3-氯-5-乙炔基吡啶 | 329202-22-4

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 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: 3-氯-5-乙炔基吡啶
• 中文别名: 3-氯-5-乙炔吡啶
• 英文名称: 3-Chloro-5-ethynylpyridine
• 英文别名: 3-Chloro-5ethynylpyridine
• CAS: 329202-22-4
• 化学式: C₇H₄ClN
• mdl: MFCD09832884
• 分子量: 137.568
• InChiKey: MZOIQYPOUQWDQZ-UHFFFAOYSA-N

物化性质

• 沸点：
  207.5±25.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  3-氯-5-乙炔基吡啶 在 Oxone 、 四丁基溴化铵 作用下， 以 水 、 乙腈 为溶剂， 以50 %的产率得到5-氯烟酸
  参考文献：
  名称：

  芳基乙炔常温电氧化合成芳基羧酸

  摘要：

  证明了通过芳基乙炔的环境电氧化有效且环境友好地合成芳基羧酸。在乙腈和水的混合溶液中，以过一硫酸钾（Oxone）为添加剂，反应在一定的外加电位下顺利进行。目标产物的分离收率高达90%，并且反应表现出优异的官能团耐受性。在该电化学系统中，不需要过渡金属催化剂、额外的酸/碱和高温。该方法可能开辟一条通过电化学策略合成羧酸的途径。

  DOI：

  10.1055/s-0041-1738456
• 作为产物：
  描述：

  3-氯-5-[(三甲基甲硅烷基)乙炔基]吡啶 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以52%的产率得到3-氯-5-乙炔基吡啶
  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

文献信息

• [EN] PYRIDYL DERIVATIVES AND THEIR USE AS MGLU5 RECEPTOR ANTAGONISTS<br/>[FR] DERIVES DE PYRIDYLE ET LEUR UTILISATION EN TANT QU'ANTAGONISTES DU RECEPTEUR DE MGLU5
  申请人：LILLY CO ELI

  公开号：WO2005094822A1

  公开（公告）日：2005-10-13

  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)n NH2, 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。
• Imidazolyl and pyrazolyl ethyne compounds
  申请人：Cosford D. Nicholas

  公开号：US20050085523A1

  公开（公告）日：2005-04-21

  In accordance with the present invention, there is provided a novel class of heterocyclic compounds. Compounds of the invention contain a substituted, unsaturated five, six or seven membered heterocyclic ring that includes at least one nitrogen atom and at least one carbon atom. The ring additionally includes three, four or five atoms independently selected from carbon, nitrogen, sulfur and oxygen atoms. The heterocyclic ring has at least one substituent located at a ring position adjacent to a ring nitrogen atom. This mandatory substituent of the ring includes a moiety (B), linked to the heterocyclic ring via a carbon-carbon double bond, a carbon-carbon triple bond or an azo group. The mandatory substituent is positioned adjacent to the ring nitrogen atom. Invention compounds are capable of a wide variety of uses. For example heterocyclic compounds can act to modulate physiological processes by functioning as agonists and antagonists of receptors in the nervous system. Invention compounds may also act as insecticides, and as fungicides. Pharmaceutical compositions containing invention compounds also have wide utility.

  根据本发明，提供了一类新型的杂环化合物。该发明的化合物包含一个取代的、不饱和的五、六或七元杂环环，其中至少包含一个氮原子和至少一个碳原子。该环另外包括三、四或五个独立选择的碳、氮、硫和氧原子。杂环环在至少一个邻近环氮原子的环位置上具有至少一个取代基。该环的强制性取代基包括一个通过碳-碳双键、碳-碳三键或偶氮基与杂环环相连的基团（B）。强制性取代基位于环氮原子的邻近位置。本发明的化合物能够具有各种用途。例如，杂环化合物可以通过作为神经系统受体的激动剂和拮抗剂来调节生理过程。本发明的化合物也可以作为杀虫剂和杀菌剂。含有本发明化合物的药物组合物也具有广泛的用途。
• Thiazolyl(pyridyl)ethyne compounds
  申请人：Merck & Co., Inc.

  公开号：US06774138B2

  公开（公告）日：2004-08-10

  In accordance with the present invention, there is provided a novel class of heterocyclic compounds. Compounds of the invention contain a substituted, unsaturated five, six or seven membered heterocyclic ring that includes at least one nitrogen atom and at least one carbon atom. The ring additionally includes three, four or five atoms independently selected from carbon, nitrogen, sulfur and oxygen atoms. The heterocyclic ring has at least one substituent located at a ring position adjacent to a ring nitrogen atom. This mandatory substituent of the ring includes a moiety (B), linked to the heterocyclic ring via a carbon-carbon double bond, a carbon-carbon triple bond or an azo group. The mandatory substituent is positioned adjacent to the ring nitrogen atom. Invention compounds are capable of a wide variety of uses. For example heterocyclic compounds can act to modulate physiological processes by functioning as agonists and antagonists of receptors in the nervous system. Invention compounds may also act as insecticides, and as fungicides. Pharmaceutical compositions containing invention compounds also have wide utility.

  根据本发明，提供了一类新型的杂环化合物。该发明的化合物包含一个取代的、不饱和的五、六或七元杂环环，其中至少包含一个氮原子和至少一个碳原子。该环另外包括三、四或五个独立选择的碳、氮、硫和氧原子。杂环环至少有一个取代基位于邻近环氮原子的环位置。该环的强制性取代基包括一个通过碳-碳双键、碳-碳三键或偶氮基与杂环环连接的基团（B）。强制性取代基位于环氮原子的邻近位置。发明的化合物能够具有各种用途。例如，杂环化合物可以通过作为神经系统受体的激动剂和拮抗剂来调节生理过程。发明的化合物也可以作为杀虫剂和杀菌剂。含有发明化合物的药物组合物也具有广泛的用途。
• [EN] NOVEL AMINOPYRIDINE DERIVATIVES AS mGIuR5 ANTAGONISTS<br/>[FR] DERIVES NOUVEAUX D'AMINOPYRIDINE UTILES COMME ANTAGONISTES DE MGLUR5
  申请人：ADDEX PHARMACEUTICALS SA

  公开号：WO2004078728A1

  公开（公告）日：2004-09-16

  The invention relates to novel aminopyridine derivatives of formula (I) wherein R1 is methyl an R4 and amino group NR6R7 and R5 forms an arylalkynyl- or heteroarylalkynyl-group. The compounds are useful in the prevention or treatment of central nervous system disorders as well as other disorders modulated by mGIuR5 receptors.

  这项发明涉及式（I）的新型氨基吡啶衍生物，其中R1为甲基，R4和氨基NR6R7，R5形成芳基炔基或杂芳基炔基。这些化合物在预防或治疗中枢神经系统疾病以及其他受mGIuR5受体调节的疾病方面具有用途。
• PHENYL OR PYRIDINYL-ETHYNYL DERIVATIVES
  申请人：Jaeschke Georg

  公开号：US20120270852A1

  公开（公告）日：2012-10-25

  The present invention relates to ethynyl derivatives of formula I wherein Y is N or C—R 3 ; R 3 is hydrogen, methyl, halogen or nitrile; R 1 is phenyl or pyridinyl, each of which is optionally substituted by halogen, lower alkyl or lower alkoxy; R 2 /R 2′ are each independently hydrogen, lower alkyl or lower alkyl substituted by halogen, or R 2 and R 2′ together with the N-atom to which they are attached form a morpholine ring, a piperidine ring or an azetidine ring, each of which is unsubstituted or substituted one or more substituents selected from lower alkoxy, halogen, hydroxy and methyl; R 4 /R 4′ are each independently hydrogen or lower alkyl, or R 4 and R 4′ together form a C 3-5 cycloalkyl-, tetrahydrofuran- or an oxetane-ring; or to a pharmaceutically acceptable acid addition salt, to a racemic mixture, or to its corresponding enantiomer and/or optical isomer and/or stereoisomer thereof. Compounds of formula I are positive allosteric modulators (PAM) of the metabotropic glutamate receptor subtype 5 (mGluR5).

  本发明涉及公式I的乙炔衍生物，其中Y为N或C—R3；R3为氢、甲基、卤素或腈基；R1为苯基或吡啶基，每个基团可选择地被卤素、低烷基或低烷氧基取代；R2/R2′各自独立地为氢、低烷基或被卤素取代的低烷基，或者R2和R2′与它们连接的N原子一起形成一个吗啉环、哌啶环或氮杂环，每个环未取代或取代一个或多个从低烷氧基、卤素、羟基和甲基中选取的取代基；R4/R4′各自独立地为氢或低烷基，或者R4和R4′一起形成一个C3-5环烷基、四氢呋喃环或噁唑环；或者形成药用可接受的酸盐、对映体混合物，或其对应的对映体和/或光学异构体和/或立体异构体。公式I的化合物是代谢型谷氨酸受体亚型5（mGluR5）的正向变构调节子（PAM）。