4,6-bis(4-fluorophenyl)pyrimidine | 168915-00-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4,6-bis(4-fluorophenyl)pyrimidine
• CAS: 168915-00-2
• 化学式: C₁₆H₁₀F₂N₂
• 分子量: 268.266
• InChiKey: QHXSHRCALYKRKU-UHFFFAOYSA-N

物化性质

• 熔点：
  102.6-103.6 °C(Solv: methanol (67-56-1); water (7732-18-5))
• 沸点：
  405.6±35.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-甲基-2-丙硫醇钠盐 、 4,6-bis(4-fluorophenyl)pyrimidine 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以64%的产率得到4,6-bis(4-tert-butylmercaptophenyl)pyrimidine
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Novel Biarylpyrimidines:  A New Class of Ligand for Unusual Nucleic Acid Structures

  摘要：

  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).

  DOI：

  10.1021/jm060315a
• 作为产物：
  描述：

  对溴氟苯 在 四(三苯基膦)钯 sodium carbonate 、 magnesium 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 4,6-bis(4-fluorophenyl)pyrimidine
  参考文献：
  名称：

  通过4,6-二氯嘧啶的铃木和熊田偶联反应合成4,6-二取代的嘧啶

  摘要：

  通过Suzuki和4,6-二氯嘧啶的Kumada偶联反应合成了一系列4,6-二取代的嘧啶。

  DOI：

  10.1016/s0022-1139(02)00279-8

文献信息

• N-Heterocyclic Carbene-Tricyclohexylphosphine Palladium(II) Complex: Synthesis, Crystal Structure and Application in Suzuki Reaction of Aryl Chlorides
  作者：Chen Xu、Xin-Qi Hao、Zhen Li、Lu-Meng Duan、Zhi-Qiang Wang、Bao-Ming Ji、Mao-Ping Song

  DOI：10.5012/bkcs.2012.33.10.3430

  日期：2012.10.20
• Ruthenium-Catalyzed Direct ortho-Alkynylation of Arenes with Chelation Assistance
  作者：Mamoru Tobisu、Naoto Chatani、Yusuke Ano

  DOI：10.1055/s-0032-1316556

  日期：——

  The ruthenium-catalyzed direct alkynylation of arenes with the chelation assistance of nitrogen-containing heterocycles including pyridine, pyrimidine, pyrazole, and imidazole are described. The alkynylation is successful even in the presence of an acidic N-H bond. Broad compatibility with functional groups is observed under catalytic conditions. The obtained alkynylated products could serve as precursors for polycyclic heteroarenes.
• Two-Photon Spectroscopy as a New Sensitive Method for Determining the DNA Binding Mode of Fluorescent Nuclear Dyes
  作者：Phi H. Doan、Demar R. G. Pitter、Andrea Kocher、James N. Wilson、Theodore Goodson

  DOI：10.1021/jacs.5b02674

  日期：2015.7.29

  A new optical strategy to determine the binding modes (intercalation vs groove binding) of small fluorescent organic molecules with calf thymus DNA was developed using two-photon absorption (TPA) spectroscopy. Two-photon excited emission was utilized to investigate a series of fluorescent nuclear dyes. The results show that TPA cross-sections are able to differentiate the fine details between the DNA binding modes. Groove binding molecules exhibit an enhanced TPA cross-section due to the DNA electric field induced enhancement of the transition dipole moment, while intercalative binding molecules exhibit a decrease in the TPA cross-section. Remarkably, the TPA cross-section of 4,6-bis(4-(4-methylpiperazin-1-yl)phenyl) pyrimidine is significantly enhanced (13.6-fold) upon binding with DNA. The sensitivity of our TPA methodology is compared to circular dichroism spectroscopy. TPA demonstrates superior sensitivity by more than an order of magnitude at low DNA concentrations. This methodology can be utilized to probe DNA interactions with other external molecules such as proteins, enzymes, and drugs.
• Synthesis of 4,6-disubstituted pyrimidines via Suzuki and Kumada coupling reaction of 4,6-dichloropyrimidine
  作者：Feng-ling Qing、Ruowen Wang、Benhan Li、Xing Zheng、Wei-Dong Meng

  DOI：10.1016/s0022-1139(02)00279-8

  日期：2003.3

  A series of 4,6-disubstituted pyrimidines were synthesized via Suzuki and Kumada coupling reaction of 4,6-dichloropyrimidine.

  通过Suzuki和4,6-二氯嘧啶的Kumada偶联反应合成了一系列4,6-二取代的嘧啶。
• 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).