3-(1-{12-[4-(2-ethoxycarbonyl-ethyl)-2,5-dioxo-imidazolidin-1-yl]-dodecyl}-2,5-dioxoimidazolidin-4-yl)-propionic acid ethyl ester | 892495-97-5

• 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-{12-[4-(2-ethoxycarbonyl-ethyl)-2,5-dioxo-imidazolidin-1-yl]-dodecyl}-2,5-dioxoimidazolidin-4-yl)-propionic acid ethyl ester
• 英文别名: Ethyl 3-[1-[12-[4-(3-ethoxy-3-oxopropyl)-2,5-dioxoimidazolidin-1-yl]dodecyl]-2,5-dioxoimidazolidin-4-yl]propanoate
• CAS: 892495-97-5
• 化学式: C₂₈H₄₆N₄O₈
• 分子量: 566.695
• InChiKey: QZXZYSMSSMMBAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  40
• 可旋转键数：
  23
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 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-{12-[4-(2-ethoxycarbonyl-ethyl)-2,5-dioxo-imidazolidin-1-yl]-dodecyl}-2,5-dioxoimidazolidin-4-yl)-propionic acid ethyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 3-[24-(2-ethoxycarbonyl-ethyl)-8,23,25,26-tetraoxo-1,6,9,22-tetraaza-tricyclo[20.2.1.1^6,9]hexacos-3-en-7-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
• 作为产物：
  描述：

  ethyl 1-({[12-({[2-(ethoxycarbonyl)-5-oxopyrrolidin-1-yl]-carbonyl}amino)dodecyl]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-{12-[4-(2-ethoxycarbonyl-ethyl)-2,5-dioxo-imidazolidin-1-yl]-dodecyl}-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