1H-Pyrrole-1-hexanoic acid, 2,5-dihydro-3,4-dimethyl-2,5-dioxo- | 63751-10-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1H-Pyrrole-1-hexanoic acid, 2,5-dihydro-3,4-dimethyl-2,5-dioxo-
• 英文别名: 6-(3,4-dimethyl-2,5-dioxopyrrol-1-yl)hexanoic acid
• CAS: 63751-10-0
• 化学式: C₁₂H₁₇NO₄
• 分子量: 239.271
• InChiKey: LQRDWDFBWXZAOS-UHFFFAOYSA-N

物化性质

• 沸点：
  415.9±28.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1H-Pyrrole-1-hexanoic acid, 2,5-dihydro-3,4-dimethyl-2,5-dioxo- 在 phosphate buffer pH 7 、 三氟化硼 作用下， 以 甲醇 为溶剂， 反应 11.17h， 生成 methyl 6-<3,4-dimethyl-3-<<2-(methoxycarbonyl)-2-(acetylamino)ethyl>thio>-2,5-dioxopyrrolidin-1-yl>hexanoate
  参考文献：
  名称：

  Structure and Potential Crosslinking Reactivity of a New Pentose-Specific Maillard Product

  摘要：

  The Maillard reaction of model compounds for peptide-bound lysine (4-aminobutyric acid, 6-aminocaproic acid, N-alpha-acetyl-L-lysine) with reducing sugars (D-ribose, D-xylose, D-arabinose, D-glucose, D-fructose, D-glyceraldehyde) was investigated under both stringent and mild conditions. With pentoses the corresponding omega-(dimethylmaleimido)carboxylic acids 1-3 were identified as substantial, hitherto unknown components by GC/MS and NMR. Their structure was confirmed by synthesis. A pathway to compounds 1-3 was derived from the results of 4-aminobutyric acid/[1-C-13]-D-arabinose isotopic labeling experiments. The new N-(dimethylmaleoyl)-omega-aminocarboxylic acid derivatives are shown to react under very mild conditions (pH 7, 32 degrees C) with thiols (methyl 3-mercaptopropionate, N-alpha-acetyl-L-cysteine methyl ester) to form the addition products 4-6. This reaction demonstrates that compounds of type 1-3 can be considered as potential protein cross-linkers in Maillard reactions.

  DOI：

  10.1021/jf00048a009
• 作为产物：
  描述：

  2,3-二甲基马来酸酐 、 6-氨基己酸 在 sodium hydroxide 作用下， 生成 1H-Pyrrole-1-hexanoic acid, 2,5-dihydro-3,4-dimethyl-2,5-dioxo-
  参考文献：
  名称：

  Structure and Potential Crosslinking Reactivity of a New Pentose-Specific Maillard Product

  摘要：

  The Maillard reaction of model compounds for peptide-bound lysine (4-aminobutyric acid, 6-aminocaproic acid, N-alpha-acetyl-L-lysine) with reducing sugars (D-ribose, D-xylose, D-arabinose, D-glucose, D-fructose, D-glyceraldehyde) was investigated under both stringent and mild conditions. With pentoses the corresponding omega-(dimethylmaleimido)carboxylic acids 1-3 were identified as substantial, hitherto unknown components by GC/MS and NMR. Their structure was confirmed by synthesis. A pathway to compounds 1-3 was derived from the results of 4-aminobutyric acid/[1-C-13]-D-arabinose isotopic labeling experiments. The new N-(dimethylmaleoyl)-omega-aminocarboxylic acid derivatives are shown to react under very mild conditions (pH 7, 32 degrees C) with thiols (methyl 3-mercaptopropionate, N-alpha-acetyl-L-cysteine methyl ester) to form the addition products 4-6. This reaction demonstrates that compounds of type 1-3 can be considered as potential protein cross-linkers in Maillard reactions.

  DOI：

  10.1021/jf00048a009

文献信息

• US4079041A
  申请人：——

  公开号：US4079041A

  公开（公告）日：1978-03-14
• US4163097A
  申请人：——

  公开号：US4163097A

  公开（公告）日：1979-07-31
• US4158730A
  申请人：——

  公开号：US4158730A

  公开（公告）日：1979-06-19
• US4158731A
  申请人：——

  公开号：US4158731A

  公开（公告）日：1979-06-19
• [EN] IMIDO PERESTERS AS INITIATORS OF POLYMERIZATION PROCESSES<br/>[FR] IMIDO-PERESTERS SERVANT D'INITIATEURS DE PROCESSUS DE POLYMERISATION
  申请人：AKZO NOBEL N.V.

  公开号：WO1997003962A1

  公开（公告）日：1997-02-06

  (EN) A new group of imido peresters is provided which are represented by general formula (I), which are highly interesting for industrial applications, such as initiation of polymerization processes, polymer modification and cross-linking. For example, the compounds show excellent properties in producing high molecular weight polystyrene (co)-polymers, the cross-linking of rubbers and elastomers, and the curing of unsaturated polyesters. Also compositions are provided comprising at least one imido perester of formula (I) as well as methods of preparing these peresters.(FR) Nouveau groupe d'imido-peresters de formule générale (I), très intéressants pour certaines applications industrielles, telles que l'initiation des processus de polymérisation, la modification des polymères et la réticulation. Ainsi, ils s'avèrent très utiles à la production de (co)polymères polystyrène de masse moléculaire élevée, la réticulation des caoutchoucs et élastomères, et la vulcanisation des polyesters insaturés. Sont également décrites des compositions comportant au moins un imido-perester de formule (I), ainsi que des procédés de préparation de ces peresters.