2-(4-fluorophenyl)-5-nitropyridine | 886361-78-0

• 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
• 英文名称: 2-(4-fluorophenyl)-5-nitropyridine
• CAS: 886361-78-0
• 化学式: C₁₁H₇FN₂O₂
• mdl: MFCD06200966
• 分子量: 218.187
• InChiKey: IXAGUEHBMXZMNQ-UHFFFAOYSA-N

物化性质

• 熔点：
  132-136

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  2-(4-fluorophenyl)-5-nitropyridine 在 双氧水 、 palladium diacetate 、 eosin Y disodium salt 、 silver carbonate 作用下， 以 1,4-二氧六环 为溶剂， 以66 %的产率得到5-fluoro-2-(5-nitropyridin-2-yl)phenol
  参考文献：
  名称：

  H2O2 存在下可见光诱导钯催化含氮杂环芳烃的 CH 羟基化

  摘要：

  通过钯催化芳烃的 C H 羟基化，以氮杂环为导向基团，过氧化氢为羟基化试剂，开发了一种可见光诱导的酚类化合物合成策略。具有氮杂环导向基团的多种（杂）芳烃可在温和的反应条件下用于邻位CH羟基化，并以良好的收率合成了一系列酚类化合物。该方案具有良好的官能团耐受性和广泛的底物范围，已成功应用于天然产物卡波霉素和药物地拉罗司的合成。根据实验结果和文献调查，光诱导 C 的激进机制提出了 H 羟基化。该方案为通过CH键活化羟基化制备酚类化合物提供了一种新的解决方案。

  DOI：

  10.1016/j.tetlet.2022.154225
• 作为产物：
  描述：

  2-氯-5-硝基吡啶 、 (对氟苯基)3Bi 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 4.0h， 以73%的产率得到2-(4-fluorophenyl)-5-nitropyridine
  参考文献：
  名称：

  Cross-coupling study of iodo/chloropyridines and 2-chloroquinoline with atom-economic triarylbismuth reagents under Pd-catalysis

  摘要：

  This study describes the palladium-catalyzed couplings of iodopyridines, chloropyridines, and chloroquinoline with atom-economic BiAr3 reagents in sub-stoichiometric loadings. Mono-arylations of iodo and chloropyridines produced arylpyridines in high yields. The couplings addressed with dihalopyridines have afforded chemo- and regio-selective coupling products. Arylations of 2-chloroquinoline with different triarylbismuth reagents demonstrated fruitful coupling reactivity under the established conditions. This sumptuous study demonstrates the remarkable cross-coupling reactivity of iodo/chloropyridines and chloroquinoline with triarylbismuth reagents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.11.036

文献信息

• A Zwitterionic Palladium(II) Complex as a Precatalyst for Neat-Water-Mediated Cross-Coupling Reactions of Heteroaryl, Benzyl, and Aryl Acid Chlorides with Organoboron Reagents
  作者：Visannagari Ramakrishna、Morla Jhansi Rani、Nareddula Dastagiri Reddy

  DOI：10.1002/ejoc.201701241

  日期：2017.12.29

  A zwitterionic palladium(II) complex has been found to be an efficient catalyst for Suzuki–Miyaura cross‐coupling reactions of aryl and heteroaryl organoboron reagents with various heteroaryl chlorides, aryl‐ and heteroarylmethyl chlorides, and aryl acid chlorides in neat water.

  两性离子钯（II）络合物是在纯净水中使芳基和杂芳基有机硼试剂与各种杂芳基氯化物，芳基和杂芳基甲基氯化物以及芳基酰氯发生铃木–宫浦交叉偶联反应的有效催化剂。
• [EN] PHTHALIMIDE DERIVATIVES AS MODULATORS OF WNT PATHWAY<br/>[FR] DÉRIVÉS DE PHTALIMIDE À TITRE DE MODULATEURS DE LA VOIE WNT
  申请人：AGENCY SCIENCE TECH & RES

  公开号：WO2015187094A1

  公开（公告）日：2015-12-10

  The present invention relates to compounds of formula (I), [Formula should be inserted here] pharmaceutically acceptable salts, solvates and polymorphs thereof, including all tautomers and stereoisomers thereof, wherein R1 is alkyl; alkoxy-alkyl-; carbocyclyl; heterocyclyl; aryl; heteroaryl; aryl-alkyl-; heteroaryl- alkyl-; carbocyclyl-alkyl-; or heterocyclyl-alkyl-; R2 is H or alkyl; R3 is H or alkyl; Y is aryl; heteroaryl; carbocyclyl; or heterocyclyl; and Z is aryl; heteroaryl; carbocyclyl; or heterocyclyl.

  本发明涉及化合物的公式（I），其药学上可接受的盐、溶剂和多型体，包括其所有互变异构体和立体异构体，其中R1是烷基；烷氧基烷基；碳环烷基；杂环烷基；芳基；杂芳基；芳基烷基；杂芳基烷基；碳环烷基烷基；或杂环烷基烷基；R2是H或烷基；R3是H或烷基；Y是芳基；杂芳基；碳环烷基；或杂环烷基；Z是芳基；杂芳基；碳环烷基；或杂环烷基。
• Ni-Catalyzed C–H Cyanation of (Hetero)arenes with 2-Cyanoisothiazolidine 1,1-Dioxide as a Cyanation Reagent
  作者：Junjie Ma、Hao Liu、Xin He、Zhicheng Chen、Yue Liu、Chuanfu Hou、Zhizhong Sun、Wenyi Chu

  DOI：10.1021/acs.orglett.1c00468

  日期：2021.4.16

  A nickel-catalyzed C–H cyanation reaction of arenes has been developed using 2-cyanoisothiazolidine 1,1-dioxide as an electrophilic cyanation reagent. Many different directing groups can be used in this cyanation to obtain a series of cyanation products with good yields. Adopting this strategy to introduce a cyano group, natural alkaloid menisporphine was successfully synthesized through cyano group

  使用2-氰基异噻唑烷1，1-二氧化物作为亲电子氰化试剂已开发出镍催化的芳烃的CH氰化氰化反应。在该氰化反应中可以使用许多不同的导向基团，以获得具有良好收率的一系列氰化反应产物。采用这种引入氰基的策略，通过氰基的转化成功合成了天然生物碱半胱氨酸，进一步证明了该氰化方法的实用性。
• [EN] MALEIMIDE DERIVATIVES AS MODULATORS OF WNT PATHWAY<br/>[FR] DÉRIVÉS DE MALÉIMIDE COMME MODULATEURS D'UNE VOIE WNT
  申请人：AGENCY SCIENCE TECH & RES

  公开号：WO2015094118A1

  公开（公告）日：2015-06-25

  The present invention relates to compounds of formula (I), combinations and uses thereof for disease therapy, or a pharmaceutically acceptable salt, solvate or polymorph therof, including all tautomers and stereoisomers thereof wherein R1represents optionally substituted alkyl (wherein optional substituents include one or more substituents each independently selected from C1-6alkoxy); optionally substituted carbocyclyl (wherein optional substituents include one or more substituents each independently selected from C1-6alkyl, C1-6alkoxy, C1-6haloalkyl, C1-6haloalkoxy and halo); or -alkylaryl; R2 represents H; or alkyl; R3 represents H; or alkyl; U, V and W represent -(CH2)-; or U and V together represent -CH=CH- and W represents C=O; Y represents aryl; heteroaryl; optionally substituted carbocyclyl (wherein optional substituents include one or more substituents each independently selected from C1-6alkyl, C1-6alkoxy, C1-6haloalkyl, C1-6haloalkoxy and halo); or optionally substituted heterocyclyl (wherein optional substituents include one or more substituents each independently selected from C1-6alkyl, C1-6 alkoxy, -C(O)OC1-6alkyl, -C(O)C1-6alkyl and-C(O)NHC1-6alkyl); and Z represents aryl; heteroaryl; optionally substituted carbocyclyl (wherein optional substituents include one or more substituents each independently selected from C1-6alkyl, C1-6alkoxy, C1- 6haloalkyl, C1-6haloalkoxy and halo); or optionally substituted heterocyclyl (wherein optional substituents include one or more substituents each independently selected from C1-6alkyl, C1-6. alkoxy, -C(O)OC1-6alkyl, -C(O)C1-6alkyl and -C(O)NHC1-6alkyl).

  本发明涉及式(I)的化合物，其组合物和用于疾病治疗的用途，或其药学上可接受的盐，溶剂或多晶体，包括其所有互变异构体和立体异构体，其中R1代表可选取代的烷基（其中可选取代基包括一个或多个从C1-6烷氧基中独立选择的基团）；可选取代的碳环烷基（其中可选取代基包括一个或多个从C1-6烷基，C1-6烷氧基，C1-6卤代烷基，C1-6卤代烷氧基和卤素中独立选择的基团）；或-烷基芳基；R2代表H；或烷基；R3代表H；或烷基；U，V和W代表-(CH2)-；或U和V组成-CH=CH-，而W代表C=O；Y代表芳基；杂芳基；可选取代的碳环烷基（其中可选取代基包括一个或多个从C1-6烷基，C1-6烷氧基，C1-6卤代烷基，C1-6卤代烷氧基和卤素中独立选择的基团）；或可选取代的杂环烷基（其中可选取代基包括一个或多个从C1-6烷基，C1-6烷氧基，-C（O）OC1-6烷基，-C（O）C1-6烷基和-C（O）NHC1-6烷基中独立选择的基团）；而Z代表芳基；杂芳基；可选取代的碳环烷基（其中可选取代基包括一个或多个从C1-6烷基，C1-6烷氧基，C1-6卤代烷基，C1-6卤代烷氧基和卤素中独立选择的基团）；或可选取代的杂环烷基（其中可选取代基包括一个或多个从C1-6烷基，C1-6烷氧基，-C（O）OC1-6烷基，-C（O）C1-6烷基和-C（O）NHC1-6烷基中独立选择的基团）。
• [DE] SUBSTITUIERTE 2-ARYLPYRIDINE ALS HERBIZIDE<br/>[EN] SUBSTITUTED 2-ARYLPYRIDINE AS HERBICIDE<br/>[FR] ARYLPYRIDINE SUBSTITUEE EN 2 UTILISEE COMME HERBICIDE
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：WO1998007720A1

  公开（公告）日：1998-02-26

  (DE) Substituierte 2-Arylpyridine (I) und deren Salze, wobei R1 = SH, SO2OH, SO2C1, SO2NH2, C1-C6-Alkylthio, C1-C6-Alkylsulfinyl, C1-C6-Alkylsulfonyl, C1-C6-Alkylaminosulfonyl, Di(C1-C6-alkyl)aminosulfonyl; R2, R3 = H, Halogen; R4 = H, C1-C6-Alkyl, C1-C6-Halogenalkyl, Cyano-C1-C6-alkyl, C1-C6-Alkoxy, C1-C6-Alkoxy-C1-C6-alkyl, C1-C4-Halogenalkoxy-C1-C4-alkyl, C1-C6-Alkylthio-C1-C6-alkyl, C1-C6-Alkylsulfinyl-C1-C6-alkyl, C1-C6-Alkylsulfonyl-C1-C6-alkyl, C1-C4-Alkoxy-C1-C4-alkoxy-C1-C4-alkyl, C1-C6-Alkoxycarbonyl-C1-C6-alkyl, C1-C3-Alkoxy-C1-C3-alkoxycarbonyl-C1-C6-alkyl, C2-C4-Alkenyloxy-C1-C4-alkyl, C3-C4-Alkinyloxy-C1-C4-alkyl, C3-C7-Cycloalkyl, C3-C7-Cycloalkyl-C1-C6-alkyl, C3-C7-Cycloalkyloxy-C1-C6-alkyl, C3-C7-Cycloalkylthio-C1-C6-alkyl, C3-C8-Alkenyl, C3-C8-Alkinyl, C3-C8-Halogenalkenyl, C3-C8-Halogenalkinyl, C1-C6-Alkoxy-C3-C8-alkenyl, C1-C6-alkoxy-C3-C8-alkinyl, C1-C6-Alkylcarbonyl, C1-C6-Alkylsulfonyl, C3-C6-Alkenyloxy, C3-C6-Alkinyloxy oder geg. subst. Benzyl; X = -O-, -S-, -NH-, -N(CH3)-, -CH2-; Y = chemische Bindung, -CO-, C(R5,R6); R5,R6 = H, NO2, CN, OCH3, SCH3, Halogen, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxycarbonyl, C2-C6-Alkenyl, C3-C6-Alkinyl, C1-C4-Alkoxycarbonyl-C1-C4-alkyl. Verwendung: als Herbizide; zur Desikkation/Defoliation von Pflanzen.(EN) Substituted 2-arylpyridine of formula (I) and salts thereof. In said formula (I), R1 = SH, SO2OH, SO2C1, SO2NH2, C1-C6-Alkylthio, C1-C6-Alkyl sulfinyl, C1-C6-alkylsulfonyl, C1-C6-alkylamino-sulfonyl, Di(C1-C6-alkyl)aminosulfonyl; R2, R3 = H, halogen; R4 = H, C1-C6-alkyl, C1-C6-halogenalkyl, cyano-C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C4-halogen-alkoxy-C1-C4-alkyl, C1-C6-alkylthio-C1-C6-alkyl, C1-C6 alkyl sulfinyl-C1-C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4-alkyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C3-alkoxy-C1-C3-alkoxycarbonyl-C1-C6-alkyl, C2-C4-alkenyloxy-C1-C4-alkyl, C3-C4-alkinyloxy-C1-C4-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl, C3-C7-cycloalkyloxy-C1-C6-alkyl, C3-C7-cycloalkylthio-C1-C6-alkyl, C3-C8-alkenyl, C3-C8-alkinyl, C3-C8-halogenalkenyl, C3-C8-halogenalkinyl, C1-C6-alkoxy-C3-C8-alkenyl, C1-C6-alkoxy-C3-C8-alkinyl, C1-C6-alkylcarbonyl, C1-C6-alkylsulfonyl, C3-C6-alkenyloxy, C3-C6-alkinyloxy or eventually substituted benzyl; X = -O-, -S-, -NH-, -N(CH3)-, -CH2-; Y = chemical bond, -CO-, C(R5,R6); R5,R6 = H, NO2, CN, OCH3, SCH3, halogen, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxycarbonyl, C2-C6-alkenyl, C3-C6-alkinyl, C1-C4-alkoxycarbonyl-C1-C4-alkyl. Application as herbicide; for plant desiccation/defoliation.(FR) Arylpyridine substituée en 2 répondant à la formule (I) et ses sels. Dans ladite formule (I), R1 = SH, SO2OH, SO2C1, SO2NH2, C1-C6-Alkylthio, C1-C6-Alkyle sulfinyle, C1-C6-alkylsulfonyle, C1-C6-alkylamino-sulfonyle, Di(C1-C6-alkyl)aminosulfonyle; R2, R3 = H, halogène; R4 = H, C1-C6-alkyle, C1-C6-halogenalkyle, cyano-C1-C6-alkyle, C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkyle, C1-C4-halogène-alkoxy-C1-C4-alkyle, C1-C6-alkylthio-C1-C6-alkyle-, C1-C6-alkylsulfinyle-C1-C6-alkyle, C1-C6-alkylsulfonyl-C1-C6 alkyle, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4-alkyle, C1-C6-alkoxycarbonyle-C1-C6-alkyle, C1-C3-alkoxy-C1-C3-alkoxycarbonyl-C1-C6-alkyle, C2-C4-alkenyloxy-C1-C4-alkyle, C3-C4-alkinyloxy-C1-C4-alkyle, C3-C7-cycloalkyle, C3-C7-cycloalkyl-C1-C6-alkyle, C3-C7-cycloalkyloxy-C1-C6-alkyle, C3-C7-cycloalkylthio-C1-C6-alkyle, C3-C8-alkenyle, C3-C8-alkinyle, C3-C8-halogenalkenyle, C3-C8-halogenalkinyle, C1-C6-alkoxy-C3-C8-alkenyle, C1-C6-alkoxy-C3-C8-alkinyle, C1-C6-alkylcarbonyle, C1-C6-alkylsulfonyle, C3-C6-alkenyloxy, C3-C6-alkinyloxy ou benzyl éventuellement substitué; X = -O-, -S-, -NH-, -N(CH3)-, -CH2-; Y = liaison chimique, -CO-, C(R5,R6); R5,R6 = H, NO2, CN, OCH3, SCH3, halogène, C1-C4-alkyle, C1-C4-halogenalkyle, C1-C4-alkoxycarbonyle, C2-C6-alkenyle, C3-C6-alkinyle, C1-C4-alkoxycarbonyl-C1-C4-alkyle. Application: comme herbicide; pour la dessication/défoliation des plantes.

  ( DE ) Substituierte 2-Arylpyridine ( I ) und deren Salze , wobei R1 = SH , SO2OH , SO2C1 , SO2NH2 , C1-C6-Alkylthio , C1-C6-Alkylsulfinyl , C1-C6-Alkylsulfonyl , C1-C6-Alkylaminosulfonyl , Di(C1-C6-alkyl)aminosulfonyl ; R2 , R3 = H , Halogen ; R4 = H , C1-C6-Alkyl , C1-C6-Halogenalkyl , Cyano-C1-C6-alkyl , C1-C6-Alkoxy , C1-C6-Alkoxy-C1-C6-alkyl , C1-C4-Halogenalkoxy-C1-C4-alkyl , C1-C6-Alkylthio-C1-C6-alkyl , C1-C6-Alkylsulfinyl-C1-C6-alkyl , C1-C6-Alkylsulfonyl-C1-C6-alkyl , C1-C4-Alkoxy-C1-C4-alkoxy-C1-C4-alkyl , C1-C6-Alkoxycarbonyl-C1-C6-alkyl , C1-C3-Alkoxy-C1-C3-alkoxycarbonyl-C1-C6-alkyl , C2-C4-Alkenyloxy-C1-C4-alkyl , C3-C4-Alkinyloxy-C1-C4-alkyl , C3-C7-Cycloalkyl , C3-C7-Cycloalkyl-C1-C6-alkyl , C3-C7-Cycloalkyloxy-C1-C6-alkyl , C3-C7-Cycloalkylthio-C1-C6-alkyl , C3-C8-Alkenyl , C3-C8-Alkinyl , C3-C8-Halogenalkenyl , C3-C8-Halogenalkinyl , C1-C6-Alkoxy-C3-C8-Alkenyl , C1-C6-Alkoxy-C3-C8-Alkinyl , C1-C6-Alkylcarbonyl , C1-C6-Alkylsulfonyl , C3-C6-Alkenyloxy , C3-C6-Alkinyloxy oder geg. substit. Benzyl ; X = -O- , -S- , -NH- , -N(CH3)- , -CH2- ; Y = chemische Bindung , -CO- , C(R5,R6) ; R5,R6 = H , NO2 , CN , OCH3 , SCH3 , Halogen , C1-C4-Alkyl , C1-C4-Halogenalkyl , C1-C4-Alkoxycarbonyl , C2-C6-Alkenyl , C3-C6-Alkinyl , C1-C4-Alkoxycarbonyl-C1-C4-alkyl. Benutzung: als Herbicide ; zur Entsechung/Ent.Decimalisierung von Pflanzen. ( EN ) Substituted 2-arylpyridine of formula ( I ) and its salts. In formula ( I ), R1 = SH , SO2OH , SO2C1 , SO2NH2 , C1-C6-alkylthio , C1-C6-alkyl sulfinyl , C1-C6-alkylsulfonyl , C1-C6-alkylaminosulfonyl , Di(C1-C6-alkyl)aminosulfonyl ; R2 , R3 = H , halogen ; R4 = H , C1-C6-alkyl , C1-C6-halogenalkyl , cyano-C1-C6-alkyl , C1-C6-alkoxy , C1-C6-alkoxy-C1-C6-alkyl , C1-C4-halogen-alkoxy-C1-C4-alkyl , C1-C6-alkylthio-C1-C6-alkyl , C1-C6-alkylsulfinyl-C1-C6-alkyl , C1-C6-alkylsulfonyl-C1-C6-alkyl , C1-C4-alkoxy-C1-C4-alkoxy-C1-C4-alkyl , C1-C6-alkoxycarbonyl-C1-C6-alkyl , C1-C3-alkoxy-C1-C3-alkoxycarbonyl-C1-C6-alkyl , C2-C4-alkenyloxy-C1-C4-alkyl , C3-C4-alkinyloxy-C1-C4-alkyl , C3-C7-cycloalkyl , C3-C7-cycloalkyl-C1-C6-alkyl , C3-C7-cycloalkyloxy-C1-C6-alkyl , C3-C7-cycloalkylthio-C1-C6-alkyl , C3-C8-alkenyl , C3-C8-alkinyl , C3-C8-halogenalkenyl , C3-C8-halogenalkinyl , 1-C6-alkoxy-C3-C8-alkenyl , 1-C6-alkoxy-C3-C8-alkinyl , 1-C6-alkylcarbonyle , 1-C6-alkylsulfonyl , C3-C6-alkenyloxy , C3-C6-alkinyloxy or eventually substitute benzyl ; X = -O- , -S- , -NH- , -N(CH3)- , -CH2- ; Y = chemical bond , -CO- , C(R5,R6) ; R5,R6 = H , NO2 , CN , OCH3 , SCH3 , halogen , C1-C4-alkyl , C1-C4-halogenalkyl , C1-C4-alkoxycarbonyl , C2-C6-alkenyl , C3-C6-alkinyl , C1-C4-alkoxycarbonyl-C1-C4-alkyl. Application: as herbicide ; for plant desiccation/defoliation.