3,4-dihydroxy-β-methyl-β-nitrostyrene | 13662-96-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3,4-dihydroxy-β-methyl-β-nitrostyrene
• 英文别名: 4-(2-Nitroprop-1-enyl)benzene-1,2-diol
• CAS: 13662-96-9
• 化学式: C₉H₉NO₄
• 分子量: 195.175
• InChiKey: CBBBJLQAIWVLBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  86.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  硝基乙烷 、 3,4-二羟基苯甲醛 在 ammonium acetate 作用下， 反应 5.0h， 以35%的产率得到3,4-dihydroxy-β-methyl-β-nitrostyrene
  参考文献：
  名称：

  β-Nitrostyrene derivatives—a conformational study by combined Raman spectroscopy and ab initio MO calculations

  摘要：

  A complete conformational analysis of beta-nitrostyrene and beta-methyl-beta-nitrostyrene derivatives was carried out by Raman spectroscopy coupled to ab initio MO calculations. Apart from the optimised geometrical parameters of the most stable conformers of the molecules under study, the corresponding harmonic vibrational frequencies were calculated, as well as potential-energy profiles for several internal rotations within the molecules. At the light of these results, a complete assignment of the Raman spectra of the solid samples was performed. The conformational behaviour of this kind of systems was found to be mainly determined by the stabilising effect of pi-electron delocalisation. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2004.01.012

文献信息

• β-Nitrostyrene derivatives—a conformational study by combined Raman spectroscopy and ab initio MO calculations
  作者：R Calheiros、N Milhazes、F Borges、M.P.M Marques

  DOI：10.1016/j.molstruc.2004.01.012

  日期：2004.4

  A complete conformational analysis of beta-nitrostyrene and beta-methyl-beta-nitrostyrene derivatives was carried out by Raman spectroscopy coupled to ab initio MO calculations. Apart from the optimised geometrical parameters of the most stable conformers of the molecules under study, the corresponding harmonic vibrational frequencies were calculated, as well as potential-energy profiles for several internal rotations within the molecules. At the light of these results, a complete assignment of the Raman spectra of the solid samples was performed. The conformational behaviour of this kind of systems was found to be mainly determined by the stabilising effect of pi-electron delocalisation. (C) 2004 Elsevier B.V. All rights reserved.
• Exploring Nitrostyrene as a Scaffold for a New Class a of Monoamine Oxidase Inhibitors
  作者：Joana Reis、Catarina Oliveira、Nuno Milhazes、Dolores Vina、Fernanda Borges

  DOI：10.2174/157018012804586888

  日期：2012.12.1

  With the ultimate purpose of finding out the structural features that are relevant for MAO inhibitory activity and selectivity towards MAO-B isoform, a series of compounds encompassing a beta-nitrostyrene moiety was designed and the in vitro inhibitory activity was evaluated. In the present work, we report the synthesis and the pharmacological evaluation of a series of functionalized derivatives of beta-methyl-beta-nitrostyrene with distinct substitution patterns in the phenyl ring, namely hydroxyl, methoxy, benzyloxy and methylenedioxy. All the studied compounds were substituted in meta and para positions of the phenyl ring related to the nitrovinyl side chain. The synthesized compounds were evaluated towards both human MAO isoforms, displaying some of them activities in the low micromolar range. Particularly compound 6 (a methylenedioxy derivative) exhibits high potency and selectivity towards MAO-B.