1-hydroxy-1,5-dihydro-2H-pyrrol-2-one | 1391057-03-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 1-hydroxy-1,5-dihydro-2H-pyrrol-2-one
• 英文别名: hydroxy-1,5-dihydro-2H-pyrrol-2-one；hydroxy-1,5-dihydro-pyrrol-2-one；hydroxyl pyrroline-2-one；hydroxyl-pyrrolin-2-one；hydroxypyrroline-2-one；hydroxypyrrolin-2-one；Hydroxy-3-pyrrolin-2-one；1-hydroxy-2H-pyrrol-5-one
• CAS: 1391057-03-6
• 化学式: C₄H₅NO₂
• 分子量: 99.0892
• InChiKey: UNBFIJXMQSWODB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  C₁₂H₁₃NO₃ 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 1-hydroxy-1,5-dihydro-2H-pyrrol-2-one
  参考文献：
  名称：

  Toward a fragment-based approach to MMPs inhibitors: an expedite and efficient synthesis of N-hydroxylactams

  摘要：

  Matrix metalloproteinases (MMPs), a class of zinc-enzymes over-activated in many pathologies, such as arthritis and cancer, can be efficiently inhibited by a variety of molecules bearing zinc-binding groups (ZBGs). The hydroxamic acid moiety represents one of the most potent and widely exploited ZBG but the poor target selectivity and in vivo toxicity have tempered the initial enthusiasm for this class of potential therapeutics. These drawbacks might be circumvented, at least in part, by increasing the structural constraints around the hydroxamic moiety. Following this strategy we designed and prepared N-hydroxylactam molecules of different size through a synthetic protocol based on a ring closing metathesis amenable to a fragment-based approach potentially leading to a large molecular diversity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.05.124