isopropyl dl-2-bromo-4-(N-phthalimido)butanoate | 130755-76-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: isopropyl dl-2-bromo-4-(N-phthalimido)butanoate
• 英文别名: Isopropyl 2-bromo-4-(1,3-dioxoisoindolin-2-yl)butanoate；propan-2-yl 2-bromo-4-(1,3-dioxoisoindol-2-yl)butanoate
• CAS: 130755-76-9
• 化学式: C₁₅H₁₆BrNO₄
• 分子量: 354.2
• InChiKey: LLBGGTDJNGEUJJ-UHFFFAOYSA-N

物化性质

• 沸点：
  440.6±35.0 °C(Predicted)
• 密度：
  1.475±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  轮环藤宁 、 isopropyl dl-2-bromo-4-(N-phthalimido)butanoate 以 氯仿 为溶剂， 以81%的产率得到1,4,7,10-tetraaza-1-N-(1-carboisopropoxy-3-(N-phthalimido)propyl)cyclododecane hydrobromide
  参考文献：
  名称：

  Unexpected selectivity in the alkylation of polyazamacrocycles

  摘要：

  Reaction of equivalent amounts of free base polyazamacrocycles with an alkyl halide in a nonpolar, aprotic solvent affords the mono-N-alkylation product as its monohydrohalide salt in high yield with excellent selectivity. This unexpected selectivity has been explained in terms of the high affinity of the alkylated product for a single proton which attenuates the nucleophilicity of the remaining nitrogen atoms. Selectivity is dependent upon a number of factors including macrocycle ring size, solvent polarity, and the steric nature of the electrophile. The approach has allowed for a short, convergent route to bifunctional lanthanide chelators which are useful in therapeutic applications.

  DOI：

  10.1021/jo00067a018
• 作为产物：
  描述：

  苯酐 、 alkaline earth salt of/the/ methylsulfuric acid 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 1.5h， 生成 isopropyl dl-2-bromo-4-(N-phthalimido)butanoate
  参考文献：
  名称：

  Unexpected selectivity in the alkylation of polyazamacrocycles

  摘要：

  Reaction of equivalent amounts of free base polyazamacrocycles with an alkyl halide in a nonpolar, aprotic solvent affords the mono-N-alkylation product as its monohydrohalide salt in high yield with excellent selectivity. This unexpected selectivity has been explained in terms of the high affinity of the alkylated product for a single proton which attenuates the nucleophilicity of the remaining nitrogen atoms. Selectivity is dependent upon a number of factors including macrocycle ring size, solvent polarity, and the steric nature of the electrophile. The approach has allowed for a short, convergent route to bifunctional lanthanide chelators which are useful in therapeutic applications.

  DOI：

  10.1021/jo00067a018