5-nitro-2-(thiophen-3-yl)benzoic acid | 919087-94-8

• 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-nitro-2-(thiophen-3-yl)benzoic acid
• 英文别名: 5-Nitro-2-(thiophen-3-yl)benzoic acid；5-nitro-2-thiophen-3-ylbenzoic acid
• CAS: 919087-94-8
• 化学式: C₁₁H₇NO₄S
• 分子量: 249.247
• InChiKey: HLRYSHFDQIZNAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲醇 、 europium(III) chloride hexahydrate 、 5-nitro-2-(thiophen-3-yl)benzoic acid 以 甲醇 为溶剂， 生成 Eu2(5-nitro-2-thiophen-3-yl-benzoato)6(methanol)6
  参考文献：
  名称：

  Eu(III) and Tb(III) Luminescence Sensitized by Thiophenyl-Derivatized Nitrobenzoato Antennas

  摘要：

  Thiophenyl-derivatized nitrobenzoic acid ligands have been evaluated as possible sensitizers of Eu(III) and Tb(III) luminescence. The resulting solution and solid- state species were isolated and characterized by luminescence spectroscopy and X-ray crystallography. The Eu(III) complex with 2-nitro-3-thiophen-3-yl-benzoic acid, 1, crystallizes in the monoclinic space group C2/c with a = 28.569(3) angstrom, b = 17.7726(18) angstrom, c = 17.7073(18) angstrom, beta = 126.849(2)degrees, and V = 7194.6(13) angstrom(3). The Tb(III) complex with this ligand, 2, is isostructural, and its cell parameters are a = 29.755(6) angstrom, b = 18.123(4) angstrom, c = 19.519(4) angstrom, beta = 130.35(3)degrees, and V = 8021(3) angstrom(3). Eu(III) crystallizes with. 3-nitro-2-thiophen-3-yl-benzoic acid as a triclinic complex, 3, in the space group P (1) over barh with a = 11.045(2) angstrom, b = 12.547(3) angstrom, c = 15.500(3) angstrom, alpha = 109.06(3)degrees, beta = 94.79(3)degrees, gamma = 107.72(3)degrees. and V = 1893.5(7) angstrom(3). With the ligand 5-nitro-2-thiophen-3-yl-benzoic acid, Eu(III) yields another molecular compound, 4, triclinic P (1) over barh, with a = 10.649(2) angstrom, b = 14.009(3) angstrom, c = 15.205(3) angstrom, alpha = 112.15(3)degrees, beta = 100.25(3)degrees, gamma = 106.96(3)degrees, and V = 1900.5(7) angstrom(3). All compounds dissolve in water and methanol, and the methanolic solutions are luminescent. The solution species have a metal ion-to-ligand ratio of 1:1. The quantum yields have been determined to be in the range of 0.9-3.1% for Eu(III) and 4.7-9.8% for Tb(III). The highest values of these correspond to the most intense luminescence reported for Ln(III) solutions with this type of sensitizer. The lifetimes of luminescence are in the range of 248.3-338.9 mu s for Eu(III) and 208.6-724.9 mu s for Tb(III). The stability constants are in the range of log beta(11) = 2.73-4.30 for Eu(III) and 3.34-4.18 for Tb(III) and, along with the energy migration pathways, are responsible for the reported efficiency of sensitization.

  DOI：

  10.1021/ic061272r
• 作为产物：
  描述：

  3-噻吩硼酸 、 2-溴-5-硝基苯甲酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 以25%的产率得到5-nitro-2-(thiophen-3-yl)benzoic acid
  参考文献：
  名称：

  靶向 MEP 途径中的 IspD 酶：新型片段类的鉴定

  摘要：

  针对Pf IspD 酶对巴斯夫文库的一部分进行筛选，结果发现吡咯是一种尚未开发的化学支架，能够靶向 MEP 途径中的第三种酶。围绕片段命中化合物进行的详细构效关系 (SAR) 研究帮助我们成功提高了效力和理化性质。

  DOI：

  10.1002/cmdc.202100679

文献信息

• Targeting the IspD Enzyme in the MEP Pathway: Identification of a Novel Fragment Class
  作者：Eleonora Diamanti、Mostafa M. Hamed、Antoine Lacour、Patricia Bravo、Boris Illarionov、Markus Fischer、Matthias Rottmann、Matthias Witschel、Anna K. H. Hirsch

  DOI：10.1002/cmdc.202100679

  日期：2022.3.4

  Screening of a part of the BASF library against the PfIspD enzyme led to the identification of a pyrrole as an underexplored chemical scaffold that is able to target the third enzyme in the MEP pathway. A detailed structure–activity relationship (SAR) study around the fragment hit compound helped us to successfully improve the potency as well as the physicochemical properties.

  针对Pf IspD 酶对巴斯夫文库的一部分进行筛选，结果发现吡咯是一种尚未开发的化学支架，能够靶向 MEP 途径中的第三种酶。围绕片段命中化合物进行的详细构效关系 (SAR) 研究帮助我们成功提高了效力和理化性质。
• Eu(III) and Tb(III) Luminescence Sensitized by Thiophenyl-Derivatized Nitrobenzoato Antennas
  作者：Subha Viswanathan、Ana de Bettencourt-Dias

  DOI：10.1021/ic061272r

  日期：2006.12.1

  Thiophenyl-derivatized nitrobenzoic acid ligands have been evaluated as possible sensitizers of Eu(III) and Tb(III) luminescence. The resulting solution and solid- state species were isolated and characterized by luminescence spectroscopy and X-ray crystallography. The Eu(III) complex with 2-nitro-3-thiophen-3-yl-benzoic acid, 1, crystallizes in the monoclinic space group C2/c with a = 28.569(3) angstrom, b = 17.7726(18) angstrom, c = 17.7073(18) angstrom, beta = 126.849(2)degrees, and V = 7194.6(13) angstrom(3). The Tb(III) complex with this ligand, 2, is isostructural, and its cell parameters are a = 29.755(6) angstrom, b = 18.123(4) angstrom, c = 19.519(4) angstrom, beta = 130.35(3)degrees, and V = 8021(3) angstrom(3). Eu(III) crystallizes with. 3-nitro-2-thiophen-3-yl-benzoic acid as a triclinic complex, 3, in the space group P (1) over barh with a = 11.045(2) angstrom, b = 12.547(3) angstrom, c = 15.500(3) angstrom, alpha = 109.06(3)degrees, beta = 94.79(3)degrees, gamma = 107.72(3)degrees. and V = 1893.5(7) angstrom(3). With the ligand 5-nitro-2-thiophen-3-yl-benzoic acid, Eu(III) yields another molecular compound, 4, triclinic P (1) over barh, with a = 10.649(2) angstrom, b = 14.009(3) angstrom, c = 15.205(3) angstrom, alpha = 112.15(3)degrees, beta = 100.25(3)degrees, gamma = 106.96(3)degrees, and V = 1900.5(7) angstrom(3). All compounds dissolve in water and methanol, and the methanolic solutions are luminescent. The solution species have a metal ion-to-ligand ratio of 1:1. The quantum yields have been determined to be in the range of 0.9-3.1% for Eu(III) and 4.7-9.8% for Tb(III). The highest values of these correspond to the most intense luminescence reported for Ln(III) solutions with this type of sensitizer. The lifetimes of luminescence are in the range of 248.3-338.9 mu s for Eu(III) and 208.6-724.9 mu s for Tb(III). The stability constants are in the range of log beta(11) = 2.73-4.30 for Eu(III) and 3.34-4.18 for Tb(III) and, along with the energy migration pathways, are responsible for the reported efficiency of sensitization.