4-methoxy-3-nitrophenylacetone | 90617-47-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-methoxy-3-nitrophenylacetone
• 英文别名: 3-(4-methoxy-3-nitrophenyl)propan-2-one；1-(4-methoxy-3-nitrophenyl)propan-2-one
• CAS: 90617-47-3
• 化学式: C₁₀H₁₁NO₄
• 分子量: 209.202
• InChiKey: XQSCNHIENAVBQO-UHFFFAOYSA-N

物化性质

• 沸点：
  356.1±27.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methoxy-3-nitrophenylacetone 在 钯 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以gave desired product 11 (2.41 g, 94%)的产率得到3-Amino-4-methoxyphenylacetone
  参考文献：
  名称：

  5H-2,3-benzodiazepine antagonists of excitatory amino acid receptors

  摘要：

  提供了代替苯二氮平的化合物组合物，其作为非NMDA离子型兴奋性氨基酸（EAA）受体拮抗剂具有活性。这些化合物通常是7-或8-单取代的5H-2,3-苯二氮平。这些组合物可用于治疗与非NMDA亚型离子型EAA受体过度激活有关的疾病。这些化合物还可用作测试试剂，以识别和表征其他治疗这些疾病的化合物。这些化合物在治疗上可用作镇静剂或用于治疗神经精神药理学疾病，例如中风、缺血和癫痫。这些组合物可以与适当的载体结合，用于口服或静脉注射。这些化合物可以口服或静脉注射，用于治疗与非NMDA EEA受体功能有关的各种疾病。

  公开号：

  US20020025958A1
• 作为产物：
  描述：

  对甲氧基苯基丙酮 在 硝酸 作用下， 以 (2S)-N-methyl-1-phenylpropan-2-amine hydrate 、 乙酸酐 为溶剂， 以59%的产率得到4-methoxy-3-nitrophenylacetone
  参考文献：
  名称：

  5H-2,3-benzodiazepine antagonists of excitatory amino acid receptors

  摘要：

  提供了替代苯二氮平类化合物，其作为非NMDA离子型兴奋性氨基酸（EAA）受体拮抗剂具有活性。这些化合物通常是7-或8-单取代的5H-2,3-苯二氮平。这些化合物可用于治疗与非NMDA离子型EAA受体过度激活相关的疾病。此外，这些化合物还可用作测试剂，以识别和表征其他化合物用于治疗这些疾病。这些化合物在治疗上可用作镇静剂或用于治疗神经精神药理学疾病，如中风、缺血和癫痫。这些化合物可以与适当的载体组合用于口服或静脉注射。这些化合物可以口服或静脉注射用于治疗与非NMDA EEA受体功能相关的各种疾病。

  公开号：

  US20020025958A1

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-(hydroxy- and/or
  申请人：Sterling Drug Inc.

  公开号：US04515797A1

  公开（公告）日：1985-05-07

  1-R.sub.1 -3-amino-5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinones or salts thereof, which are useful as cardiotonics, where R.sub.1 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 at least one of R' and R" being other than hydrogen 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 is shown, the latter including cardiotonically active novel 1-R.sub.1 -1,2-dihydro-5-(3-R.sub.2 -4-R.sub.3 -phenyl)-6-R-nicotinonitriles where R.sub.1 and R are defined as above, and R.sub.2 and R.sub.3 have the above given definitions for R' and R" or where R.sub.2 is nitro and R.sub.3 is hydroxy. Also shown are cardiotonic compositions and cardiotonic method of use of above-said compounds.

  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。
• 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。
• Process for producing phenylacetones
  申请人：UBE INDUSTRIES, LTD.

  公开号：EP0101223A2

  公开（公告）日：1984-02-22

  A phenylacetone or its derivative having the general formula (I): wherein X. Y, and Z are independently a hydrogen atom, a hydroxyl group, a halogen atom, a nitro group, an amino group, a lower alkyl group having 1 to 6 carbon atoms, a lower alkoxy group having 1 to 6 carbon atoms, or a benzyloxy group and any two substituents of X, Y, and Z may form, together with the benzene ring, a heterocycling ring having 5 to 7 members including 1 or 2 oxygen atoms is produced at a high yield and a high selectivity by reacting a 3-phenylpropylene or its derivative having the general formula (II): wherein X, Y and Z are as defined above, with an alkyl nitrite having the general formula (III):wherein R is an aliphatic, aromatic or alicyclic saturated or unsaturated hydrocarbon group in the presence of (a) water, (b) an alcohol, (c) a palladium catalyst, and (d) an optional amine or copper compound, or by reacting the above-mentioned 3-phenylpropylene or its derivative with the above-mentioned alkyl nitrite in the presence of (a) an alcohol, (b) a palladium catalyst and (c) an optional amine or copper compound to form 1-phemrl-2,2-dialkoxypropane or it derivative having the general formula (IV): wherein X, Y, Z and R are as defined above, followed by hydrolyzing the reaction product.

  具有通式(I)的苯丙酮或其衍生物： 其中 X.Y和Z独立地为氢原子、羟基、卤素原子、硝基、氨基、1至6个碳原子的低级烷基、1至6个碳原子的低级烷氧基或苄氧基，且X、Y和Z的任意两个取代基可与苯环一起形成一个具有5至7个成员（包括1或2个氧原子）的杂环： 其中 X、Y 和 Z 如上定义，与通式（III）的亚硝酸烷基酯反应：其中 R 为脂肪族、芳香族或脂环族饱和或不饱和烃基，在 (a) 水、(b) 醇、(c) 钯催化剂和 (d) 任选胺或铜化合物存在下反应、或在(a)醇、(b)钯催化剂和(c)任选胺或铜化合物存在下，使上述 3-苯基丙烯或其衍生物与上述亚硝酸烷基酯反应，生成通式为(IV)的 1-苯基-2,2-二烷氧基丙烷或其衍生物： 其中 X、Y、Z 和 R 如上定义，然后水解反应产物。
• 5H-2,3-BENZODIAZEPINE ANTAGONISTS OF EXCITATORY AMINO ACID RECEPTORS
  申请人：Annovis, Inc.

  公开号：EP1296960A2

  公开（公告）日：2003-04-02