1,2-dihydro-5-(4-methoxyphenyl)-2-oxonicotinonitrile | 84462-77-1

• 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: 1,2-dihydro-5-(4-methoxyphenyl)-2-oxonicotinonitrile
• 英文别名: 5-(4-Methoxyphenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile；5-(4-methoxyphenyl)-2-oxo-1H-pyridine-3-carbonitrile
• CAS: 84462-77-1
• 化学式: C₁₃H₁₀N₂O₂
• 分子量: 226.235
• InChiKey: NDTOGYXXBVSCRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2-dihydro-5-(4-methoxyphenyl)-2-oxonicotinonitrile 在 lithium iodide 作用下， 以 2,3,5-三甲基吡啶 为溶剂， 生成 1,2-dihydro-5-(4-hydroxyphenyl)-2-oxonicotinonitrile
  参考文献：
  名称：

  3-Amino-5-(hydroxy- and/or

  摘要：

  1-R.sub.1 -3-氨基-5-(3-R'-4-R"-苯基)-6-R-2(1H)-吡啶酮或其盐，可用作心脏强心剂，其中R.sub.1是氢、低烷基或低羟基烷基，R是氢或低烷基，R'和R"分别是氢、羟基或氨基，其中R'或R"至少有一个不是氢，通过将相应的3-氨基甲酰化合物与能够将氨基甲酰转化为氨基的试剂反应制备，或者首先将R'和R"分别是氢、硝基或低烷氧基，其中R'和R"中至少有一个不是氢的相应的3-氨基甲酰化合物与能够将氨基甲酰转化为氨基的试剂反应，然后将所得的3-氨基化合物与能够将低烷氧基转化为羟基和/或能够将硝基转化为氨基的试剂反应，其中R'和/或R"是低烷氧基和/或硝基。显示了相应的3-氨基甲酰和3-氰基化合物的制备，后者包括具有心脏强心活性的新颖的1-R.sub.1 -1,2-二氢-5-(3-R.sub.2 -4-R.sub.3 -苯基)-6-R-烟酰腈，其中R.sub.1和R如上所定义，R.sub.2和R.sub.3具有上述给定的R'和R"的定义，或者其中R.sub.2是硝基，R.sub.3是羟基。还显示了心脏强心剂组合物和上述化合物的心脏强心方法的用途。

  公开号：

  US04515797A1
• 作为产物：
  描述：

  3-(dimethylamino)-2-(4-methoxyphenyl)prop-2-enal 、 氰乙酰胺 生成 1,2-dihydro-5-(4-methoxyphenyl)-2-oxonicotinonitrile
  参考文献：
  名称：

  LESHER, G. Y.;OPALKA, CH. J. ,, JR.;PAGE, D. F.

  摘要：

  DOI：

文献信息

• 5-(Hydroxy- and/or amino-phenyl)-6-(lower-alkyl)-2-(1H)-pyridinones,
  申请人：Sterling Drug Inc.

  公开号：US04465686A1

  公开（公告）日：1984-08-14

  Disclosed and claimed is the cardiotonic use of 1-R.sub.1 -5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinones (II), where R.sub.1 is hydrogen, lower-alkyl or lower-hydroxyalkyl, R is lower-alkyl or hydrogen, and, R' and R" are each hydrogen, amino or hydroxy, at least one of R' or R" being other than hydrogen, or where R' is nitro when R" is hydroxy, or pharmaceutically acceptable acid-addition salts thereof where at least one of R' and R" is amino. Also disclosed and claimed are 1-R.sub.1 -5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinones (I), where R.sub.1, R' and R" are defined as above and R is lower-alkyl and acid-addition salts thereof where at least one of R' and R" is amino. Also shown and claimed is the process which comprises reacting 1-R.sub.1 -1,2-dihydro-2-oxo-5-(3-R'-4-R"-phenyl)-6-R-nicotinonitrile, where R.sub.1 and R are defined as above for II, R' is hydrogen, hydroxy, methoxy or amino and R" is hydroxy, methoxy or hydrogen, preferably at least one of R' and R" being methoxy, or where R' is nitro and R" is hydrogen or methoxy, preferably methoxy, with 85% phosphoric acid to produce 1-R.sub.1 -5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinone.

  揭示和声明了1-R.sub.1 -5-(3-R'-4-R"-苯基)-6-R-2(1H)-吡啶酮（II）的强心作用，其中R.sub.1为氢、低烷基或低羟基烷基，R为低烷基或氢，R'和R"分别为氢、氨基或羟基，其中至少有一个R'或R"不是氢，或者当R"为羟基时，R'为硝基，或其药学上可接受的酸加合物盐，其中至少一个R'和R"为氨基。还揭示和声明了1-R.sub.1 -5-(3-R'-4-R"-苯基)-6-R-2(1H)-吡啶酮（I），其中R.sub.1、R'和R"的定义如上所述，R为低烷基，以及其药学上可接受的酸加合物盐，其中至少一个R'和R"为氨基。还显示和声明了一种过程，包括将1-R.sub.1 -1,2-二氢-2-氧代-5-(3-R'-4-R"-苯基)-6-R-烟酸腈与85%磷酸反应，其中R.sub.1和R的定义如上所述用于II，R'为氢、羟基、甲氧基或氨基，R"为羟基、甲氧基或氢，最好是R'和R"中至少一个为甲氧基，或者当R'为硝基且R"为氢或甲氧基时，最好为甲氧基，以产生1-R.sub.1 -5-(3-R'-4-R"-苯基)-6-R-2(1H)-吡啶酮。
• 3-Amino-5-(substituted)-2 (1H) pyridinones and 3-cyano compounds useful as cardiotonics and preparation thereof
  申请人：STERLING DRUG INC.

  公开号：EP0061774A2

  公开（公告）日：1982-10-06

  1-R1-3-amino-5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridi- nones or salts thereof, which are useful as cardiotonics, where R, is hydrogen, lower-alkyl, or lower-hydroxyalkyl, R is hydrogen or lower-alkyl, and, R' and R" are each hydrogen, hydroxy or amino at least one of R' or R" being other than hydrogen, are prepared by reacting the corresponding 3-carbamyl compound with a reagent capable of converting carbamyl to amino or by first reacting the corresponding 3-carbamyl compound where R' and R" are each hydrogen, nitro or lower-alkoxy with a reagent capable of converting carbamyl to amino and then reacting the resulting 3-amino compound where R' and/or R" are/is lower-alkoxy and/or nitro with a reagent capable of converting lower-alkoxy to hydroxy and/or with a reagent capable of converting nitro to amino. Preparation of the corresponding 3-carbamyl and 3-cyano compounds are described. The invention also concerns the 3- and/or 4-methoxy intermediates and certain novel 3-cyano analogs. Cyano compounds are also useful as cardiotonics.

  1-R1-3-氨基-5-(3-R'-4-R"-苯基)-6-R-2(1H)-吡啶-壬烷或其盐，可用作强心剂，其中 R 是氢、低级烷基或低级羟基烷基，R 是氢或低级烷基，R'和 R "各自是氢、羟基或氨基，R'或 R "中至少有一个不是氢、将相应的 3-氨基甲酰基化合物与能将氨基甲酰基转化为氨基的试剂反应，或先将 R' 和 R "均为氢、硝基或低级烷氧基的相应 3-氨基甲酰基化合物与能将氨基甲酰基转化为氨基的试剂反应，然后将所得 R' 和/或 R "为/或低级烷氧基和/或硝基的 3-氨基化合物与能将低级烷氧基转化为羟基的试剂和/或能将硝基转化为氨基的试剂反应，制备 3-氨基甲酰基化合物。本发明描述了相应的 3-氨基甲酰基和 3-氰基化合物的制备方法。本发明还涉及 3-和/或 4-甲氧基中间体和某些新型 3-氰基类似物。氰基化合物还可用作强心剂。
• 2(1H)-pyridinones and preparation thereof
  申请人：STERLING DRUG INC.

  公开号：EP0074091A2

  公开（公告）日：1983-03-16

  Novel 1-R,-3-Q-5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinones where R, is hydrogen, lower-alkyl or lower-hydroxyalkyl, R is lower-alkyl and, R' and R" are each hydrogen, amino or hydroxy, at least one of R' or R" being other than hydrogen, or R is nitro and R" is hydroxy, are useful as cardiotonics. Also known compounds where R is hydrogen are useful as cardiotonics. Both novel and known compounds can be prepared by a novel process which comprises reacting 1-RI-1,2-dihydro-2-oxo-5-(3-R'-4-R"- phenyl)-6-R-nicotinonitrile, where R1 and R are defined as above, R' is hydrogen, hydroxy, methoxy or amino and R" is hydrogen, hydroxy, amino or methoxy, at least one of R' and R" being other than hydrogen, or R' is nitro and R" is hydroxy with 85% phosphoric acid.

  新型 1-R,-3-Q-5-(3-R'-4-R"-苯基)-6-R-2(1H)-吡啶酮，其中 R 是氢、低级烷基或低级羟基烷基，R 是低级烷基，R'和 R "各自是氢、氨基或羟基，R'或 R "中至少有一个不是氢，或 R 是硝基，R "是羟基，可用作强心剂。此外，R 为氢的已知化合物也可用作强心剂。新型和已知化合物均可通过一种新型工艺制备，该工艺包括将 1-RI-1,2-二氢-2-氧代-5-(3-R'-4-R"-苯基)-6-R-烟腈（其中 R1 和 R 定义如上，R'为氢、羟基、甲氧基或氨基，R "为氢、羟基、氨基或甲氧基，R'和 R "中至少有一个不是氢，或 R'为硝基，R "为羟基）与 85%的磷酸反应。
• LESHER, G. Y.;OPALKA, C. J. ,, JR.;PAGE, D. F.
  作者：LESHER, G. Y.、OPALKA, C. J. ,, JR.、PAGE, D. F.

  DOI：——

  日期：——
• LESHER, G. Y.;OPALKA, CH. J. ,, JR.;PAGE, D. F.
  作者：LESHER, G. Y.、OPALKA, CH. J. ,, JR.、PAGE, D. F.

  DOI：——

  日期：——