2-[2-(2-methoxyethoxy)ethoxy]ethyl 2-(3-methyl-2-oxo-1,2-dihydropyridin-1-yl)acetate | 1508071-18-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[2-(2-methoxyethoxy)ethoxy]ethyl 2-(3-methyl-2-oxo-1,2-dihydropyridin-1-yl)acetate
• 英文别名: 2-[2-(2-Methoxyethoxy)ethoxy]ethyl 2-(3-methyl-2-oxopyridin-1-yl)acetate；2-[2-(2-methoxyethoxy)ethoxy]ethyl 2-(3-methyl-2-oxopyridin-1-yl)acetate
• CAS: 1508071-18-8
• 化学式: C₁₅H₂₃NO₆
• 分子量: 313.351
• InChiKey: ZAJRBIDCPRXZQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[2-(2-methoxyethoxy)ethoxy]ethyl 2-(3-methyl-2-oxo-1,2-dihydropyridin-1-yl)acetate 在 氧气 、 tetraphenylporphyrin 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以70%的产率得到2-[2-(2-methoxyethoxy)ethoxy]ethyl 2-{1-methyl-6-oxo-2,3-dioxa-5-azabicyclo[2.2.2]oct-7-en-5-yl}acetate
  参考文献：
  名称：

  Controlled Oxygen Release from Pyridone Endoperoxides Promotes Cell Survival under Anoxic Conditions

  摘要：

  In tissue engineering, survival of larger constructs remains challenging due to limited supply of oxygen caused by a lack of early vascularization. Controlled release of oxygen from small organic molecules represents a possible strategy to prevent cell death under anoxic conditions. A comprehensive study of methylated pyridone-derived endoperoxides has led to the development of water-soluble molecules that undergo retro-Diels-Alder reactions in aqueous environment releasing oxygen in high yield and with half-lives of up to 13 h. These molecules in combination with vitamin C as singlet oxygen quencher significantly improved survival of 3T3 fibroblasts and rat smooth muscle cells challenged with oxygen-depleted conditions.

  DOI：

  10.1021/jm4016137
• 作为产物：
  描述：

  三甘醇单甲醚 在 4-二甲氨基吡啶 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[2-(2-methoxyethoxy)ethoxy]ethyl 2-(3-methyl-2-oxo-1,2-dihydropyridin-1-yl)acetate
  参考文献：
  名称：

  Controlled Oxygen Release from Pyridone Endoperoxides Promotes Cell Survival under Anoxic Conditions

  摘要：

  In tissue engineering, survival of larger constructs remains challenging due to limited supply of oxygen caused by a lack of early vascularization. Controlled release of oxygen from small organic molecules represents a possible strategy to prevent cell death under anoxic conditions. A comprehensive study of methylated pyridone-derived endoperoxides has led to the development of water-soluble molecules that undergo retro-Diels-Alder reactions in aqueous environment releasing oxygen in high yield and with half-lives of up to 13 h. These molecules in combination with vitamin C as singlet oxygen quencher significantly improved survival of 3T3 fibroblasts and rat smooth muscle cells challenged with oxygen-depleted conditions.

  DOI：

  10.1021/jm4016137

文献信息

• 一种甲基酮衍生物及其制备方法与应用
  申请人：苏州大学

  公开号：CN106496130B

  公开（公告）日：2019-09-20

  本发明公开了一种甲基酮衍生物及其制备方法与应用，将酮衍生物、有机过氧化物溶于溶剂中，于80‑130℃反应，获得甲基嘧啶酮和甲基吡啶酮衍生物。本发明使用酮衍生物为起始物，原料易得、种类很多；利用本发明的方法得到的产物类型多样，既可以直接使用、又可以用于其他进一步的反应。本发明方法无金属参与，适合于制药工艺。本发明方法路线简短、反应条件温和、反应操作和后处理过程简单、产率较高，适合于规模化生产。
• Controlled Oxygen Release from Pyridone Endoperoxides Promotes Cell Survival under Anoxic Conditions
  作者：Sebastian Benz、Sarah Nötzli、Jay S. Siegel、Daniel Eberli、Henning J. Jessen

  DOI：10.1021/jm4016137

  日期：2013.12.27

  In tissue engineering, survival of larger constructs remains challenging due to limited supply of oxygen caused by a lack of early vascularization. Controlled release of oxygen from small organic molecules represents a possible strategy to prevent cell death under anoxic conditions. A comprehensive study of methylated pyridone-derived endoperoxides has led to the development of water-soluble molecules that undergo retro-Diels-Alder reactions in aqueous environment releasing oxygen in high yield and with half-lives of up to 13 h. These molecules in combination with vitamin C as singlet oxygen quencher significantly improved survival of 3T3 fibroblasts and rat smooth muscle cells challenged with oxygen-depleted conditions.