3-amino-1-(4-nitrophenyl)-2-buten-1-one | 102252-95-9

• 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: 3-amino-1-(4-nitrophenyl)-2-buten-1-one
• 英文别名: 3-(4-Nitrophenyl)-1-methyl-3-oxo-1-propenamine；3-amino-1-(4-nitrophenyl)but-2-en-1-one
• CAS: 102252-95-9
• 化学式: C₁₀H₁₀N₂O₃
• 分子量: 206.201
• InChiKey: HRHPQDLRRMZGNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  88.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-amino-1-(4-nitrophenyl)-2-buten-1-one 在 platinum(IV) oxide ammonium acetate 、 氢气 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 5-(4-aminophenyl)-1,6-naphthyridin-2(1H)-one
  参考文献：
  名称：

  Novel cAMP PDE III inhibitors: 1,6-naphthyridin-2(1H)-ones

  摘要：

  Two series of medorinone (3) analogs were prepared by modifications at C(2) and C(5). The C(2)-series was prepared from 2-chloro-5-methyl-1,6-naphthyridine (4) by replacement of the chloro group with various nucleophiles. The C(5)-series was prepared from 5-acyl-6-[2-(dimethylamino)ethenyl]-2-(1H)-pyridinone (11), 5-bromo-1,6-naphthyridin-2(1H)-one (17), and 1,3-diketones 19 and 27. 1,6-Naphthyridin-2(1H)-ones are novel inhibitors of cAMP PDE III. Modification of the carbonyl group of 3 or N-methylation at N(1) resulted in a dramatic loss of enzyme activity. Absence of the C(5)-methyl group of medorinone (3) or its shift to C(3) or C(7) also resulted in reduced activity. Substitution at C(3) also diminished activity. However, substitution at C(5) by a wide variety of substituents led to improvement of enzyme activity and several C(5)-substituted analogs were more potent than milrinone.

  DOI：

  10.1021/jm00104a012
• 作为产物：
  描述：

  1-(4-硝基苯基)丁烷-1,3-二酮 在 ammonium acetate 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以80%的产率得到3-amino-1-(4-nitrophenyl)-2-buten-1-one
  参考文献：
  名称：

  Novel cAMP PDE III inhibitors: 1,6-naphthyridin-2(1H)-ones

  摘要：

  Two series of medorinone (3) analogs were prepared by modifications at C(2) and C(5). The C(2)-series was prepared from 2-chloro-5-methyl-1,6-naphthyridine (4) by replacement of the chloro group with various nucleophiles. The C(5)-series was prepared from 5-acyl-6-[2-(dimethylamino)ethenyl]-2-(1H)-pyridinone (11), 5-bromo-1,6-naphthyridin-2(1H)-one (17), and 1,3-diketones 19 and 27. 1,6-Naphthyridin-2(1H)-ones are novel inhibitors of cAMP PDE III. Modification of the carbonyl group of 3 or N-methylation at N(1) resulted in a dramatic loss of enzyme activity. Absence of the C(5)-methyl group of medorinone (3) or its shift to C(3) or C(7) also resulted in reduced activity. Substitution at C(3) also diminished activity. However, substitution at C(5) by a wide variety of substituents led to improvement of enzyme activity and several C(5)-substituted analogs were more potent than milrinone.

  DOI：

  10.1021/jm00104a012

文献信息

• 5-(Phenyl)-1,6-naphthyridin-2(1H)-ones, their cardiotonic use and
  申请人：Sterling Drug Inc.

  公开号：US04560691A1

  公开（公告）日：1985-12-24

  1-R-5-Ar-1,6-naphthyridin-2(1H)-ones (I) or salts thereof, where R is hydrogen or methyl, and Ar is phenyl or phenyl substituted by methyl, ethyl, methoxy, ethoxy, hydroxy, amino, acetylamino, methanesulfonylamino, bromo, chloro, fluoro, cyano or carbamyl are useful as cardiotonic agents and corresponding compounds where Ar is nitrophenyl are useful as intermediates. Also shown as intermediates, are 5-(Ar--CO)-6-[2-(di-lower-alkylamino)-ethenyl]-2(1H)-pyridinones (II) or salts thereof, where Ar is phenyl or phenyl substituted by methyl, ethyl, methoxy, ethoxy, bromo, chloro, fluoro, cyano or nitro and 5-(Ar--CO)-6-methyl-2(1H)-pyridinones (III) where Ar is phenyl or phenyl substituted by methyl, ethyl, methoxy, ethoxy, bromo, chloro, fluoro, hydroxy, cyano or nitro; said compounds (III) where Ar is phenyl or hydroxyphenyl also are useful as cardiotonic agents. Processes for preparing the compounds of formulas I, II and III are shown.

  1-R-5-Ar-1,6-萘啶并[2(1H)-酮]（I）或其盐，其中R为氢或甲基，Ar为苯基或被甲基、乙基、甲氧基、乙氧基、羟基、氨基、乙酰氨基、甲磺酰氨基、溴、氯、氟、氰或氨基甲酰基取代的苯基，可用作心力增强剂，其中Ar为硝基苯基的相应化合物可用作中间体。还显示了5-(Ar-CO)-6-[2-(二低烷基氨基)-乙烯基]-2(1H)-吡啶酮（II）或其盐，其中Ar为苯基或被甲基、乙基、甲氧基、乙氧基、溴、氯、氟、氰或硝基取代的苯基，以及5-(Ar-CO)-6-甲基-2(1H)-吡啶酮（III），其中Ar为苯基或被甲基、乙基、甲氧基、乙氧基、溴、氯、氟、羟基、氰或硝基取代的苯基；其中Ar为苯基或羟基苯基的化合物（III）也可用作心力增强剂。显示了制备公式I、II和III化合物的过程。
• Rongalite as C1 Synthon in the Synthesis of Divergent Pyridines and Quinolines
  作者：Huan Gao、Liyun Zhou、Jie-Ping Wan、Yunyun Liu

  DOI：10.1021/acs.joc.3c00428

  日期：2023.6.2

  Rongalite has been used as a cheap and efficient carbon synthon for the synthesis of divergent N-heteroaromatics, including different pyridines and quinolines. The selective synthesis of different products can be achieved by employing enaminones or enaminones/anilines as reaction partners. In addition, compared with the reaction using conventional aldehyde synthons, rongalite displays an evident advantage

  Rongalite 已被用作一种廉价且高效的碳合成子，用于合成不同的 N-杂芳烃，包括不同的吡啶和喹啉。不同产物的选择性合成可以通过使用烯胺酮或烯胺酮/苯胺作为反应伙伴来实现。此外，与使用传统醛合成子的反应相比，雕白粉在更温和的条件下提供具有更高产率的产品方面显示出明显的优势。已经对反应过程进行了 GC-MS 分析，以探讨可能的反应机理。
• Annulative Nonaromatic Newman–Kwart-Type Rearrangement for the Synthesis of Sulfur Heteroaryls
  作者：Yunyun Liu、Leiling Deng、Haijin Guo、Jie-Ping Wan

  DOI：10.1021/acs.orglett.3c03581

  日期：2024.1.12

  By employing enaminones and thiuram disulfides as starting materials, the frontiers of Newman–Kwart rearrangement have been expanded to the alkenyl system for the first time. In addition, instead of leading to the formation of simple carbamothioates, the rearrangement has led to the unprecedented construction of S-heteroaryls. Depending on the differences in the enaminone structure, the efficient synthesis

  通过使用烯胺酮和二硫化秋兰姆作为起始原料，纽曼-夸特重排的前沿首次扩展到烯基体系。此外，重排并没有导致简单的硫代甲酸酯的形成，而是导致了前所未有的S-杂芳基的构建。根据烯胺酮结构的差异，实现了功能化异噻唑和噻吩的高效合成。
• Alberola, Angel; Calvo, Luis; Ortega, Alfonso Gonzalez, Heterocycles, 1999, vol. 51, # 11, p. 2675 - 2686
  作者：Alberola, Angel、Calvo, Luis、Ortega, Alfonso Gonzalez、Sadaba, M. Luisa、Sanudo, M. Carmen、Granda, Santiago Garcia、Rodriguez, Elena Garcia

  DOI：——

  日期：——
• Novel cAMP PDE III inhibitors: 1,6-naphthyridin-2(1H)-ones
  作者：Baldev Singh、George Y. Lesher、Kevin C. Pluncket、Edward D. Pagani、Donald C. Bode、Ross G. Bentley、Mary J. Connell、Linda T. Hamel、Paul J. Silver

  DOI：10.1021/jm00104a012

  日期：1992.12

  Two series of medorinone (3) analogs were prepared by modifications at C(2) and C(5). The C(2)-series was prepared from 2-chloro-5-methyl-1,6-naphthyridine (4) by replacement of the chloro group with various nucleophiles. The C(5)-series was prepared from 5-acyl-6-[2-(dimethylamino)ethenyl]-2-(1H)-pyridinone (11), 5-bromo-1,6-naphthyridin-2(1H)-one (17), and 1,3-diketones 19 and 27. 1,6-Naphthyridin-2(1H)-ones are novel inhibitors of cAMP PDE III. Modification of the carbonyl group of 3 or N-methylation at N(1) resulted in a dramatic loss of enzyme activity. Absence of the C(5)-methyl group of medorinone (3) or its shift to C(3) or C(7) also resulted in reduced activity. Substitution at C(3) also diminished activity. However, substitution at C(5) by a wide variety of substituents led to improvement of enzyme activity and several C(5)-substituted analogs were more potent than milrinone.