4-(3,4-dimethyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoic acid | 121487-63-6

• 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: 4-(3,4-dimethyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoic acid
• 英文别名: 4-(3,4-Dimethyl-2,5-dioxopyrrol-1-yl)butanoic acid
• CAS: 121487-63-6
• 化学式: C₁₀H₁₃NO₄
• 分子量: 211.218
• InChiKey: AIHPMLDWBAVIAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  4-(3,4-dimethyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoic acid 在 氯化亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 33.16h， 生成 methyl (1R,7aR)-7a-((tert-butyldimethylsilyl)oxy)-6,7-dimethyl-5-oxo-2,3,5,7a-tetrahydro-1H-pyrrolizine-1-carboxylate
  参考文献：
  名称：

  Skeletal Analogues of UCS1025A and B by Cyclization of Maleimides: Synthesis and Biological Activity

  摘要：

  摘要：应用一种直接环合成方法，利用内环醛缩反应和酮基硅醚在远离的亚胺基团上反应，形成UCS1025A和B的核心骨架，有效地提供了一系列取代类似物的访问途径；有趣的是它们完全缺乏对MRSA（革兰阳性）和大肠杆菌（革兰阴性）细菌菌株的抗菌活性。

  DOI：

  10.1055/s-0040-1719876
• 作为产物：
  描述：

  2,3-二甲基马来酸酐 、 4-氨基丁酸 在 溶剂黄146 作用下， 反应 6.0h， 以100%的产率得到4-(3,4-dimethyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoic acid
  参考文献：
  名称：

  Skeletal Analogues of UCS1025A and B by Cyclization of Maleimides: Synthesis and Biological Activity

  摘要：

  摘要：应用一种直接环合成方法，利用内环醛缩反应和酮基硅醚在远离的亚胺基团上反应，形成UCS1025A和B的核心骨架，有效地提供了一系列取代类似物的访问途径；有趣的是它们完全缺乏对MRSA（革兰阳性）和大肠杆菌（革兰阴性）细菌菌株的抗菌活性。

  DOI：

  10.1055/s-0040-1719876

文献信息

• Structure and Potential Crosslinking Reactivity of a New Pentose-Specific Maillard Product
  作者：Roland Tressl、Georg Wondrak、Evelyn Kersten、Dieter Rewicki

  DOI：10.1021/jf00048a009

  日期：1994.12

  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.
• Bismaleimides comprising mesogenic groups and oligomeric liquid crystalline bismaleimides
  申请人：DAINIPPON INK AND CHEMICALS, INC.

  公开号：EP1016659B1

  公开（公告）日：2003-09-24
• US6169186B1
  申请人：——

  公开号：US6169186B1

  公开（公告）日：2001-01-02
• [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.
• Skeletal Analogues of UCS1025A and B by Cyclization of Maleimides: Synthesis and Biological Activity
  作者：Mark G. Moloney、Lewis T. Ibbotson、Kirsten E. Christensen、Miroslav Genov、Alexander Pretsch、Dagmar Pretsch

  DOI：10.1055/s-0040-1719876

  日期：2022.3

  Application of a direct ring-closing approach which exploits an intramolecular aldol reaction with a ketene silyl acetal onto a remote imide function leading to the core skeleton of UCS1025A and B effectively provides access to small library of substituted analogues; of interest is their complete lack of antibacterial activity against MRSA (Gram+) and E. coli (Gram–) bacterial strains.

  摘要：应用一种直接环合成方法，利用内环醛缩反应和酮基硅醚在远离的亚胺基团上反应，形成UCS1025A和B的核心骨架，有效地提供了一系列取代类似物的访问途径；有趣的是它们完全缺乏对MRSA（革兰阳性）和大肠杆菌（革兰阴性）细菌菌株的抗菌活性。