4,6-二(4-羧苯基)嘧啶 | 609356-00-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 4,6-二(4-羧苯基)嘧啶
• 英文名称: 4,6-bis(4-carboxyphenyl)pyrimidine
• 英文别名: 4,6-di(4′-carboxyphenyl)pyrimidine；4,6-bis(4′-carboxyphenyl)pyrimidine；4,6-DI(4-Carboxyphenyl)pyrimidine；4-[6-(4-carboxyphenyl)pyrimidin-4-yl]benzoic acid
• CAS: 609356-00-5
• 化学式: C₁₈H₁₂N₂O₄
• 分子量: 320.304
• InChiKey: VWTUTWRNJIMOBH-UHFFFAOYSA-N

物化性质

• 沸点：
  606.2±55.0 °C(Predicted)
• 密度：
  1.383±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  N,N-二乙基乙二胺 、 4,6-二(4-羧苯基)嘧啶 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 4,6-Bis(4[(2-(diethylamino)ethyl)carboxamido]phenyl)pyrimidine
  参考文献：
  名称：

  Biarylpyrimidines: a new class of ligand for high-order DNA recognitionElectronic supplementary information (ESI) available: experimental details of UV melting studies and example spectroscopic and analytical data. See http://www.rsc.org/suppdata/cc/b3/b301554h/

  摘要：

  具有ω-氨基烷基取代基的联苯嘧啶类化合物已被设计为高阶DNA结构的配体：分光光度法、热学法及竞争平衡透析法检测显示，将取代基连接的功能基团由硫醚改为酰胺，可使其结构结合偏好从三链DNA转变为四链DNA；新型的配体无毒且对人类端粒酶具有中等抑制作用。

  DOI：

  10.1039/b301554h
• 作为产物：
  描述：

  4,6-bis(4-methoxycarbonylphenyl)pyrimidine 在 sodium hydroxide 作用下， 以100%的产率得到4,6-二(4-羧苯基)嘧啶
  参考文献：
  名称：

  Biarylpyrimidines: a new class of ligand for high-order DNA recognitionElectronic supplementary information (ESI) available: experimental details of UV melting studies and example spectroscopic and analytical data. See http://www.rsc.org/suppdata/cc/b3/b301554h/

  摘要：

  具有ω-氨基烷基取代基的联苯嘧啶类化合物已被设计为高阶DNA结构的配体：分光光度法、热学法及竞争平衡透析法检测显示，将取代基连接的功能基团由硫醚改为酰胺，可使其结构结合偏好从三链DNA转变为四链DNA；新型的配体无毒且对人类端粒酶具有中等抑制作用。

  DOI：

  10.1039/b301554h

文献信息

• Biarylpyrimidines: a new class of ligand for high-order DNA recognitionElectronic supplementary information (ESI) available: experimental details of UV melting studies and example spectroscopic and analytical data. See http://www.rsc.org/suppdata/cc/b3/b301554h/
  作者：Peter M. Murphy、Victoria A. Phillips、Sharon A. Jennings、Nichola C. Garbett、Jonathan B. Chaires、Terence C. Jenkins、Richard T. Wheelhouse

  DOI：10.1039/b301554h

  日期：2003.4.30

  Biarylpyrimidines bearing ω-aminoalkyl substituents have been designed as ligands for high-order DNA structures: spectrophotometric, thermal and competition equilibrium dialysis assays showed that changing the functional group for substituent attachment from thioether to amide switches the structural binding preference from triplex to tetraplex DNA; the novel ligands are non-toxic and moderate inhibitors of human telomerase.

  具有ω-氨基烷基取代基的联苯嘧啶类化合物已被设计为高阶DNA结构的配体：分光光度法、热学法及竞争平衡透析法检测显示，将取代基连接的功能基团由硫醚改为酰胺，可使其结构结合偏好从三链DNA转变为四链DNA；新型的配体无毒且对人类端粒酶具有中等抑制作用。
• Lanthanide–Organic Frameworks with Uncoordinated Lewis Base Sites: Tunable Luminescence, Antibiotic Detection, and Anticounterfeiting
  作者：Zhen-Hua Guo、Peng-Feng Zhang、Lu-Lu Ma、Yu-Xin Deng、Guo-Ping Yang、Yao-Yu Wang

  DOI：10.1021/acs.inorgchem.2c00224

  日期：2022.4.25

  new isostructural lanthanide metal–organic frameworks (Ln-MOFs), [Ln2(L)3DMA4]·2DMA}n (1-Ln, where Ln = Eu, Tb, or EuxTb1–x), were first constructed via the solvothermal reactions of 4,6-di(4-carboxyphenyl)pyrimidine and Ln3+ ions. 1-Ln exhibits a 4-connected two-dimensional framework endowed with uncoordinated Lewis base sites. An exploration of luminescence sensing demonstrated 1-Eu can be used for

  几种新的同构镧系金属有机骨架 (Ln-MOFs)，[Ln 2 (L) 3 DMA 4 ]·2DMA} n ( 1-Ln , 其中 Ln = Eu, Tb, or Eu x Tb 1– x ),最初是通过4,6-二(4-羧基苯基)嘧啶和Ln 3+离子的溶剂热反应构建的。1-Ln展示了一个 4 连接的二维框架，具有不协调的路易斯碱基。对发光传感的探索证明了1-Eu可用于选择性检测其他抗生素、血浆和尿液中的二甲硝唑和甲硝唑类抗生素，是一种特殊的可回收发光探针。更重要的是， 1-Ln的发光油墨是不可见的、颜色可调的、稳定的，这将大大提高其防伪应用。
• Highly Efficient I₂ Sorption, CO₂ Capture, and Catalytic Conversion by Introducing Nitrogen Donor Sites in a Microporous Co(II)-Based Metal–Organic Framework
  作者：Zhen-Hua Guo、Yin-Di Zhang、Qian-Qian Wang、Yao Wang、Peng-Feng Zhang、Wen-Yan Zhang、Guo-Ping Yang、Yao-Yu Wang

  DOI：10.1021/acs.inorgchem.2c00383

  日期：2022.5.9

  6-bis(4′-carboxyphenyl)pyrimidine (H2L) linker. Interestingly, 1 exhibits exceptional properties for I2 sorption, CO2 capture, and catalytic conversion. Particularly, I2 can be efficiently removed in both vapor and solution forms, and the adsorption amount can reach 676.25 and 345.28 mg g–1, respectively. Furthermore, complex 1 displays high adsorption capacity for CO2 (53.78 cm3 g–1, 273 K). Consequently

  最近，由于严重的全球气候变化和核能带来的环境问题，用于高效捕获CO 2和I 2的多孔吸收剂的开发引起了相当大的关注。因此，通过使用异官能团合理构建了具有非配位N原子的独特多孔金属有机骨架（MOF），[Co(L)]·DMF·2H 2 O} n ( 1 , DMF = N , N-二甲基甲酰胺) 4,6-双（4'-羧基苯基）嘧啶（H 2 L）接头。有趣的是，1表现出对 I 2吸附、CO 2的特殊性能捕获和催化转化。特别是，I 2可以以蒸气和溶液形式有效去除，吸附量分别可以达到676.25和345.28 mg g -1。此外，配合物1对 CO 2具有高吸附能力（53.78 cm 3 g –1 , 273 K）。因此，由于其优异的吸附性能， 1有望成为一种有前途且实用的环境净化材料。
• Design, Synthesis, and Evaluation of Novel Biarylpyrimidines:  A New Class of Ligand for Unusual Nucleic Acid Structures
  作者：Richard T. Wheelhouse、Sharon A. Jennings、Victoria A. Phillips、Dimitrios Pletsas、Peter M. Murphy、Nichola C. Garbett、Jonathan B. Chaires、Terence C. Jenkins

  DOI：10.1021/jm060315a

  日期：2006.8.1

  Biarylpyrimidines are characterized as selective ligands for higher-order nucleic acid structures. A concise and efficient synthesis has been devised incorporating Suzuki biaryl cross-coupling of dihalopyrimidines. Two ligand series are described based on the parent thioether 4,6-bis[4-[[2-(dimethylamino)ethyl]mercapto]phenyl] pyrimidine (1a) and amide 4,6-bis(4[(2-(dimethylamino) ethyl) carboxamido] phenyl) pyrimidine (2a) compounds. In UV thermal denaturation studies with the poly(dA),[poly(dT)](2) triplex structure, thioethers showed stabilization of the triplex form (Delta T-m <= 20 degrees C). In contrast, amides showed duplex stabilization (Delta T-m <= 15 degrees C) and either negligible stabilization or specific destabilization (Delta T-m = 5 degrees C) of the triplex structure. Full spectra of nucleic acid binding preferences were determined by competition dialysis. The strongest interacting thioether bound preferentially to the poly(dA)(.)[poly(dT)](2) triplex, Kapp) 1.6 x 10(5) M-1 (40 x Kapp for CT DNA duplex). In contrast, the strongest binding amide selected the (T(2)G(20)T(2)) 4 quadruplex structure, Kapp) 0.31 x 10(5) M-1 (6.5 x K-app for CT DNA duplex).