5-(4-formylphenyl)pyridine-2-carbonitrile | 869767-74-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-(4-formylphenyl)pyridine-2-carbonitrile
• CAS: 869767-74-8
• 化学式: C₁₃H₈N₂O
• 分子量: 208.219
• InChiKey: AYTPKYBBGFTVKL-UHFFFAOYSA-N

物化性质

• 熔点：
  193-194 °C
• 沸点：
  429.6±40.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 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：
  53.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-formylphenyl)pyridine-2-carbonitrile 在 盐酸羟胺 、 potassium tert-butylate 、 对苯醌 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 生成 2-{4-[6-(N-hydroxyamidino)pyridin-3pyl]phenyl}-1H-benzimidazole-5-N-hydroxyamidine
  参考文献：
  名称：

  Dicationic near-linear biphenyl benzimidazole derivatives as DNA-targeted antiprotozoal agents

  摘要：

  A series of near-linear biphenyl benzimidazole diamidines 5a-h were synthesized from their respective diamidoximes (4a-h), through the bis-O-acetoxyamidoxime, followed by hydrogenation in glacial acetic acid/ethanol in the presence of Pd-C. Compounds 4a-h were obtained in three steps, starting with the Suzuki coupling reaction of the appropriate haloarylcarbonitriles la-g or 4-bromo-2-fluorobenzaldehyde with 4-formylphenylboronic acid or 4-cyanophenylboronic acid to form the anticipated 4-formylbiphenyl carbonitrile analogues 2a-h. Subsequent condensation of the formyl derivatives 2a-h with 3,4-diaminobenzonitrile in the presence of sodium bisulfite or 1,4-benzoquinone gave the desired dinitriles 3a-h, the precursors for 4a-h. All the diamidines showed strong DNA affinities, as judged by high Delta T-m values with poly(dA.dT)(2). The compounds were quite active in vitro versus Trypanosoma brucei rhodesiense, giving IC50 values ranging from 3 to 37 nM. These compounds were even more active versus Plasmodium falciparum, exhibiting IC50 values ranging from 0.5 to 23 nM. The compounds showed moderate to good activity in vivo in the STIB900 model for acute African trypanosomiasis. The most active compounds 5b and e gave 3/4 cures on an IP dosage of 20 mg/kg. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.024
• 作为产物：
  描述：

  4-甲酰基苯硼酸 、 5-溴-2-氰基吡啶 在 四(三苯基膦)钯 碳酸氢钠 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 12.0h， 以64%的产率得到5-(4-formylphenyl)pyridine-2-carbonitrile
  参考文献：
  名称：

  Dicationic near-linear biphenyl benzimidazole derivatives as DNA-targeted antiprotozoal agents

  摘要：

  A series of near-linear biphenyl benzimidazole diamidines 5a-h were synthesized from their respective diamidoximes (4a-h), through the bis-O-acetoxyamidoxime, followed by hydrogenation in glacial acetic acid/ethanol in the presence of Pd-C. Compounds 4a-h were obtained in three steps, starting with the Suzuki coupling reaction of the appropriate haloarylcarbonitriles la-g or 4-bromo-2-fluorobenzaldehyde with 4-formylphenylboronic acid or 4-cyanophenylboronic acid to form the anticipated 4-formylbiphenyl carbonitrile analogues 2a-h. Subsequent condensation of the formyl derivatives 2a-h with 3,4-diaminobenzonitrile in the presence of sodium bisulfite or 1,4-benzoquinone gave the desired dinitriles 3a-h, the precursors for 4a-h. All the diamidines showed strong DNA affinities, as judged by high Delta T-m values with poly(dA.dT)(2). The compounds were quite active in vitro versus Trypanosoma brucei rhodesiense, giving IC50 values ranging from 3 to 37 nM. These compounds were even more active versus Plasmodium falciparum, exhibiting IC50 values ranging from 0.5 to 23 nM. The compounds showed moderate to good activity in vivo in the STIB900 model for acute African trypanosomiasis. The most active compounds 5b and e gave 3/4 cures on an IP dosage of 20 mg/kg. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.024

文献信息

• NOVEL LIQUID CRYSTAL COMPOUND AND USE THEREOF
  申请人：LG Chem, Ltd.

  公开号：US20190016956A1

  公开（公告）日：2019-01-17

  The present application relates to a novel liquid crystal compound and a use thereof. The novel liquid crystal compounds of the present application can exhibit a smectic A phase over a wide temperature range. The novel liquid crystal compounds of the present application can be usefully used in the technical fields to which smectic A liquid crystals can be applied, for example, bistable devices.

  这个申请涉及一种新型液晶化合物及其用途。本申请的新型液晶化合物可以在广泛的温度范围内表现出一种列状A相。本申请的新型液晶化合物可以在列状A液晶可应用的技术领域中有用地使用，例如，双稳态器件。
• Liquid crystal compound and use thereof
  申请人：LG Chem, Ltd.

  公开号：US10954444B2

  公开（公告）日：2021-03-23

  The present application relates to a novel liquid crystal compound and a use thereof. The novel liquid crystal compounds of the present application can exhibit a smectic A phase over a wide temperature range. The novel liquid crystal compounds of the present application can be usefully used in the technical fields to which smectic A liquid crystals can be applied, for example, bistable devices.

  本申请涉及一种新型液晶化合物及其用途。本申请的新型液晶化合物可以在很宽的温度范围内呈现出共晶 A 相。本申请的新型液晶化合物可有效地应用于可应用 Smectic A 液晶的技术领域，例如双稳态器件。