3-methoxy-5-(phenylethynyl)pyridine | 866684-37-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methoxy-5-(phenylethynyl)pyridine
• 英文别名: 3-(phenylethynyl)-5-methoxypyridine；3-Methoxy-5-phenylethynylpyridine；3-methoxy-5-(2-phenylethynyl)pyridine
• CAS: 866684-37-9
• 化学式: C₁₄H₁₁NO
• 分子量: 209.247
• InChiKey: PQPFPGUHVLTKQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methoxy-5-(phenylethynyl)pyridine 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以4%的产率得到3-hydroxy-5-phenylethynylpyridine
  参考文献：
  名称：

  [EN] PYRIDYL DERIVATIVES AND THEIR USE AS MGLU5 RECEPTOR ANTAGONISTS
  [FR] DERIVES DE PYRIDYLE ET LEUR UTILISATION EN TANT QU'ANTAGONISTES DU RECEPTEUR DE MGLU5

  摘要：

  本发明涉及公式（I）的吡啶衍生物作为mGlu5受体拮抗剂。因此，这些化合物可能对通过拮抗mGlu5受体而得到缓解的疾病的治疗或预防有用，其中Ar是苯基或萘基，每种基可能被一个或多个C1-C4烷基，C1-C4烷氧基，C1-C5酰基，卤素，氨基，硝基，氰基，羟基，C1-C5酰胺基，C1-C4烷基磺酰胺基，单-，二-或三氟代的C1-C3烷基，取代基可能相同也可能不同，并且可能带有CONH2，CONHCH3，CON(CH3)2，CO2H，CO2CH3，OCF3，CH2NHCOCH3，CH2NH2，CH2N(CH3)2，CH2CN，CH2OH，CH2NHSO2CH3，CH2N(CH3)(CH2)2CN，CH2N(CH3)CH(CH3)2，CH2NHCH(CH3)2，CH2NH(CH2)2CH3，CH2NHCO2R4，CH2NHCH2CH3，CH2NHCH3 NHCOC(CH3)2或N(S(O)2CH3)2取代基；R1是氢，卤素，R4，CN，C(NOH)R3，C(NO-R4)R3，(CH)2CO2R4，(CH2)nOR3，COR3，CF3，SR4，S(O)R4，S(O)2R4，COCH2CO2R3，NHSO2R4，NHCOR3，C(NOR3)NH2，CH2OCOR3，(CH2)nNH2，CON(CH3)2(CH2)nNHCO2R4，CO2R3，CONH2，CSNH2，C(NH)NHOR3，(CH2)nN(CH3)2或CONHNHCOR3；R2是1,2-乙烯二基或1,2-乙炔二基；R3是氢或C1-C4烷基；R4是C1-C4烷基；n为0,1,2,3或4；或其药学上可接受的盐，或其N-氧化物。

  公开号：

  WO2005094822A1
• 作为产物：
  描述：

  3-溴-5-甲氧基吡啶 、 苯乙炔 在 bis(η3-allyl-μ-chloropalladium(II)) 、 1-n-butyl-3-methylimidazolium tetrafluoroborate 、 三苯基膦 、 四氢吡咯 作用下， 反应 4.0h， 以91%的产率得到3-methoxy-5-(phenylethynyl)pyridine
  参考文献：
  名称：

  Double Arylation of Diynes and Alkynylation of Functionalized Heteroaryl Halides by a Practical Heck Reaction in an Ionic Liquid

  摘要：

  在咪唑离子液体[BMIM][BF4]这种高极性非挥发性溶剂中，可以高效地催化富电子溴杂环戊烯的炔化反应，以及二炔（杂）芳基化反应。这种方法可以替代二恶烷、DMF、NMP 或 DMAc 等传统溶剂。新的炔烃是在一个包含无铜钯催化剂、三苯基膦配体和各种廉价碱的体系中形成的。报告中的炔分子是以高产率选择性合成的，而且大多是前所未有的。

  DOI：

  10.1055/s-0031-1289861

文献信息

• Phosphine-Free Palladium-Catalyzed Decarboxylative Coupling of Alkynylcarboxylic Acids with Aryl and Heteroaryl Halides
  作者：Police Vishnuvardhan Reddy、Pottabathula Srinivas、Manne Annapurna、Suresh Bhargava、Jorg Wagler、Nedaossadat Mirzadeh、Mannepalli Lakshmi Kantam

  DOI：10.1002/adsc.201200876

  日期：2013.3.11

  We herein report the design and development of a carboxyamido/carbene ligand and its Pd‐complex for the decarboxylative coupling of alkynylcarboxylic acids with aryl and heteroaryl halides to afford arylalkynes.

  我们在此报告了羧基酰胺基/卡宾配体及其Pd-络合物的设计和开发，用于炔基羧酸与芳基和杂芳基卤化物的脱羧偶联，从而得到芳基炔烃。
• Pyridyl Derivatives and Their Use as Mglu5 Antagonists
  申请人：Agejas-Chicharro Francisco Javier

  公开号：US20080194647A1

  公开（公告）日：2008-08-14

  The present invention is directed toward pyridyl derivatives of formula (I) as antagonists of the mGlu5 receptor. As such the compounds may be useful for treatment or prevention of disorders remedied by antagonism of the mGlu5 receptor, wherein Ar is phenyl or napthyl each of which may be substituted by one or more C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 5 acyl, halo, amino, nitro, cyano, hydroxy, C 1 -C 5 acylamino, C 1 -C 4 alkylsulfonylamino, mono-, di- or trifluorinated C 1 -C 3 alkyl, substituents which may be the same or different and may bear a CONH 2 , CONHCH 3 , CON(CH 3 ) 2 , CO 2 H, CO 2 CH 3 , OCF 3 , CH 2 NHCOCH 3 , CH 2 NH 2 , CH 2 N(CH 3 ) 2 , CH 2 CN, CH 2 OH, CH 2 NHSO 2 CH 3 , CH 2 N(CH 3 )(CH 2 ) 2 CN, CH 2 N(CH 3 )CH(CH 3 ) 2 , CH 2 NHCH(CH 3 ) 2 , CH 2 NH(CH 2 ) 2 CH 3 , CH 2 NHCO 2 R 4 , CH 2 NHCH 2 CH 3 , CH 2 NHCH 3 NHCOC(CH 3 ) 2 , or N(S(O) 2 CH 3 ) 2 substituent; R 1 is hydrogen, halo, R 4 , CN, C(NOH)R 3 , C(NO—R 4 )R 3 , (CH) 2 CO 2 R 4 , (CH 2 ) n OR 3 , COR 3 , CF 3 , SR 4 , S(O)R 4 , S(O) 2 R 4 , COCH 2 CO 2 R 3 , NHSO 2 R 4 , NHCOR 3 , C(NOR 3 )NH 2 , CH 2 OCOR 3 , (CH 2 ) n NH 2 , CON(CH 3 ) 2 (CH 2 ) n NHCO 2 R 4 , CO 2 R 3 , CONH 2 , CSNH 2 , C(NH)NHOR 3 , (CH 2 ) n N(CH 3 ) 2 , or CONHNHCOR 3 ; R 2 is 1,2-ethenediyl or 1,2-ethynediyl; R 3 is hydrogen or C 1 -C 4 alkyl; R 4 is C 1 -C 4 alkyl; and n is 0, 1, 2, 3 or 4; or a pharmaceutically acceptable salt thereof, or an N-oxide thereof.

  本发明涉及公式（I）的吡啶衍生物，作为mGlu5受体的拮抗剂。因此，这些化合物可能对治疗或预防通过拮抗mGlu5受体来治疗的疾病有用，其中Ar是苯基或萘基，可以被一个或多个C1-C4烷基，C1-C4烷氧基，C1-C5酰基，卤素，氨基，硝基，氰基，羟基，C1-C5酰基氨基，C1-C4烷基磺酰氨基，单，二或三氟代C1-C3烷基，取代基可以相同或不同，并且可能带有CONH2，CONHCH3，CON（CH3）2，CO2H，CO2CH3，OCF3，CH2NHCOCH3，CH2NH2，CH2N（CH3）2，CH2CN，CH2OH，CH2NHSO2CH3，CH2N（CH3）（CH2）2CN，CH2N（CH3）CH（CH3）2，CH2NHCH（CH3）2，CH2NH（CH2）2CH3，CH2NHCO2R4，CH2NHCH2CH3，CH2NHCH3NHCOC（CH3）2或N（S（O）2CH3）2取代基；R1是氢，卤素，R4，CN，C（NOH）R3，C（NO—R4）R3，（CH）2CO2R4，（CH2）nOR3，COR3，CF3，SR4，S（O）R4，S（O）2R4，COCH2CO2R3，NHSO2R4，NHCOR3，C（NOR3）NH2，CH2OCOR3，（CH2）nNH2，CON（CH3）2（CH2）nNHCO2R4，CO2R3，CONH2，CSNH2，C（NH）NHOR3，（CH2）nN（CH3）2或CONHNHCOR3；R2是1,2-乙烯基或1,2-乙炔基；R3是氢或C1-C4烷基；R4是C1-C4烷基；n为0、1、2、3或4；或其药学上可接受的盐或其N-氧化物。
• Pyridyl derivatives and their use as mGlu5 antagonists
  申请人：Eli Lilly and Company

  公开号：US07915424B2

  公开（公告）日：2011-03-29

  The present invention is directed toward pyridyl derivatives of formula (I) as antagonists of the mGlu5 receptor. As such the compounds may be useful for treatment or prevention of disorders remedied by antagonism of the mGlu5 receptor, wherein Ar is phenyl or napthyl each of which may be substituted by one or more C1-C4 alkyl, C1-C4 alkoxy, C1-C5 acyl, halo, amino, nitro, cyano, hydroxy, C1-C5 acylamino, C1-C4 alkylsulfonylamino, mono-, di- or trifluorinated C1-C3 alkyl, substituents which may be the same or different and may bear a CONH2, CONHCH3, CON(CH3)2, CO2H, CO2CH3, OCF3, CH2NHCOCH3, CH2NH2, CH2N(CH3)2, CH2CN, CH2OH, CH2NHSO2CH3, CH2N(CH3)(CH2)2 CN, CH2N(CH3)CH(CH3)2, CH2NHCH(CH3)2, CH2NH(CH2)2CH3, CH2NHCO2R4, CH2NHCH2CH3, CH2NHCH3 NHCOC(CH3)2, or N(S(O)2CH3)2 substituent; R1 is hydrogen, halo, R4, CN, C(NOH)R3, C(NO—R4)R3, (CH)2CO2R4, (CH2)n OR3, COR3, CF3, SR4, S(O)R4, S(O)2R4, COCH2CO2R3, NHSO2R4, NHCOR3, C(NOR3)NH2, CH2OCOR3, (CH2)nNH2, CON(CH3)2 (CH2)nNHCO2R4, CO2R3, CONH2, CSNH2, C(NH)NHOR3, (CH2)nN(CH3)2, or CONHNHCOR3; R2 is 1,2-ethenediyl or 1,2-ethynediyl; R3 is hydrogen or C1-C4 alkyl; R4 is C1-C4 alkyl; and n is 0, 1, 2, 3 or 4; or a pharmaceutically acceptable salt thereof, or an N-oxide thereof.

  本发明涉及公式（I）的吡啶衍生物作为mGlu5受体拮抗剂。因此，这些化合物可能有用于治疗或预防通过mGlu5受体拮抗疗法治疗的疾病，其中Ar为苯基或萘基，可以被一个或多个C1-C4烷基，C1-C4烷氧基，C1-C5酰基，卤素，氨基，硝基，氰基，羟基，C1-C5酰胺基，C1-C4烷基磺酰胺基，单，二或三氟化C1-C3烷基，取代基可以相同或不同，可以承载CONH2，CONHCH3，CON(CH3)2，CO2H，CO2CH3，OCF3，CH2NHCOCH3，CH2NH2，CH2N(CH3)2，CH2CN，CH2OH，CH2NHSO2CH3，CH2N(CH3)(CH2)2CN，CH2N(CH3)CH(CH3)2，CH2NHCH(CH3)2，CH2NH(CH2)2CH3，CH2NHCO2R4，CH2NHCH2CH3，CH2NHCH3，NHCOC(CH3)2或N（S（O）2CH3）2取代基；R1为氢，卤素，R4，CN，C（NOH）R3，C（NO—R4）R3，（CH）2CO2R4，（CH2）n OR3，COR3，CF3，SR4，S（O）R4，S（O）2R4，COCH2CO2R3，NHSO2R4，NHCOR3，C（NOR3）NH2，CH2OCOR3，（CH2）nNH2，CON（CH3）2（CH2）nNHCO2R4，CO2R3，CONH2，CSNH2，C（NH）NHOR3，（CH2）nN（CH3）2或CONHNHCOR3；R2为1,2-乙烯基或1,2-乙炔基；R3为氢或C1-C4烷基；R4为C1-C4烷基；n为0、1、2、3或4；或其药学上可接受的盐，或其N-氧化物。
• PYRIDYL DERIVATIVES AND THEIR USE AS MGLU5 RECEPTOR ANTAGONISTS
  申请人：Eli Lilly & Company

  公开号：EP1729771A1

  公开（公告）日：2006-12-13
• PHENYL-SUBSTITUTED NICOTINIC LIGANDS, AND METHODS OF USE THEREOF
  申请人：Georgetown University

  公开号：EP2776423B1

  公开（公告）日：2020-05-06