1-(2,2-dimethylpropyl)-2,3,4,5-tetramethylpyrrole

• 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-(2,2-dimethylpropyl)-2,3,4,5-tetramethylpyrrole
• 英文别名: 1-(2,2-Dimethylpropyl)-2,3,4,5-tetramethylpyrrole
• 化学式: C₁₃H₂₃N
• 分子量: 193.332
• InChiKey: MBQAYVWULXZWOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  特戊胺 、 3,4-二甲基-己烷-2,5-二酮 以 乙醇 为溶剂， 反应 10.0h， 生成 1-(2,2-dimethylpropyl)-2,3,4,5-tetramethylpyrrole
  参考文献：
  名称：

  Novel 2,5-Hexanedione Analogues. Substituent-Induced Control of the Protein Cross-Linking Potential and Oxidation Susceptibility of the Resulting Primary Amine-Derived Pyrroles

  摘要：

  The neurotoxic gamma -diketone, 2,5-hexanedione (2,5-HD), induces neurofilamentous swellings at prenodal sites in proximal axons as a consequence of pyrrolation of lysine E-amino groups on neurofilament proteins. However, there is disagreement as to whether pyrrole formation and the associated alteration of noncovalent interactions is sufficient to cause neurofilament accumulation, or whether pyrrole autoxidation and subsequent protein-protein cross-linking is an obligatory event. To investigate gamma -diketones that might form pyrroles inert to autoxidative-induced cross-linking, we synthesized 1,1,1-trifluoro-2,5-hexanedione, 3-(trifluoromethyl)-2,5-hexanedione (3-TFMHD), and two 3-(dialkylaminocarbonyl)-2,5-diketones and assessed their rates of pyrrole formation with amines, the oxidation susceptibility of the resulting pyrroles, and the protein cross-linking potential in vitro, relative to those of 3-methyl-2,5-hexanedione. 1,1,1-Trifluoro-2,5-hexanedione does not form pyrroles, but the three 2,5-HD analogues with an electron-withdrawing 3-substituent all rapidly formed pyrroles that were inert to autoxidation. Although 3-TMFHD nonetheless still induced cross-linking of ribonuclease A, by a nonoxidative mechanism independent of the pyrrole, the two 3-(dialkylaninocarbonyl)-2,5-diketones did not exhibit any protein cross-linking. As these two gamma -diketones possess aqueous-organic partitioning properties similar to those of 2,5-HD, they should serve as useful mechanistic probes in further studies.

  DOI：

  10.1021/tx000169q

文献信息

• Novel 2,5-Hexanedione Analogues. Substituent-Induced Control of the Protein Cross-Linking Potential and Oxidation Susceptibility of the Resulting Primary Amine-Derived Pyrroles
  作者：Guozhang Xu、Malvinder P. Singh、Damodaragounder Gopal、Lawrence M. Sayre

  DOI：10.1021/tx000169q

  日期：2001.3.1

  The neurotoxic gamma -diketone, 2,5-hexanedione (2,5-HD), induces neurofilamentous swellings at prenodal sites in proximal axons as a consequence of pyrrolation of lysine E-amino groups on neurofilament proteins. However, there is disagreement as to whether pyrrole formation and the associated alteration of noncovalent interactions is sufficient to cause neurofilament accumulation, or whether pyrrole autoxidation and subsequent protein-protein cross-linking is an obligatory event. To investigate gamma -diketones that might form pyrroles inert to autoxidative-induced cross-linking, we synthesized 1,1,1-trifluoro-2,5-hexanedione, 3-(trifluoromethyl)-2,5-hexanedione (3-TFMHD), and two 3-(dialkylaminocarbonyl)-2,5-diketones and assessed their rates of pyrrole formation with amines, the oxidation susceptibility of the resulting pyrroles, and the protein cross-linking potential in vitro, relative to those of 3-methyl-2,5-hexanedione. 1,1,1-Trifluoro-2,5-hexanedione does not form pyrroles, but the three 2,5-HD analogues with an electron-withdrawing 3-substituent all rapidly formed pyrroles that were inert to autoxidation. Although 3-TMFHD nonetheless still induced cross-linking of ribonuclease A, by a nonoxidative mechanism independent of the pyrrole, the two 3-(dialkylaninocarbonyl)-2,5-diketones did not exhibit any protein cross-linking. As these two gamma -diketones possess aqueous-organic partitioning properties similar to those of 2,5-HD, they should serve as useful mechanistic probes in further studies.