3-(1-{8-[4-(2-ethoxycarbonyl-ethyl)-2,5-dioxo-imidazolidin-1-yl]-octyl}-2,5-dioxoimidazolidin-4-yl)-propionic acid ethyl ester | 892495-96-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3-(1-{8-[4-(2-ethoxycarbonyl-ethyl)-2,5-dioxo-imidazolidin-1-yl]-octyl}-2,5-dioxoimidazolidin-4-yl)-propionic acid ethyl ester
• 英文别名: Ethyl 3-[1-[8-[4-(3-ethoxy-3-oxopropyl)-2,5-dioxoimidazolidin-1-yl]octyl]-2,5-dioxoimidazolidin-4-yl]propanoate
• CAS: 892495-96-4
• 化学式: C₂₄H₃₈N₄O₈
• 分子量: 510.588
• InChiKey: QTFIHNDTXSWJCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  36
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  151
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-(1-{8-[4-(2-ethoxycarbonyl-ethyl)-2,5-dioxo-imidazolidin-1-yl]-octyl}-2,5-dioxoimidazolidin-4-yl)-propionic acid ethyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 16.0h， 生成 10,21,25,26-tetraoxo-1,6,11,20-tetraaza-tricyclo[18.4.1.1^6,11]hexacosane-7,24-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Synthesis of N(3),N‘(3)-Polymethylene-bis-hydantoins and Their Macrocyclic Derivatives

  摘要：

  An efficient and straightforward two-step approach toward N(3), N'(3)-polymethylene-bis-hydantoins was developed. As a first step, a pyroglutamate is reacted with a diisocyanate to produce a bis-carbamoyllactam. The second step is a double-ring transformation by treatment of this bis-carbamoyllactam with KOtBu in ethanol. In this fashion N(3), N'(3)-polymethylene-bis-hydantoins are produced in two quantitative steps and under very mild conditions. When properly derivatized, these compounds can be converted to their macrocyclic derivatives upon treatment with 5 mol % of second-generation Grubbs' catalyst. These macrocyclic derivatives are so far not described in the literature. It was proven that exclusively (E)-isomers are formed.

  DOI：

  10.1021/jo060370r
• 作为产物：
  描述：

  ethyl 1-({[8-({[2-(ethoxycarbonyl)-5-oxopyrrolidin-1-yl]-carbonyl}amino)octyl]amino}carbonyl)-5-oxopyrrolidine-2-carboxylate 在 potassium tert-butylate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以99%的产率得到3-(1-{8-[4-(2-ethoxycarbonyl-ethyl)-2,5-dioxo-imidazolidin-1-yl]-octyl}-2,5-dioxoimidazolidin-4-yl)-propionic acid ethyl ester
  参考文献：
  名称：

  Synthesis of N(3),N‘(3)-Polymethylene-bis-hydantoins and Their Macrocyclic Derivatives

  摘要：

  An efficient and straightforward two-step approach toward N(3), N'(3)-polymethylene-bis-hydantoins was developed. As a first step, a pyroglutamate is reacted with a diisocyanate to produce a bis-carbamoyllactam. The second step is a double-ring transformation by treatment of this bis-carbamoyllactam with KOtBu in ethanol. In this fashion N(3), N'(3)-polymethylene-bis-hydantoins are produced in two quantitative steps and under very mild conditions. When properly derivatized, these compounds can be converted to their macrocyclic derivatives upon treatment with 5 mol % of second-generation Grubbs' catalyst. These macrocyclic derivatives are so far not described in the literature. It was proven that exclusively (E)-isomers are formed.

  DOI：

  10.1021/jo060370r