2-(4-dimethylaminocinnamoyl)-2H-indane-1,3-dione | 20926-77-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-(4-dimethylaminocinnamoyl)-2H-indane-1,3-dione
• 英文别名: 2-(p-(N,N-dimethylamino)cinnamoyl)-1,3-indandione；2-(4-Dimethylaminocinnamoyl)-1.3-indandione；2-(4'-Dimethylaminocinnamoyl)indan-1,3-dione；2-[3-[4-(dimethylamino)phenyl]prop-2-enoyl]indene-1,3-dione
• CAS: 20926-77-6
• 化学式: C₂₀H₁₇NO₃
• 分子量: 319.36
• InChiKey: KIERCBOLSVXBEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-dimethylaminocinnamoyl)-2H-indane-1,3-dione 、 尿素 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以59%的产率得到2-[6-[4-(dimethylamino)phenyl]-2-oxo-5,6-dihydro-1H-pyrimidin-4-yl]indene-1,3-dione
  参考文献：
  名称：

  Synthesis pharmacological evaluation and docking studies of pyrimidine derivatives

  摘要：

  A new group of pyrimidine derivatives of indane-1,3-dione were synthesized aiming at the synthesis of new compounds acting as analgesic, anti-inflammatory and antimicrobial activity in a single component. The title compounds (3a-l) were synthesized from chalcone derivatives of indane-1,3-dione (2a-l) through cyclization reaction with urea. The synthesized compounds were characterized by FT-IR, H-1 NMR, mass spectral data, elemental analysis and evaluated for anti-inflammatory, analgesic, antibacterial and antifungal activities. The most active compound 3e, was evaluated for its ulcerogenicity. Good anti-inflammatory property was observed for chlorophenyl substituted pyrimidine derivatives. It mainly binds with Pro 218 of 1CX2, and the ligand could have caused much conformational changes in the protein structure than other derivatives. It also exhibits good analgesic and antimicrobial agent in a single component. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.050
• 作为产物：
  描述：

  对二甲氨基苯甲醛 、 2-乙基-1,3-氢化茚二酮 在 哌啶 作用下， 以60%的产率得到2-(4-dimethylaminocinnamoyl)-2H-indane-1,3-dione
  参考文献：
  名称：

  Synthesis, structure, spectral and coordination properties of a crown ether derivative of 1,3-indandione. A new structural evidence for the versatile reactivity of 2-acetyl-1,3-indandione

  摘要：

  摘要 本研究介绍了一种新的 1,3-茚二酮衍生物与共轭 N-苯基aza-15-冠-5 分子（4）的合成。研究人员解决了化合物 4 的晶体结构问题，并研究了其在各种溶剂以及碱性和碱土金属离子存在下的光学性质。采用量子化学（DFT）方法描述了所研究化合物及其复合物的结构和光学性质。研究结果表明，利用酸催化 2-乙酰基-1,3-茚二酮和相应的醛之间的醛醇反应合成化合物 4 时，伴随着一个意想不到的去乙酰化步骤。通过这种方式，N-苯基aza-15-冠-5 分子直接与 1,3-茚二酮片段共轭，而 1,3-茚二酮片段是众所周知的强电子受体。因此，4 的吸收光谱只受到与 Ba2+ 和 Sr2+ 离子络合的轻微影响。 补充材料： 本文的补充材料以单独文件形式提供：mmc1.pdf &

  DOI：

  10.1016/j.crci.2009.10.010

文献信息

• Synthesis, structure, spectral and coordination properties of a crown ether derivative of 1,3-indandione. A new structural evidence for the versatile reactivity of 2-acetyl-1,3-indandione
  作者：Anife Ahmedova、Nikola Burdzhiev、Samuele Ciattini、Elena Stanoeva、Mariana Mitewa

  DOI：10.1016/j.crci.2009.10.010

  日期：2010.10

  Résumé The current study describes the synthesis of a new 1,3-indandione derivative with conjugated N-phenylaza-15-crown-5 moiety (4). The crystal structure of compound 4 was solved and its optical properties were studied in various solvents and in presence of alkaline and alkaline-earth metal ions. Quantum chemical (DFT) methods were employed to describe the structure and the optical properties of the studied compound and its complexes. The obtained results indicated that the synthesis of compound 4 using acid-catalyzed aldol reaction between 2-acetyl-1,3-indandione and the corresponding aldehyde is accompanied with an unexpected deacetylation step. In this way, the N-phenylaza-15-crown-5 moiety is directly conjugated with the 1,3-indandione fragment, known as a very strong electron acceptor. Therefore, the absorption spectra of 4 are only slightly influenced by complexation with Ba2+ and Sr2+ ions. Supplementary Materials: Supplementary material for this article is supplied as a separate file: mmc1.pdf &

  摘要 本研究介绍了一种新的 1,3-茚二酮衍生物与共轭 N-苯基aza-15-冠-5 分子（4）的合成。研究人员解决了化合物 4 的晶体结构问题，并研究了其在各种溶剂以及碱性和碱土金属离子存在下的光学性质。采用量子化学（DFT）方法描述了所研究化合物及其复合物的结构和光学性质。研究结果表明，利用酸催化 2-乙酰基-1,3-茚二酮和相应的醛之间的醛醇反应合成化合物 4 时，伴随着一个意想不到的去乙酰化步骤。通过这种方式，N-苯基aza-15-冠-5 分子直接与 1,3-茚二酮片段共轭，而 1,3-茚二酮片段是众所周知的强电子受体。因此，4 的吸收光谱只受到与 Ba2+ 和 Sr2+ 离子络合的轻微影响。 补充材料： 本文的补充材料以单独文件形式提供：mmc1.pdf &
• Afsah,E. et al., Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1979, vol. 34, p. 502 - 506
  作者：Afsah,E. et al.

  DOI：——

  日期：——
• Synthesis pharmacological evaluation and docking studies of pyrimidine derivatives
  作者：D. Giles、Karki Roopa、F.R. Sheeba、P.M. Gurubasavarajaswamy、Goli Divakar、Thomas Vidhya

  DOI：10.1016/j.ejmech.2012.09.050

  日期：2012.12

  A new group of pyrimidine derivatives of indane-1,3-dione were synthesized aiming at the synthesis of new compounds acting as analgesic, anti-inflammatory and antimicrobial activity in a single component. The title compounds (3a-l) were synthesized from chalcone derivatives of indane-1,3-dione (2a-l) through cyclization reaction with urea. The synthesized compounds were characterized by FT-IR, H-1 NMR, mass spectral data, elemental analysis and evaluated for anti-inflammatory, analgesic, antibacterial and antifungal activities. The most active compound 3e, was evaluated for its ulcerogenicity. Good anti-inflammatory property was observed for chlorophenyl substituted pyrimidine derivatives. It mainly binds with Pro 218 of 1CX2, and the ligand could have caused much conformational changes in the protein structure than other derivatives. It also exhibits good analgesic and antimicrobial agent in a single component. (C) 2012 Elsevier Masson SAS. All rights reserved.