N-methyl-2-[13C]formylpyrrole | 200557-26-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-methyl-2-[13C]formylpyrrole
• CAS: 200557-26-2
• 化学式: C₆H₇NO
• 分子量: 110.117
• InChiKey: OUKQTRFCDKSEPL-HOSYLAQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.84
• 重原子数：
  8.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  22.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-甲基吡咯 、 N-methyl-2-[13C]formylpyrrole 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 tris(N-methyl-2-pyrrolyl)[13C]methane
  参考文献：
  名称：

  Pentoses and Hexoses as Sources of New Melanoidin-like Maillard Polymers

  摘要：

  N-Substituted pyrroles (1), 2-furaldehyde (2), and N-substituted 2-formylpyrroles (3), formed in pentose (hexose) Maillard systems, were identified as components of extraordinary polycondensation activity. The polycondensation was studied in model experiments with N-methylpyrrole (1a)/N-methyl-2-formylpyrrole (3a), N-(2-methoxycarbonylethyl)pyrrole (1b)/N-(2-methoxycarbonylethyl)-2-formylpyrrole (3b), N-methyl-2-formylpyrrole (3a), N-methylpyrrole (1a)/2-furaldehyde (2), and N-(2-methoxycarbonylethyl)pyrrole (1b)/2-furaldehyde (2), respectively. MALDI-TOF-MS spectra indicated regular oligomers of up to 15-30 methine-bridged N-methyl(or N-2-methoxycarbonylethyl)-pyrroles. With participation of aldehyde 2, furan rings instead of pyrrole rings were incorporated. The oligomers 5-11 were isolated and identified by MS and NMR techniques. A complementary experiment with N-methyl-2-[C-13]formylpyrrole ([(CHO)-C-13]-3a)/N-methylpyrrole (1a) was performed. The relevance of the new (type II) melanoidin-like oligomers/polymers in Maillard reactions is discussed and, in conclusion, a corresponding structure for native melanoidins is proposed. The oligomers 5, 6, 8, and 9 were tested for antioxidative activity in an iron(III) thiocyanate assay.

  DOI：

  10.1021/jf970973r
• 作为产物：
  描述：

  N-甲基吡咯 、 N,N-二甲基甲酰胺-羰基-13C 在 三氯氧磷 作用下， 生成 N-methyl-2-[13C]formylpyrrole
  参考文献：
  名称：

  New Melanoidin-like Maillard Polymers from 2-Deoxypentoses

  摘要：

  In the 2-deoxy-D-ribose/methyl 4-aminobutyrate Maillard system a trapped N-substituted 2-(hydroxymethyl)pyrrole is one of the major products. However, nontrapped representatives of this type of compound were hitherto not found in other Maillard model systems, indicating their extraordinary reactivity. Model experiments with 2-deoxy-D-ribose/methylamine enabled the detection of N-methyl-2-(hydroxymethyl)pyrrole (1) and some derived linear oligomers (2, 3) as minor components. Consequently, 1 was synthesized and its oligomerization studied under very mild acidic conditions. The deformylated dimeric bis(N-methyl-2-pyrrolyl)methane (2) and trimeric N-methyl-2,5-bis(N-methyl-2-pyrrolylmethyl)pyrrole (3) were characterized by GC/MS and NMR. Higher regular oligomers up to 6 N-methyl-2-pyrrolylmethyl units as well as corresponding dehydro-oligomers up to 12 units were identified by MALDI-TOF-MS. A complementary experiment starting with N-methyl-2-hydroxy[C-13]methylpyrrole ([(CH2OH)-C-13]-1) confirmed the structure and the oligomerization pathway. The possible significance of this type of model oligomer for the melanoidin formation in Maillard reactions is discussed. The antioxidative activity of the isolated dimer and trimer was tested in Fe(III)-thiocyanate and DPPH assays.

  DOI：

  10.1021/jf970657c