2-[2-(2-methoxyethoxy)ethoxy]ethyl 2-(3,6-dimethyl-2-oxo-1,2-dihydropyridin-1-yl)acetate | 1508071-25-7

• 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-(3,6-dimethyl-2-oxo-1,2-dihydropyridin-1-yl)acetate
• CAS: 1508071-25-7
• 化学式: C₁₆H₂₅NO₆
• 分子量: 327.378
• InChiKey: BDEFUWWNIQQPHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.69
• 重原子数：
  23.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  75.99
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-[2-(2-methoxyethoxy)ethoxy]ethyl 2-(3,6-dimethyl-2-oxo-1,2-dihydropyridin-1-yl)acetate 在 氧气 、 tetraphenylporphyrin 、 sodium hydride 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1.5h， 生成 2-[2-(2-methoxyethoxy)ethoxy]ethyl 2-{1,4,8-trimethyl-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：

  2,5-二甲基吡啶 在 正丁基锂 、 1,3,5-三溴-1,3,5-噻嗪烷-2,4,6-三酮 、 硫酸 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 正己烷 、 水 为溶剂， 反应 8.33h， 生成 2-[2-(2-methoxyethoxy)ethoxy]ethyl 2-(3,6-dimethyl-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