3-phenoxypyridine 1-oxide | 32967-12-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-phenoxypyridine 1-oxide
• 英文别名: 3-Phenoxy-pyridin-1-oxid；1-Oxido-3-phenoxypyridin-1-ium
• CAS: 32967-12-7
• 化学式: C₁₁H₉NO₂
• 分子量: 187.198
• InChiKey: CQCJWARBGJHIHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 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：
  34.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-phenoxypyridine 1-oxide 在 bis-triphenylphosphine-palladium(II) chloride 、 溶剂黄146 、 silver(l) oxide 作用下， 反应 24.0h， 以65%的产率得到benzofuro[3,2-b]pyridine 1-oxide
  参考文献：
  名称：

  Synthesis of Benzofuro[3,2-b]pyridines via Palladium-Catalyzed Dual C–H Activation of 3-Phenoxypyridine 1-Oxides

  摘要：

  An efficient oxidative cyclization to straightforward synthesis of benzofuro[3,2-b]pyridine 1-oxides with high regioselectivity via Pd-catalyzed intramolecular dual C-H activation was developed. The resulting products could be deoxygenated easily to the corresponding benzofuro[3,2-b]pyridines in excellent yields.

  DOI：

  10.1021/ol5033464
• 作为产物：
  描述：

  苯酚 在 copper(l) iodide 、 2,2,6,6-四甲基-3,5-庚二酮 、 caesium carbonate 、 间氯过氧苯甲酸 作用下， 以 N-甲基吡咯烷酮 、 氯仿 为溶剂， 反应 24.67h， 生成 3-phenoxypyridine 1-oxide
  参考文献：
  名称：

  Synthesis of Benzofuro[3,2-b]pyridines via Palladium-Catalyzed Dual C–H Activation of 3-Phenoxypyridine 1-Oxides

  摘要：

  An efficient oxidative cyclization to straightforward synthesis of benzofuro[3,2-b]pyridine 1-oxides with high regioselectivity via Pd-catalyzed intramolecular dual C-H activation was developed. The resulting products could be deoxygenated easily to the corresponding benzofuro[3,2-b]pyridines in excellent yields.

  DOI：

  10.1021/ol5033464

文献信息

• MODULATORS OF GLUCOCORTICOID RECEPTOR, AP-1, AND/OR NF-kB ACTIVITY AND USE THEREOF
  申请人：Weinstein David S.

  公开号：US20090075995A1

  公开（公告）日：2009-03-19

  Novel non-steroidal compounds are provided which are useful in treating diseases associated with modulation of the glucocorticoid receptor, AP-1, and/or NF-κB activity, including inflammatory and immune diseases, having the structure of formula (I): an enantiomer, diastereomer, or tautomer thereof, or a prodrug ester thereof, or a pharmaceutically-acceptable salt thereof, in which: Z is heterocyclo or heteroaryl; A is a 5- to 8-membered carbocyclic ring or a 5- to 8-membered heterocyclic ring; B is a cycloalkyl, cycloalkenyl, aryl, heterocyclo, or heteroaryl ring, wherein each ring is fused to the A ring on adjacent atoms and optionally substituted by one to four groups which are the same or different and are independently selected from R 5 , R 6 , R 7 , and R 8 ; J 1 , J 2 , and J 3 are at each occurrence the same or different and are independently -A 1 QA 2 -; Q is a bond, O, S, S(O), or S(O) 2 ; A 1 and A 2 are the same or different and are at each occurrence independently selected from a bond, C 1-3 alkylene, substituted C 1-3 alkylene, C 2-4 alkenylene, and substituted C 2-4 alkenylene, provided that A 1 and A 2 are chosen so that ring A is a 5- to 8-membered carbocyclic or heterocyclic ring; R 1 to R 11 are as defined herein. Also provided are pharmaceutical compositions and methods of treating inflammatory- or immune-associated diseases and obesity and diabetes employing said compounds.

  提供了一系列新颖的非甾体化合物，这些化合物在治疗与糖皮质激素受体、AP-1和/或NF-κB活性调节相关的疾病中很有用，包括炎性和免疫疾病，具有以下结构式（I）： 其对应的光学异构体、对映异构体或互变异构体，或其前药酯，或其药用可接受盐，其中： Z是杂环或杂芳基； A是一个5至8成员的碳环或一个5至8成员的杂环； B是一个环烷基、环烯基、芳基、杂环或杂芳基环，其中每个环都与A环上的相邻原子融合，并且可以选择性地被一个到四个独立选自R5、R6、R7和R8的相同或不同的组取代； J1、J2和J3每次出现时相同或不同，独立地选自-A1QA2-；Q是键、O、S、S(O)或S(O)2；A1和A2相同或不同，每次出现时独立地选自键、C1-3烷基、取代的C1-3烷基、C2-4烯基和取代的C2-4烯基，前提是A1和A2的选择使得环A是一个5至8成员的碳环或杂环； R1至R11如本文所述定义。 还提供了使用这些化合物的药物组合物和治疗炎性疾病、免疫相关疾病、肥胖和糖尿病的方法。
• Mild, General, and Regioselective Synthesis of 2-Aminopyridines from Pyridine N-Oxides via N-(2-Pyridyl)pyridinium Salts
  作者：Hui Xiong、Adam T. Hoye

  DOI：10.1055/s-0040-1719865

  日期：2022.3

  2-aminopyridines from pyridine N-oxides via their corresponding N-(2-pyridyl)pyridinium salts has been demonstrated and investigated. The reaction sequence features a highly regioselective conversion of the N-oxide into its pyridinium salt followed by hydrolytic decomposition of the pyridinium moiety to furnish the 2-aminopyridine product. The method is compatible with a wide range of functional groups, is

  已经证明和研究了从吡啶N-氧化物通过其相应的N- (2-吡啶基)吡啶鎓盐合成 2-氨基吡啶。该反应序列的特征在于将N-氧化物高度区域选择性地转化为其吡啶鎓盐，然后将吡啶鎓部分水解分解以提供 2-氨基吡啶产物。该方法与广泛的官能团兼容，具有可扩展性，并且具有廉价试剂的特点。15 N-标记结果给出了与 Zincke 反应机制一致的产品。
• 3-Phenoxypyridine 1-oxides as anticonvulsant agents
  作者：Michael R. Pavia、Charles P. Taylor、Fred M. Hershenson、Sandra J. Lobbestael、Donald E. Butler

  DOI：10.1021/jm00399a027

  日期：1988.4

  The anticonvulsant activity of a series of 3-phenoxypyridine 1-oxides is described. An investigation carried out to optimize the activity/side effect ratio provided 4-methyl-3-phenoxypyridine 1-oxide, 3, as the derivative of choice. Overall, 3 has a pharmacological profile that is very similar to phenytoin. It exhibited significant anticonvulsant activity at doses that did not produce ataxia or sedation but caused increased spontaneous behavioral activity not seen with most anticonvulsants. The short duration of pharmacological effect of 3 was attributed to metabolic hydroxylation at the C-4 pyridine methyl group; however, structural modifications designed to inhibit this metabolic pathway were unsuccessful.
• VILLANI F. J.; MANN T. A.; WEFER E. A.; HANNON J.; LARCA L. L.; LANDON M.+, J. MED. CHEM. <JMCM-AR>, 1975, 18, NO 1, 1-8
  作者：VILLANI F. J.、 MANN T. A.、 WEFER E. A.、 HANNON J.、 LARCA L. L.、 LANDON M.+

  DOI：——

  日期：——
• PAVIA, MICHAEL R.;TAYLOR, CHARLES P.;HERSHENSON, FRED M.;LOBBESTAEL, SAND+, J. MED. CHEM., 31,(1988) N 4, 841-847
  作者：PAVIA, MICHAEL R.、TAYLOR, CHARLES P.、HERSHENSON, FRED M.、LOBBESTAEL, SAND+

  DOI：——

  日期：——