5-(4-甲氧基苯基)-3,6-二甲基-3,4-二氢-1H-吡啶-2-酮 | 89733-53-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 5-(4-甲氧基苯基)-3,6-二甲基-3,4-二氢-1H-吡啶-2-酮
• 英文名称: 3,6-Dimethyl-5-(4-methoxyphenyl)-2-oxo-1,2,3,4-tetrahydropyridine
• 英文别名: 3,4-dihydro-5-(4-methoxyphenyl)-3,6-dimethyl-2(1H)-pyridinone；3,6-dimethyl-5-(4-methoxyphenyl)-3,4-dihydro-2-pyridone；5-(4-Methoxyphenyl)-3,6-dimethyl-3,4-dihydropyridin-2(1H)-one；5-(4-methoxyphenyl)-3,6-dimethyl-3,4-dihydro-1H-pyridin-2-one
• CAS: 89733-53-9
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: IHMHSIAZMZWAFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(4-甲氧基苯基)-3,6-二甲基-3,4-二氢-1H-吡啶-2-酮 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 various solvent(s) 为溶剂， 反应 2.5h， 以92%的产率得到3,6-Dimethyl-5-(4-methoxyphenol)-2-oxo-1,2-dihydropyridine
  参考文献：
  名称：

  A Novel and Facile Two Step Synthesis of 5-Aryl-2(1H)-pyridones

  摘要：

  DOI：

  10.1055/s-1985-31189
• 作为产物：
  描述：

  对甲氧基苯基丙酮 、 甲基丙烯酰胺 在 potassium tert-butylate 作用下， 以 1,4-二氧六环 为溶剂， 以63%的产率得到5-(4-甲氧基苯基)-3,6-二甲基-3,4-二氢-1H-吡啶-2-酮
  参考文献：
  名称：

  A Novel and Facile Two Step Synthesis of 5-Aryl-2(1H)-pyridones

  摘要：

  DOI：

  10.1055/s-1985-31189

文献信息

• 2-Pyridinones and their use as cardiotonic agents
  申请人：Sterling Drug Inc.

  公开号：US04431651A1

  公开（公告）日：1984-02-14

  3,4-Dihydro-3-R.sub.1 -4-R.sub.2 -5-Q-6-R-2(1H)-pyridinones (I), where R.sub.1 and R.sub.2 are each hydrogen or methyl, R is lower-alkyl, and Q is 4(or 3)-hydroxyphenyl, 4(or 3)-methoxyphenyl, 4(or 3)-pyridinyl or 4(or 3)-pyridinyl having one or two lower-alkyl substituents, or acid-addition salts thereof, and their preparation are shown. Also shown is the cardiotonic use of I where Q is 4(or 3)-hydroxyphenyl, 4(or 3)-pyridinyl or 4(or 3)-pyridinyl having one or two lower-alkyl substituents.

  3,4-二氢-3-R.sub.1-4-R.sub.2-5-Q-6-R-2(1H)-吡啶酮(I)，其中R.sub.1和R.sub.2分别为氢或甲基，R为低碳烷基，Q为4(或3)-羟基苯基、4(或3)-甲氧基苯基、4(或3)-吡啶基或带有一个或两个低碳烷基取代基的4(或3)-吡啶基，或其酸盐，以及它们的制备。还显示了I的强心用途，其中Q为4(或3)-羟基苯基、4(或3)-吡啶基或带有一个或两个低碳烷基取代基的4(或3)-吡啶基。
• Tertiary 2,5-dialkyl-3-phenylpiperidine derivatives having
  申请人：Duphar International Research B.V.

  公开号：US05091393A1

  公开（公告）日：1992-02-25

  The invention relates to a group of tertiary 2,5-dialkyl-3-phenylpiperidine derivatives, having opiate-antagonistic activity represented by general formula 4, ##STR1## wherein A.sub.1 is hydrogen, an optionally esterified hydroxyl group or mercapto group, a group NHA.sub.8 or --CONHA.sub.8, wherein A.sub.8 is hydrogen, alkyl having 1-6 C-atoms or alkylcarbonyl having 2-7 C-atoms; A.sub.2 is hydrogen or, when A.sub.1 is hydrogen, one of the other meanings of A.sub.1, or A.sub.1 and A.sub.2 together with the 2 carbon atoms of the benzene ring,constitute a heterocyclic group which consists of five or six ring atoms and which comprises a group --NH-- and optionally as a second hetero atom may comprise an oxygen atom, sulphur atom or nitrogen atom; A.sub.3 and A.sub.4 independently of each other are straight or branched alkyl or alkenyl having 1-6 C-atoms; A.sub.5 is a straight or branched alkylene chain having 2-8 C-atoms; X is the carbonyl group or ketalized carbonyl group or the group>CHOH, --CONH--, --NHCO--, methylene, >CHC.sub.6 H.sub.5, or an oxygen atom or sulphur atom; A.sub.6 is an alkyl group, cycloalkyl group or cycloalkylalkyl group having at most 10 C-atoms and optionally substituted with one or more groups A.sub.7, or is a phenyl group or phenylalkyl group having 1-4 C-atoms in the alkyl group and optionally substituted with one or more groups A.sub.7, and A.sub.7 is alkyl, alkoxy or alkylthio having 1-4 C-atoms, amino, mono- or dialkylamino having 1-4 C-atoms per alkyl group, hydroxyalkyl, alkylcarbonyl, alkylaminocarbonyl or alkoxycarbonyl having 1-4 C-atoms in the alkyl group, nitro, cyano, halogen, trifluoromethyl, trifluoromethoxy, alkylsulphonyl having 1-4 C-atoms, or aminosulphonyl. These compounds have a pure opiate-antagonistic activity, i.e. without an agonistic activity component.

  本发明涉及一类三级2,5-二烷基-3-苯基哌啶衍生物，其具有通过通式4表示的阿片拮抗活性，其中A.sub.1是氢、一个可选酯化的羟基或巯基、一个NHA.sub.8或--CONHA.sub.8基团，其中A.sub.8是氢、具有1-6个碳原子的烷基或具有2-7个碳原子的烷基酰基；A.sub.2是氢或者当A.sub.1是氢时，A.sub.1的其他含义之一，或者A.sub.1和A.sub.2与苯环的2个碳原子一起构成一个由五个或六个环原子组成的杂环基团，其中包括一个--NH--基团，可选地，作为第二个杂原子，可以包括一个氧原子、硫原子或氮原子；A.sub.3和A.sub.4独立地是直链或支链烷基或烯基，具有1-6个碳原子；A.sub.5是具有2-8个碳原子的直链或支链烷基链；X是羰基或缩醛羰基或基团>CHOH、--CONH--、--NHCO--、亚甲基、>CHC.sub.6 H.sub.5、或氧原子或硫原子；A.sub.6是具有最多10个碳原子的烷基、环烷基或环烷基烷基，可选地取代一个或多个基团A.sub.7，或者是具有1-4个碳原子的烷基取代的苯基或苯基烷基，可选地取代一个或多个基团A.sub.7，A.sub.7是具有1-4个碳原子的烷基、烷氧基或烷硫基、氨基、1-4个碳原子的烷基组成的单烷基或双烷基氨基、羟基烷基、烷基羰基、烷基氨基羰基或烷氧基羰基，具有1-4个碳原子的硝基、氰基、卤素、三氟甲基、三氟甲氧基、具有1-4个碳原子的烷基磺酰基或氨基磺酰基。这些化合物具有纯阿片拮抗活性，即没有激动活性成分。
• 2(1H)-pyridinones and preparation, useful as cardiotonics
  申请人：STERLING DRUG INC.

  公开号：EP0109628A1

  公开（公告）日：1984-05-30

  3,4-Dihydro-3-R1-4-R2-5-Q-6-R-2 (1H)-pyridinones (I), where R1 and R2 are each hydrogen or methyl, R is lower-alkyl, and Q is 4 (or 3)-hydroxyphenyl, 4 (or 3)-methoxyphenyl, 4 (or 3)-pyridinyl or 4 (or 3)-pyridinyl having one or two lower-alkyl substituents, or acid-addition salts thereof, as well as the corresponding 3-R1-4-R2-5-Q-6-R-2 (1H)-pyridinones where at least one of R1 and R2 is methyl. The compounds have cardiotonic use when Q is 4 (or 3)-hydroxyphenyl, 4 (or 3)-pyridinyl or 4 (or 3)-pyridinyl having one or two lower-alkyl substituents. Said compounds are prepared from butanenitriles, butanoates, acrylamides or mixtures of alkanones and acetoacetamide, with optional conversion of the 3,4-dihydro compounds obtained to the 3,4-unsaturated compounds by heating with sulfur in an inert solvent and conversion of the methoxyphenyl compounds to the hydroxyphenyl compounds.

  3,4-二氢-3-R1-4-R2-5-Q-6-R-2 (1H)-吡啶酮 (I)，其中 R1 和 R2 分别为氢或甲基，R 为低级烷基，Q 为 4（或 3）-羟基苯基、4（或 3）-甲氧基苯基、4（或 3）-吡啶基或具有一个或两个低级烷基取代基的 4（或 3）-吡啶基，或其酸加成盐、4（或 3）-吡啶基或具有一个或两个低级烷基取代基的 4（或 3）-吡啶基，或其酸加成盐，以及相应的 3-R1-4-R2-5-Q-6-R-2 (1H)-pyridinones （其中 R1 和 R2 中至少有一个是甲基）。当 Q 为 4（或 3）-羟基苯基、4（或 3）-吡啶基或具有一个或两个低级烷基取代基的 4（或 3）-吡啶基时，这些化合物具有强心作用。上述化合物由丁烯腈、丁酸盐、丙烯酰胺或烷酮和乙酰乙酰胺的混合物制备，可选择在惰性溶剂中用硫加热，将得到的 3，4-二氢化物转化为 3，4-不饱和化合物，并将甲氧基苯基化合物转化为羟基苯基化合物。
• Tertiary 2,5-dialkyl-3-phenyl-piperidine derivatives having opiate-antagonistic activity
  申请人：DUPHAR INTERNATIONAL RESEARCH B.V

  公开号：EP0299549A2

  公开（公告）日：1989-01-18

  The invention relates to a group of tertiary 2,5-dialkyl-3-phenylpiperidine derivatives, having opiate-antagonistic activity represented by general formula 4, wherein S1 is hydrogen, an optionally esterified hydroxyl group or mercapto group, a group -NHS8 or -CONHS8, wherein S8 is hydrogen, alkyl having 1-6 C-atoms or alkylcarbonyl having 2-7 C-atoms; S2 is hydrogen or, when S1 is hydrogen, one of the other meanings of Si, or S1 and S2 together with the 2 carbon atoms of the benzene ring, constitute a heterocyclic group which consists of five or six ring atoms and which comprises a group -NH-and optionally as a second hetero atom may comprise an oxygen atom, sulphur atom or nitrogen atom; S3 and S4 independently of each other are straight or branched alkyl or alkenyl having 1-6 C-atoms; Ss is a straight or branched alkylene chain having 2-8 C-atoms; X is the carbonyl group or ketalised carbonyl group or the group CHOH, -CONH-, -NHCO-, methylene, CHC6H5 or an oxygen atom or sulphur atom; S6 is an alkyl group, cycloalkyl group or cycloalkylalkyl group having at most 10 C-atoms and optionally substituted with one or more groups 87, or is a phenyl group or phenylalkyl group having 1-4 C-atoms in the alkyl group and optionally substituted with one or more groups S7. and S7 is alkyl, alkoxy or alkylthio having 1-4 C-atoms, amino, mono- or dialkylamino having 1-4 C-atoms per alkyl group, hydroxyalkyl, alkylcarbonyl , alkylaminocarbonyl or alkoxycarbonyl having 1-4 C-atoms in the alkyl group, nitro, cyano, halogen, trifluoromethyl, trifluoromethoxy, alkylsulphonyl having 1-4 C-atoms, or aminosuiphonyl. These compounds have a pure opiate-antagonistic activity, i.e. without an agonistic activity component.

  本发明涉及一组具有鸦片拮抗剂活性的 2,5-二烷基-3-苯基哌啶叔衍生物，由通式 4 表示、 其中 S1 是氢、任选酯化的羟基或巯基、基团 -NHS8 或 -CONHS8，其中 S8 是氢、具有 1-6 个 C 原子的烷基或具有 2-7 个 C 原子的烷基羰基； S2 是氢，或当 S1 是氢时，是 Si 的其他含义之一，或 S1 和 S2 与苯环上的 2 个碳原子一起构成一个杂环基团，该杂环基团由 5 个或 6 个环原子组成，其中包含一个基团-NH，作为第二个杂原子可选择包含一个氧原子、硫原子或氮原子； S3 和 S4 相互独立地为具有 1-6 个 C 原子的直链或支链烷基或烯基； Ss 是具有 2-8 个 C 原子的直链或支链亚烷基； X 是羰基或酮化羰基或 CHOH、-CONH-、-NHCO-、亚甲基、CHC6H5 或氧原子或硫原子； S6 是最多具有 10 个 C 原子并可选择被一个或多个基团 87 取代的烷基、环烷基或环烷基烷基，或 是烷基中具有 1-4 个 C 原子并可选择被一个或多个基团 S7 取代的苯基或苯基烷基。 S7 是烷基、烷氧基或具有 1-4 个 C 原子的烷硫基、氨基、每个烷基具有 1-4 个 C 原子的单烷基或二烷基氨基、羟基烷基、烷基羰基、烷基氨基羰基或烷氧基羰基、硝基、氰基、卤素、三氟甲基、三氟甲氧基、具有 1-4 个 C 原子的烷基磺酰基或氨基水杨基。 这些化合物具有纯粹的阿片拮抗活性，即不含激动活性成分。
• SINGH, B., SYNTHESIS, BRD, 1985, N 3, 305-306
  作者：SINGH, B.

  DOI：——

  日期：——