(S)-1-methyl-5-(3-pyridil)pyrrolidin-2-selenone | 1565853-95-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (S)-1-methyl-5-(3-pyridil)pyrrolidin-2-selenone
• 英文别名: selenonicotine；nicotine selenolactam；(5S)-1-methyl-5-pyridin-3-ylpyrrolidine-2-selone
• CAS: 1565853-95-3
• 化学式: C₁₀H₁₂N₂Se
• 分子量: 239.179
• InChiKey: OMBKGVUIGKHLIQ-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.15
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-methyl-5-(3-pyridil)pyrrolidin-2-selenone 、 胆酸 以 甲醇 为溶剂， 反应 12.0h， 以78%的产率得到(S)-1-methyl-5-(pyridin-3-yl)pyrrolidine-2-selenone (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate
  参考文献：
  名称：

  Synthesis and haemolytic activity of novel salts made of nicotine alkaloids and bile acids

  摘要：

  A series of novel salts made of nicotine alkaloids and bile acids were synthesized and their haemolytic activity was examined in vitro using human erythrocytes. All compounds were characterized by spectroscopic methods. The novel salts show membrane-perturbing properties inducing the erythrocyte shape alterations and haemolysis in dose-dependent manner. Nicotine decreases the membrane interacting potential of bile acids in the novel compounds. The presence of sulfur or selenium atom in the nicotine molecule affects the haemolytic activity of its novel salts depending on the hydrophobicity of bile acids. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.005
• 作为产物：
  描述：

  吡啶吡咯酮 在 Woollins 试剂 作用下， 生成 (S)-1-methyl-5-(3-pyridil)pyrrolidin-2-selenone
  参考文献：
  名称：

  Synthesis and haemolytic activity of novel salts made of nicotine alkaloids and bile acids

  摘要：

  A series of novel salts made of nicotine alkaloids and bile acids were synthesized and their haemolytic activity was examined in vitro using human erythrocytes. All compounds were characterized by spectroscopic methods. The novel salts show membrane-perturbing properties inducing the erythrocyte shape alterations and haemolysis in dose-dependent manner. Nicotine decreases the membrane interacting potential of bile acids in the novel compounds. The presence of sulfur or selenium atom in the nicotine molecule affects the haemolytic activity of its novel salts depending on the hydrophobicity of bile acids. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.005

文献信息

• Chalcogen analogues of nicotine lactam studied by NMR, FTIR, DFT and X-ray methods
  作者：Beata Jasiewicz、Karolina Malczewska-Jaskóła、Iwona Kowalczyk、Beata Warżajtis、Urszula Rychlewska

  DOI：10.1016/j.saa.2014.02.158

  日期：2014.7

  The selenoanalogue of nicotine has been synthesized and characterized by spectroscopic and X-ray diffraction methods. The crystals of selenonicotine are isomorphic with the thionicotine homologue and consist of molecules engaged in columnar pi center dot center dot center dot pi stacking interactions between antiparallely arranged pyridine moieties. These interactions, absent in other crystals containing nicotine fragments, seem to be induced by the presence of a lactam group. The molecular structures in the vacuum of the oxo-, thio- and selenonicotine homologues have been calculated by the DFT method and compared with the available X-ray data. The delocalized structure of thionicotine is stabilized by intramolecular C-H center dot center dot center dot S hydrogen bond, which becomes weaker in the partial zwitterionic resonance structure of selenonicotine in favor of multiple C-H center dot center dot center dot Se intermolecular hydrogen-bonds. The calculated data allow a complete assignment of vibration modes in the solid state FTIR spectra. The H-1 and C-13 NMR chemical shifts were calculated by the MO method with B3LYP/6-311G(3df) level. A comparison between experimental and calculated theoretical results indicates that the density functional B3LYP method provided satisfactory results for predicting FTIR, H-1, C-13 NMR spectra properties. (C) 2014 Elsevier B.V. All rights reserved.
• Synthesis and haemolytic activity of novel salts made of nicotine alkaloids and bile acids
  作者：Beata Jasiewicz、Lucyna Mrówczyńska、Karolina Malczewska-Jaskóła

  DOI：10.1016/j.bmcl.2014.01.005

  日期：2014.2

  A series of novel salts made of nicotine alkaloids and bile acids were synthesized and their haemolytic activity was examined in vitro using human erythrocytes. All compounds were characterized by spectroscopic methods. The novel salts show membrane-perturbing properties inducing the erythrocyte shape alterations and haemolysis in dose-dependent manner. Nicotine decreases the membrane interacting potential of bile acids in the novel compounds. The presence of sulfur or selenium atom in the nicotine molecule affects the haemolytic activity of its novel salts depending on the hydrophobicity of bile acids. (C) 2014 Elsevier Ltd. All rights reserved.