8-formyl-7-hydroxy-4-methyl-2H-<1>benzopyran-2-one oxime | 91917-59-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 8-formyl-7-hydroxy-4-methyl-2H-<1>benzopyran-2-one oxime
• 英文别名: 7-hydroxy-4-methyl-2-oxo-2H-chromene-8-carbaldehyde oxime；7-hydroxy-8-(hydroxyimino-methyl)-4-methyl-coumarin；7-Hydroxy-8-(hydroxyimino-methyl)-4-methyl-cumarin；7-hydroxy-8-[(E)-hydroxyiminomethyl]-4-methylchromen-2-one
• CAS: 91917-59-8
• 化学式: C₁₁H₉NO₄
• 分子量: 219.197
• InChiKey: KIEOJHDWODEJNI-LFYBBSHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.62
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  83.03
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  羟甲香豆素 在 乌洛托品 、 羟胺 、 溶剂黄146 作用下， 生成 8-formyl-7-hydroxy-4-methyl-2H-<1>benzopyran-2-one oxime
  参考文献：
  名称：

  Nesmejanow et al., Zhurnal Obshchei Khimii, 1937, vol. 7, p. 2767,2770

  摘要：

  DOI：

文献信息

• Synthesis, characterization, anti-diabetic potential and DFT studies of 7-hydroxy-4-methyl-2-oxo-2H-chromene-8-carbaldehyde oxime
  作者：Seyed Mohammad Bagher Hosseini Ghazvini、Parvin Safari、Akbar Mobinikhaledi、Hassan Moghanian、Hassan Rasouli

  DOI：10.1016/j.saa.2018.07.009

  日期：2018.12

  A new compound named 7-hydroxy-4-methyl-2-oxo-2H-chromene-8-carbaldehyde oxime (7-Oxime) was synthesized and characterized by FT-IR, FT-Raman, H-1 NMR and C-13 NMR techniques. The conformer possibilities were studied to find the most stable conformer and its molecular geometry. Then, the dimer form of the most stable monomer was built and optimized. Density functional theory (DFT) B3LYP method with 6-311++G(d, p) basis set was applied to analyze the molecular electrostatic potential (MEP), HOMO and LUMO orbitals, the vibrational wavenumbers, the infrared intensities, the Raman scattering activities and several thermodynamic properties (at different temperatures). The stability of the molecule derived from hyperconjugative interactions and charge delocalization has been analyzed by using natural bond orbital (NBO) analysis. In order to find the possible inhibitory activity of 7-Oxime, an accurate molecular blind docking simulation was performed. The results indicated that the mentioned compound has a good binding affinity to interact with the active sites of human a-glucosidase and alpha-amylase. For the first time, our computational finding suggests that this compound has a potential to be used as a supplementary agent in the pre-management of diabetes mellitus. (C) 2018 Elsevier B.V. All rights reserved.