6-(4-甲氧基苯基)吡啶甲酸 | 86696-70-0

• 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-甲氧基苯基)吡啶甲酸
• 英文名称: 6-(4-methoxyphenyl)-2-pyridinecarboxylic acid
• 英文别名: 6-(4-Methoxyphenyl)picolinic acid；6-(4-methoxyphenyl)pyridine-2-carboxylic acid
• CAS: 86696-70-0
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: AKGIUKXMBSFGMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  6-(4-甲氧基苯基)吡啶甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 6-(4-methoxyphenyl)-N-(2H-tetrazol-5-yl)pyridine-2-carboxamide
  参考文献：
  名称：

  Antiallergic agents. 2. N-(1H-Tetrazol-5-yl)-6-phenyl-2-pyridinecarboxamides

  摘要：

  A new series of N-(1H-tetrazol-5-yl)-6-phenyl-2-pyridinecarboxamides was prepared to determine the effects of substituents on the benzene and pyridine rings on antiallergic activity in the rat passive cutaneous anaphylaxis (PCA) assay after oral administration. One member of this series, N-(1H-tetrazol-5-yl)-4-methyl-6-[4-(methylamino)-phenyl]-2- pyridinecarboxamide (231), has an ED50 value of 0.8 mg/kg po and is 85 times more potent than disodium cromoglycate (DSCG) on intravenous administration. Further evaluation of 231 as a clinically useful antiallergic agent is in progress.

  DOI：

  10.1021/jm00364a026
• 作为产物：
  描述：

  methyl 6-(4-methoxyphenyl)picolinate 在 氢氧化钾 作用下， 反应 1.0h， 生成 6-(4-甲氧基苯基)吡啶甲酸
  参考文献：
  名称：

  Antiallergic agents. 2. N-(1H-Tetrazol-5-yl)-6-phenyl-2-pyridinecarboxamides

  摘要：

  A new series of N-(1H-tetrazol-5-yl)-6-phenyl-2-pyridinecarboxamides was prepared to determine the effects of substituents on the benzene and pyridine rings on antiallergic activity in the rat passive cutaneous anaphylaxis (PCA) assay after oral administration. One member of this series, N-(1H-tetrazol-5-yl)-4-methyl-6-[4-(methylamino)-phenyl]-2- pyridinecarboxamide (231), has an ED50 value of 0.8 mg/kg po and is 85 times more potent than disodium cromoglycate (DSCG) on intravenous administration. Further evaluation of 231 as a clinically useful antiallergic agent is in progress.

  DOI：

  10.1021/jm00364a026

文献信息

• Self-Supported Heterogeneous Star-Shaped Oxime-Palladacycle Catalysts for the Suzuki Coupling Reactions
  作者：Ying-Chun Chen、Jin-Gen Deng、Qing-Ping Liu、Yong Wu、Jin Zhu

  DOI：10.1055/s-2006-941585

  日期：2006.6

  A novel strategy to synthesize heterogeneous star-shaped oxime-palladacycle catalysts, which exhibited good catalytic activity and recyclability in the Suzuki coupling of aryl bromides and chlorides, was described.

  报道了一种合成异质星形肟钯配位催化剂的新策略，该催化剂在溴代和氯代芳烃的Suzuki偶联反应中展现出良好的催化活性和可循环性。
• 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。
• [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。
• PYRAZOLE DERIVATIVES AND THEIR USE AS PKA AND PKB MODULATORS
  申请人：Astex Therapeutics Limited

  公开号：EP1919875A2

  公开（公告）日：2008-05-14
• [EN] PHARMACEUTICAL COMPOUNDS<br/>[FR] COMPOSES PHARMACEUTIQUES
  申请人：ASTEX THERAPEUTICS LTD

  公开号：WO2006136829A2

  公开（公告）日：2006-12-28

  [EN] The invention provides a compound of the formula (I) or a salt, solvate, tautomer or N-oxide thereof; wherein A is a saturated hydrocarbon linker group; E is a monocyclic or bicyclic carbocyclic or heterocyclic group; L¹ is a bond or a linker selected from C₁-C₄ alkenylene, C₁-C₄ alkynylene, -CONR', -NR'CO, -S, -C(O)-, -C(NR¹¹)-, -C(S)-, -N(R¹¹)₂, C(=CHR¹¹), -SO- and -SO_2-; or L¹ together with t R¹⁶ forms and 8-12 membered fused bicyclic heteroaryl ring system; L³ is a bond or a linker selected from CONH and HNCO; provided that L¹ and L³ cannot both be linkers simultaneously; and provided also that L¹ and L³ cannot both be a bond simultaneously; R¹⁶ is an optionally substituted 5- to 12-membered monocyclic or bicyclic carbocyclic or heterocyclic ring; L² is absent or is a linker selected from C]-C4 alkylene, Ci-C4 alkenylene, Ci-C4 alkynylene, -CONR'-, -NR'CO-, -O-, -S-, -C(O)-, C(=CHR¹¹), C(S)-, -N(R¹¹)₂, C_3-4 cycloalkanediyl, -SO- and -SO2-; R¹⁷ is absent or is C_1-6 alkyl or an optionally substituted 5 to 12 membered carbocyclic or heterocyclic ring; provided that when R¹⁷ is absent, then L² is also absent; and R², R³, R⁴, R⁵, R¹¹ and R' are as defined in the claims.
  [FR] L'invention concerne un composé représenté par la formule générale (I) ou un sel, un solvate, un tautomère ou un N-oxyde de ce composé. Dans cette formule générale (I), A désigne un groupe de liaison hydrocarboné saturé; E désigne un groupe carbocyclique ou hétérocyclique monocyclique ou bicyclique; L¹ désigne une liaison ou un élément de liaison sélectionné parmi un groupe alcénylène C₁-C₄, alcynylène C₁-C₄, -CONR', -NR'CO-, -S-, -C(O)-, -C(NR¹¹)-, -C(S)-, -N(R¹¹)₂, C(=CHR¹¹), -SO- et -SO₂-; ou L¹ et le groupe R¹⁶ forment un système à noyau hétéroaryle bicyclique fusionné comportant 8 à 12 éléments; L³ désigne une liaison ou un élément de liaison sélectionné parmi CONH et HNCO; à condition que L¹ et L³ ne désignent pas des éléments de liaison en même temps; et également à condition que L¹ et L³ ne désignent pas une liaison en même temps; R¹⁶ désigne un noyau carbocyclique ou hétérocyclique monocyclique ou bicyclique comportant 5 à 12 éléments éventuellement substitué; L² désigne un élément absent ou un élément de liaison sélectionné parmi un groupe alkylène C₁-C₄, alcénylène C₁-C₄, alcynylène C₁-C₄, -CONR'-, -NR'CO-, -O-, -S-, -C(O)-, C(=CHR¹¹), C(S)-, -N(R¹¹)₂, cycloalkanediyle C_3-4, -SO- et -SO2-; R¹⁷ désigne un élément absent ou un groupe alkyle C₁-C₆ ou un noyau carbocyclique ou hétérocyclique comportant 5 à 12 éléments éventuellement substitué; à condition que lorsque R¹⁷ est absent, alors L² est également absent; et R², R³, R⁴, R⁵, R¹¹ et R' désignent des éléments définis dans les revendications.