1-(α-hydroxybenzyl)-2,3-di(4-chlorophenyl)indolizine-7-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(α-hydroxybenzyl)-2,3-di(4-chlorophenyl)indolizine-7-carbonitrile
• 英文别名: 2,3-Bis(4-chlorophenyl)-1-[hydroxy(phenyl)methyl]indolizine-7-carbonitrile
• 化学式: C₂₈H₁₈Cl₂N₂O
• 分子量: 469.37
• InChiKey: BODFBUQHHNDVHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  48.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-bromo-2,3-di(4-chlorophenyl)indolizine-7-carbonitrile 、 苯甲醛 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以71%的产率得到1-(α-hydroxybenzyl)-2,3-di(4-chlorophenyl)indolizine-7-carbonitrile
  参考文献：
  名称：

  Electrochemical studies of biologically active indolizines

  摘要：

  The electrochemical behavior of indolizine ethers, esters, tosylates, sulfonates and other indolizine and azaindolizine derivatives has been investigated by cyclic voltammetry and preparative electrolysis. The cyclic voltammetric data show that the E degrees values, taken as the midpoints between the anodic and cathodic peak potentials, are sensitive to the identities of the substituents at C-1, C-2 and C-7 positions. The E degrees values have been correlated with the Hammett substituent parameters. As expected, low E degrees values are seen for electron donating substituents and higher E degrees values are seen for electron withdrawing substituents. The cyclic voltammograms of indolizine derivatives with an oxygen atom connected to the CA position exhibit a one-electron reversible oxidation and a further, less well-defined, one-electron irreversible oxidation at higher E degrees values. The cyclic voltammograms of indolizines with hydrogen atom or thienyl substituents connected to the G I position exhibit only a one-electron irreversible oxidation. Electrochemical bulk oxidations of indolizines with an oxygen atom at the C-1 position afforded oxoindolizinium salts in decent yields, whereas indolizines with a hydrogen atom at C-1 afforded 1,1' dimers of indolizines as products in good yields. Bulk oxidation of 1-(alpha-hydroxybenzyl)-2,3-diphenylindolizine-7-carbonitfile afforded an unexpected ketone product in which the carbonyl group of the indolizine is connected at C-8 instead of at the C-I position of the starting material. The findings described herein support our hypothesis that certain indolizine derivatives may inhibit lipid peroxidation by an electron transfer mechanism. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.02.078

文献信息

• Electrochemical studies of biologically active indolizines
  作者：Solomon Teklu、Lise-Lotte Gundersen、Frode Rise、Mats Tilset

  DOI：10.1016/j.tet.2005.02.078

  日期：2005.5

  The electrochemical behavior of indolizine ethers, esters, tosylates, sulfonates and other indolizine and azaindolizine derivatives has been investigated by cyclic voltammetry and preparative electrolysis. The cyclic voltammetric data show that the E degrees values, taken as the midpoints between the anodic and cathodic peak potentials, are sensitive to the identities of the substituents at C-1, C-2 and C-7 positions. The E degrees values have been correlated with the Hammett substituent parameters. As expected, low E degrees values are seen for electron donating substituents and higher E degrees values are seen for electron withdrawing substituents. The cyclic voltammograms of indolizine derivatives with an oxygen atom connected to the CA position exhibit a one-electron reversible oxidation and a further, less well-defined, one-electron irreversible oxidation at higher E degrees values. The cyclic voltammograms of indolizines with hydrogen atom or thienyl substituents connected to the G I position exhibit only a one-electron irreversible oxidation. Electrochemical bulk oxidations of indolizines with an oxygen atom at the C-1 position afforded oxoindolizinium salts in decent yields, whereas indolizines with a hydrogen atom at C-1 afforded 1,1' dimers of indolizines as products in good yields. Bulk oxidation of 1-(alpha-hydroxybenzyl)-2,3-diphenylindolizine-7-carbonitfile afforded an unexpected ketone product in which the carbonyl group of the indolizine is connected at C-8 instead of at the C-I position of the starting material. The findings described herein support our hypothesis that certain indolizine derivatives may inhibit lipid peroxidation by an electron transfer mechanism. (c) 2005 Elsevier Ltd. All rights reserved.