exo-3,6-dimethyl-3,6-epoxy-1,2,3,6-tetrahydrophthalimide | 1189948-66-0

• 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: exo-3,6-dimethyl-3,6-epoxy-1,2,3,6-tetrahydrophthalimide
• 英文别名: (3aR,4S,7R,7aS)-4,7-dimethyl-3a,7a-dihydro-4,7-epoxyisoindole-1,3-dione
• CAS: 1189948-66-0
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: CIUXLATYFJJJIP-YUMGAWCOSA-N

物化性质

• 熔点：
  119-121 °C
• 沸点：
  357.3±42.0 °C(Predicted)
• 密度：
  1.357±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,5-二甲基呋喃 、 马来酰亚胺 以 乙腈 为溶剂， 以60%的产率得到
  参考文献：
  名称：

  Protected Maleimide Building Blocks for the Decoration of Peptides, Peptoids, and Peptide Nucleic Acids

  摘要：

  Monomers allowing for the introduction of [2,5-dimethylfuran]-protected maleimides into polyamides such as peptides, peptide nucleic acids, and peptoids were prepared, as well as the corresponding oligomers. Suitable maleimide deprotection conditions were established in each case. The stability of the adducts generated by Michael-type maleimide-thiol reaction and Diels-Alder cycloaddition to maleimide deprotection conditions was exploited to prepare a variety of conjugates from peptide and PNA scaffolds incorporating one free and one protected maleimide. The target molecules were synthesized by using two subsequent maleimide-involving click reactions separated by a maleimide deprotection step. Carrying out maleimide deprotection and conjugation simultaneously gave better results than performing the two reactions subsequently.

  DOI：

  10.1021/bc4000614

文献信息

• SYNTESIS AND CRYSTALLINE STRUCTURE OF THE EXO-3,6-DIMETHYL-3,6-EPOXI-1,2,3,6-TETRAHYDROPHTLALIMIDE AND ITS N-BROMODECYL ANALOG: TWO THERMALLY LABILE DIELS-ALDER ADDUCTS
  作者：RODRIGO VÁSQUEZ、CLAUDIA VETTERLEIN、ALEXANDER TRUJILLO、CARLOSA ESCOBAR、EYLEEN ARAYA-FUENTES

  DOI：10.4067/s0717-97072014000200016

  日期：——
• Protected Maleimide Building Blocks for the Decoration of Peptides, Peptoids, and Peptide Nucleic Acids
  作者：Xavier Elduque、Albert Sánchez、Kapil Sharma、Enrique Pedroso、Anna Grandas

  DOI：10.1021/bc4000614

  日期：2013.5.15

  Monomers allowing for the introduction of [2,5-dimethylfuran]-protected maleimides into polyamides such as peptides, peptide nucleic acids, and peptoids were prepared, as well as the corresponding oligomers. Suitable maleimide deprotection conditions were established in each case. The stability of the adducts generated by Michael-type maleimide-thiol reaction and Diels-Alder cycloaddition to maleimide deprotection conditions was exploited to prepare a variety of conjugates from peptide and PNA scaffolds incorporating one free and one protected maleimide. The target molecules were synthesized by using two subsequent maleimide-involving click reactions separated by a maleimide deprotection step. Carrying out maleimide deprotection and conjugation simultaneously gave better results than performing the two reactions subsequently.