N-(2-methoxyethyl)-2-ethylpyrrole | 132163-62-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N-(2-methoxyethyl)-2-ethylpyrrole
• 英文别名: 2-Ethyl-1-(2-methoxyethyl)pyrrole
• CAS: 132163-62-3
• 化学式: C₉H₁₅NO
• 分子量: 153.224
• InChiKey: XGYNUPCLSBRKAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5,6-dichloro-hexan-3-one 在 sodium carbonate 、 三乙胺 作用下， 以 乙醚 、 水 、 苯 为溶剂， 反应 16.0h， 生成 N-(2-methoxyethyl)-2-ethylpyrrole
  参考文献：
  名称：

  Synthesis and properties of 1-(2-bromoethyl)-, 1-(2-alkoxyethyl)- and 1-(2-dialkylaminoethyl)2-alkylpyrroles

  摘要：

  DOI：

  10.1007/bf00480859

文献信息

• Independent Synthesis, Solution Behavior, and Studies on the Mechanism of Formation of a Primary Amine-Derived Fluorophore Representing Cross-linking of Proteins by (<i>E</i>)-4-Hydroxy-2-nonenal
  作者：Guozhang Xu、Yahua Liu、Lawrence M. Sayre

  DOI：10.1021/jo982523j

  日期：1999.8.1

  Lipid peroxidation in aging and degenerative disease results in the production of 4-hydroxy-2-alkenals that modify proteins and give rise to both protein cross-linking and fluorophore generation. Recent model studies demonstrated that the major ex/em 360/430 fluorophore formed from (E)-4-hydroxy-2-nonenal (HNE) or (E)-4-hydroxy-2-hexenal (HHE) and protein lysine-based amine is a 2-alkyl-2-hydroxy-1,2-dihydropyrrol-3-one iminium 1:2 cross-link (1), a structure that is further confirmed here using N-15-labeling, and which has pH stability characteristics the same as those of lipofuscin pigments isolated from human tissues. Fluorophore generation represents an overall four-electron oxidation, requires dioxygen, and is enhanced by the presence of Cu(II). The HNE-propylamine-derived fluorophore 1a was independently synthesized from either 3,4-dioxononanal (8) or (E)-4-oxo-2-nonenal (13), providing further evidence for its assigned structure and clues to how it forms from HNE. Mechanistic studies on HNE-derived fluorophore formation permit ruling out the initial reversible HNE-derived Schiff base Michael adduct (17) as an intermediate. In addition, the structurally related non-cross-link 2-pentyl-2-hydroxy-1,2-dihydropyrrol-3-one 9a that forms along with 1a from 8 does not form from HNE and does: not serve as a precursor to la in the HNE-amine reaction system. A mechanism involving two 2e oxidations following initial Schiff base formation is proposed that is consistent with intermediates independently accessed from 8 and 13.
• GADZHILY, R. A.;FEDOSEEV, V. M.;NADZHAFAROVA, R. A.;DZHAFAROV, V. G., XIMIYA GETEROTSIKL. SOED.,(1990) N, S. 1047-1049
  作者：GADZHILY, R. A.、FEDOSEEV, V. M.、NADZHAFAROVA, R. A.、DZHAFAROV, V. G.

  DOI：——

  日期：——
• Synthesis and properties of 1-(2-bromoethyl)-, 1-(2-alkoxyethyl)- and 1-(2-dialkylaminoethyl)2-alkylpyrroles
  作者：R. A. Gadzhily、V. M. Fedoseev、R. A. Nadzhafova、V. G. Dzhafarov

  DOI：10.1007/bf00480859

  日期：1990.8