3,4-二甲氧基乙酰乙酰苯胺 | 112854-82-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,4-二甲氧基乙酰乙酰苯胺
• 英文名称: acetoacetic acid-(3,4-dimethoxy-anilide)
• 英文别名: Acetessigsaeure-(3,4-dimethoxy-anilid)；N-(3,4-dimethoxyphenyl)-3-oxobutanamide
• CAS: 112854-82-7
• 化学式: C₁₂H₁₅NO₄
• mdl: MFCD01610159
• 分子量: 237.255
• InChiKey: BQCYBJWAQBWXCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-二甲氧基乙酰乙酰苯胺 在 硫酸 作用下， 以 水 为溶剂， 生成 6,7-dimethoxy-4-methyl-quinolin-2-ol
  参考文献：
  名称：

  Long-Wavelength-Absorbing and -Emitting Carbostyrils with High Fluorescence Quantum Yields

  摘要：

  Synthesis, absorption and fluorescence spectra, as well as quantum yields of a series of donor-acceptor-substituted carbostyrils (= quinolin-2(1H)-ones), are reported. Unprecedented strong absorption maxima (epsilon = 10000-20000) close to the visible spectrum, large Stokes shifts up to 130 nm, and quantum yields up to 0.7 are obtained with derivatives containing donor substituents at C(6) and C(7), and either one Ph substituent at C(3) or one CF3 residue at C(4). For analytical applications in biochemistry and medicine, N(1)-functionalization, or amidoacylation at C(3) in the case of the CF3 derivatives, is possible without a concomitant hypsochromic shift of their absorption and emission maxima. Semiempirical molecular-orbital calculations (AM1 for structures, ZINDO for electronic transition energies) prove to bit a suitable tool for the prediction of absorption properties of these compounds. The crystal-structure analysis of 6,7-dimethoxy-1-methyl-3-nitro-4-(trifluoromethyl)quinolin-2-(1H)-one (7) (C13H11F3N2O5, monoclinic, P2(1)/c, a = 12.372(2), b = 12.154(2), c = 10.119(2)Angstrom, beta = 112.95(2)degrees) shows that the NO2 group, squeezed between the CF3 and the C=O group, is oriented almost perpendicularly (87.8(4)degrees) to the ring plane. The intramolecular F ... N distance between the CF3 and the NO2 group is only 2.513(4)Angstrom.

  DOI：

  10.1002/(sici)1522-2675(19990908)82:9<1408::aid-hlca1408>3.0.co;2-q
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 3,4-二甲氧基苯胺 在 potassium hydroxide 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成 3,4-二甲氧基乙酰乙酰苯胺
  参考文献：
  名称：

  Phenothiazine and amide-ornamented dihydropyridinesviaa molecular hybridization approach: design, synthesis, biological evaluation and molecular docking studies

  摘要：

  一系列新颖的苯并噻唑基二氢吡啶二羧酰胺7a–7j通过采用多步合成策略合成，并通过物理和光谱技术进行表征。

  DOI：

  10.1039/c9nj03394g

文献信息

• Phenothiazine and amide-ornamented dihydropyridines<i>via</i>a molecular hybridization approach: design, synthesis, biological evaluation and molecular docking studies
  作者：Ramar Sivaramakarthikeyan、Shunmugam Iniyaval、Krishnaraj Padmavathy、Hui-Shan Liew、Chin-King Looi、Chun-Wai Mai、Chennan Ramalingan

  DOI：10.1039/c9nj03394g

  日期：——

  A series of novel phenothiazinyldihydropyridine dicarboxamides7a–7jwas synthesized by adopting a multi-step synthetic strategy and characterized through physical and spectral techniques.

  一系列新颖的苯并噻唑基二氢吡啶二羧酰胺7a–7j通过采用多步合成策略合成，并通过物理和光谱技术进行表征。
• Cu(TFA)₂-Catalyzed Oxidative Tandem Cyclization/1,2-Alkyl Migration of Enamino Amides for Synthesis of Pyrrolin-4-ones
  作者：Zhi-Jing Zhang、Zhi-Hui Ren、Yao-Yu Wang、Zheng-Hui Guan

  DOI：10.1021/ol4022222

  日期：2013.9.20

  A novel Cu(TFA)(2)-catalyzed oxidative tandem cyclization/1,2-alkyl migration of readily available enamino amides for the synthesis of pyrrolin-4-ones has been developed. The reaction tolerates a wide range of functional groups and is a reliable method for the rapid synthesis of substituted pyrrolin-4-ones in high yields under mild conditions.
• Lions, Journal and Proceedings - Royal Society of New South Wales, 1938, vol. 71, p. 242,248
  作者：Lions

  DOI：——

  日期：——
• THE SEARCH FOR SUPERIOR ANTIMALARIALS. II. THE SYNTHESIS OF 6,7-DIMETHOXYQUINOLINE DERIVATIVES AND OF SOME INCIDENTAL COMPOUNDS
  作者：KURT C. FRISCH、MARSTON TAYLOR BOGERT

  DOI：10.1021/jo01186a006

  日期：1944.7
• Phenothiazine and amide-ornamented novel nitrogen heterocyclic hybrids: synthesis, biological and molecular docking studies
  作者：Ramar Sivaramakarthikeyan、Ayyanar Karuppasamy、Shunmugam Iniyaval、Krishnaraj Padmavathy、Wei-Meng Lim、Chun-Wai Mai、Chennan Ramalingan

  DOI：10.1039/c9nj05489h

  日期：——

  standard diclofenac sodium. A hybrid integrated with a para-fluorophenyl carboxamide moiety (28) showed the highest DPPH radical scavenging activity among the chemical entities synthesized. Furthermore, the results of anticancer evaluations implied that the hybrid tethered with a phenyl carboxamide structural unit (29) exerted superior activity when compared with other hybrids against the pancreatic cancer

  新型杂合体的合成，即吩噻嗪和酰胺修饰的氮杂环（25-34）已利用多步合成方案完成，并基于物理和光谱技术建立了结构。其中，杂种具有间-硝基（26），对-氟（28），间-和对-甲基（31），邻-溴（33）和邻-和对-二甲基（34）。）苯基羧酰胺支架比标准双氯芬酸钠具有更好的抗炎特性。与对-氟苯基羧酰胺部分（28）整合的杂化物显示出在合成的化学实体中最高的DPPH自由基清除活性。此外，抗癌评估的结果表明，与苯基羧酰胺结构单元（29）相连的杂合体与其他杂合体相比，具有针对胰腺癌细胞SW1990和AsPC1的优异活性。杂种29与B细胞淋巴瘤2之间的分子对接反映了其明显的结合亲和力（−8.84 kcal mol -1）。结果表明，这些化学实体可以用作有效的生物试剂和/或用于构建有效的生物试剂的有效中间体。