

• A new series of Cs+, K+ and Na+ chelators: Synthesis, kinetics, thermodynamics and modeling
  作者：Alexandre Korovitch、Antoine Le Roux、Florent Barbault、Miryana Hémadi、Nguyêt-Thanh Ha-Duong、Claude Lion、Alain Wagner、Jean-Michel El Hage Chahine

  DOI：10.1016/j.ica.2012.08.009

  日期：2013.1

  The synthesis of two molecules, B1 and B2, based on elements of norbadione A, the natural Cs+ chelator in mushrooms, associated, in the case of B2, with an 18-crown-6 ether is reported. Thermodynamic and kinetic analyses performed in water, ethanol and ethanol/water 9/1 v/v (M1) show in M1 and ethanol that B1 and B2 form stable complexes with Na+, K+ and Cs+. Affinity constants, measured spectrophotometrically in ethanol and M1, by the use of the SPECFIT program, are in the 10(5) and 10(6) range for B1 and B2, respectively. The second-order rate constants are in the 10(6)-10(7) M-1 s(-1) range and the first-order rate constants about unity. The ratios of the second-order/first-order rate constants confirm the thermodynamic results in EtOH. The kinetic processes become much too fast to allow runs in M1. Molecular simulations in EtOH imply the existence of two isomers for each of the Cs+/B1 and Cs+/B2 complexes. With B1, the more stable one is that in which the two enolates are parallel and mimic the alkali-metal inclusion cavity already envisaged for norbadione A. With B2, two similar structures are extracted, in both of which Cs+ is included in the crown ether and capped by the enolate. The affinity of B1 for Cs+ is comparable to that of norbadione A, whereas that of B2 is higher. These results are encouraging as they introduce a new series of alkali chelators which can lead to molecules capable of complexing Cs-137(+) for radioactive decontamination. (C) 2012 Elsevier B. V. All rights reserved.