6-(4-三氟甲基-苯基)-吡啶-2-羧酸 | 924817-68-5

• 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
• 中文名称: 6-(4-三氟甲基-苯基)-吡啶-2-羧酸
• 英文名称: 6-(4-trifluoromethylphenyl)pyridine-2-carboxylic acid
• 英文别名: 6-(4-trifluoromethylphenyl)-2-pyridinecarboxylic acid；6-(4-(trifluoromethyl)phenyl)picolinic acid；6-[4-(trifluoromethyl)phenyl]pyridine-2-carboxylic acid
• CAS: 924817-68-5
• 化学式: C₁₃H₈F₃NO₂
• 分子量: 267.207
• InChiKey: JBAJBPRCHPGONU-UHFFFAOYSA-N

物化性质

• 沸点：
  390.3±42.0 °C(Predicted)
• 密度：
  1.377±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 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,H320,H335

反应信息

• 作为反应物：
  描述：

  6-(4-三氟甲基-苯基)-吡啶-2-羧酸 在 氧气 、 potassium acetate 、 palladium diacetate 、 C₁₉H₂₄N₂O 、 对苯醌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 110.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以79%的产率得到3-hydroxy-6-(4-(trifluoromethyl)phenyl)picolinic acid
  参考文献：
  名称：

  互变异构配体能够与分子氧进行定向 C-H 羟基化

  摘要：

  当使用氧气作为氧化剂时，使用过渡金属催化剂对芳基碳氢键进行羟基化已被证明具有挑战性。在这里，我们报告了一种钯配合物，它带有双齿吡啶/吡啶酮配体，可在与羧酸相邻的环位置有效地催化该反应。红外、X 射线和计算分析支持从单阴离子 (L,X) 到中性 (L,L) 配位的配体互变异构在好氧碳氢羟基化反应的催化循环中的可能作用。由杂环决定的传统位点选择性被这种催化剂推翻，从而允许在以前无法接近的位点对药物感兴趣的化合物进行后期修饰。

  DOI：

  10.1126/science.abg2362
• 作为产物：
  描述：

  6-溴吡啶-2-羧酸乙酯 在 四(三苯基膦)钯 、 水 、 sodium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 生成 6-(4-三氟甲基-苯基)-吡啶-2-羧酸
  参考文献：
  名称：

  New class of NCS-free cyclometalated ruthenium(II) complexes with 6-phenylpyridine-2-carboxylate for use as near-infrared sensitizers in dye-sensitized solar cells

  摘要：

  Three examples, FT102, FT90, and FT117 of a new class of NCS-free cyclometalated ruthenium(II) complexes, Ru(tctpy)(O<^>N<^>C) (where O<^>N<^>C is a tridentate 6-phenylpyridine-2-carboxylate), were synthesized for use as near-infrared (IR) sensitizers in dye-sensitized solar cells (DSSCs). A tridentate donor ligand, 6-phenylpyridine-2-carboxylate was introduced in order to enhance the light harvesting efficiency in the longer wavelength region for the first time. Modifying the ligand improved the photovoltaic performance, and DSSCs sensitized with FT117 exhibited efficient panchromatic sensitization over the entire visible wavelength, extending into the near-IR region. The highest incident photon-to-current conversion efficiency (68%) was found at 600 nm, and the action spectrum onset was near 920 nm. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.inoche.2014.05.022

文献信息

• [EN] A TAUTOMERIC LIGAND ENABLES BIOMIMETIC C-H HYDROXYLATION WITH MOLECULAR OXYGEN<br/>[FR] LIGAND TAUTOMÈRE PERMETTANT UNE HYDROXYLATION C-H BIOMIMÉTIQUE AVEC DE L'OXYGÈNE MOLÉCULAIRE
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2022125736A1

  公开（公告）日：2022-06-16

  Disclosed herein is a process for making a compound of formula (2) by (hetero)aromatic C-H hydroxylation of a compound of formula (1): catalyzed by palladium(II) and a bidentate ligand in the presence of O2. The process is useful for instance, in the late-stage modification of medicinally important heterocycles.

  本文公开了一种通过(杂)芳基C-H羟基化化合物的公式(1)制备公式(2)的过程：在氧气存在下，钯(II)和双齿配体催化。该过程在药物重要杂环的后期修饰中非常有用。
• JP2015/13928
  申请人：——

  公开号：——

  公开（公告）日：——
• A tautomeric ligand enables directed C‒H hydroxylation with molecular oxygen
  作者：Zhen Li、Zhen Wang、Nikita Chekshin、Shaoqun Qian、Jennifer X. Qiao、Peter T. Cheng、Kap-Sun Yeung、William R. Ewing、Jin-Quan Yu

  DOI：10.1126/science.abg2362

  日期：2021.6.25

  challenging when oxygen is used as the oxidant. Here, we report a palladium complex bearing a bidentate pyridine/pyridone ligand that efficiently catalyzes this reaction at ring positions adjacent to carboxylic acids. Infrared, x-ray, and computational analysis support a possible role of ligand tautomerization from mono-anionic (L,X) to neutral (L,L) coordination in the catalytic cycle of aerobic carbon–hydrogen

  当使用氧气作为氧化剂时，使用过渡金属催化剂对芳基碳氢键进行羟基化已被证明具有挑战性。在这里，我们报告了一种钯配合物，它带有双齿吡啶/吡啶酮配体，可在与羧酸相邻的环位置有效地催化该反应。红外、X 射线和计算分析支持从单阴离子 (L,X) 到中性 (L,L) 配位的配体互变异构在好氧碳氢羟基化反应的催化循环中的可能作用。由杂环决定的传统位点选择性被这种催化剂推翻，从而允许在以前无法接近的位点对药物感兴趣的化合物进行后期修饰。
• New class of NCS-free cyclometalated ruthenium(II) complexes with 6-phenylpyridine-2-carboxylate for use as near-infrared sensitizers in dye-sensitized solar cells
  作者：Takashi Funaki、Hiromi Otsuka、Nobuko Onozawa-Komatsuzaki、Kazuyuki Kasuga、Kazuhiro Sayama、Hideki Sugihara

  DOI：10.1016/j.inoche.2014.05.022

  日期：2014.8

  Three examples, FT102, FT90, and FT117 of a new class of NCS-free cyclometalated ruthenium(II) complexes, Ru(tctpy)(O<^>N<^>C) (where O<^>N<^>C is a tridentate 6-phenylpyridine-2-carboxylate), were synthesized for use as near-infrared (IR) sensitizers in dye-sensitized solar cells (DSSCs). A tridentate donor ligand, 6-phenylpyridine-2-carboxylate was introduced in order to enhance the light harvesting efficiency in the longer wavelength region for the first time. Modifying the ligand improved the photovoltaic performance, and DSSCs sensitized with FT117 exhibited efficient panchromatic sensitization over the entire visible wavelength, extending into the near-IR region. The highest incident photon-to-current conversion efficiency (68%) was found at 600 nm, and the action spectrum onset was near 920 nm. (C) 2014 Elsevier B.V. All rights reserved.