3-[6-(2-Chlorocarbonyl-ethyl)-1,3,5,7-tetraoxo-3,5,6,7-tetrahydro-1H-pyrrolo[3,4-f]isoindol-2-yl]-propionyl chloride | 128007-80-7

• 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: 3-[6-(2-Chlorocarbonyl-ethyl)-1,3,5,7-tetraoxo-3,5,6,7-tetrahydro-1H-pyrrolo[3,4-f]isoindol-2-yl]-propionyl chloride
• CAS: 128007-80-7
• 化学式: C₁₆H₁₀Cl₂N₂O₆
• 分子量: 397.171
• InChiKey: MHMTZXXZBXNFMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.22
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  112.28
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxyethyl)-3-(6-nonyl-4-oxo-1,4-dihydropyrimidin-2-yl)urea 、 3-[6-(2-Chlorocarbonyl-ethyl)-1,3,5,7-tetraoxo-3,5,6,7-tetrahydro-1H-pyrrolo[3,4-f]isoindol-2-yl]-propionyl chloride 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 10.0h， 以80 mg的产率得到
  参考文献：
  名称：

  Donor–acceptor interaction-mediated arrangement of hydrogen bonded dimers

  摘要：

  The donor-acceptor interaction-driven supramolecular arrangement of a new series of quadruply hydrogen-bonded homo- and heterodimers have been investigated in chloroform with H-1 NMR and UV-Vis spectroscopy. Two kinds of structurally complementary monomers have been prepared. Monomers 3 and 4 are incorporated with one ureidopyrimidone unit and one electron deficient pyromellitic diimide (PDI) or naphthalene diimide (NDI) unit, respectively, monomers 5 and 6 are incorporated with two ureidopyrimidone units and one PDI or NDI unit, respectively, whereas monomers 7 and 8 consist of one electron rich bis-p-phenylene[34]crown-10 unit and one or two 2,7-diamido-1,6-naphthyridine units, respectively. Compounds 3 and 4 exist exclusively as homodimers, respectively. Adding 1 equiv. of 7 to the solution of 3.3 and 4.4 induced them to partially or fully dissociate to produce heterodimers 3.7 and 4.7 due to intermolecular donor-acceptor interaction and the formation of a new binding mode between the ureidopyrimidone of 3 or 4 and the 2,7-diamido-1,6-naphthyridine unit of 7. Both 5 and 6 exist as cyclic monomer and dimer in chloroform. Adding 1 equiv. of 8 to the solution of 5 or 6 in chloroform caused all the cyclic dimer and most of the cyclic monomer to de-cyclize to form new heterodimers 5.8 and 6.8, respectively. H-1 NMR and UV-vis study revealed that heterodimer 5.8 has a structure in which the PDI of 5 is not threaded through the cavity of the bis-p-phenylene [34] crown-10 unit of 8. In contrast, in addition to the heterodimer similar to 5.8, about 40% of heterodimer 6.8 is generated, in which the PDI of 6 is threaded through the cavity of the bis-p-phenylene[3]crown-10 unit of 8 due to the increased donor-acceptor interaction between NDI and bis-p-phenylene [34] crown-10. Steric hindrance and mismatching of the hydrogen bonding moiety play important roles in the arrangement of the new homo- and heterodimers. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.104
• 作为产物：
  描述：

  均苯四甲酸二酐 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 3-[6-(2-Chlorocarbonyl-ethyl)-1,3,5,7-tetraoxo-3,5,6,7-tetrahydro-1H-pyrrolo[3,4-f]isoindol-2-yl]-propionyl chloride
  参考文献：
  名称：

  Donor–acceptor interaction-mediated arrangement of hydrogen bonded dimers

  摘要：

  The donor-acceptor interaction-driven supramolecular arrangement of a new series of quadruply hydrogen-bonded homo- and heterodimers have been investigated in chloroform with H-1 NMR and UV-Vis spectroscopy. Two kinds of structurally complementary monomers have been prepared. Monomers 3 and 4 are incorporated with one ureidopyrimidone unit and one electron deficient pyromellitic diimide (PDI) or naphthalene diimide (NDI) unit, respectively, monomers 5 and 6 are incorporated with two ureidopyrimidone units and one PDI or NDI unit, respectively, whereas monomers 7 and 8 consist of one electron rich bis-p-phenylene[34]crown-10 unit and one or two 2,7-diamido-1,6-naphthyridine units, respectively. Compounds 3 and 4 exist exclusively as homodimers, respectively. Adding 1 equiv. of 7 to the solution of 3.3 and 4.4 induced them to partially or fully dissociate to produce heterodimers 3.7 and 4.7 due to intermolecular donor-acceptor interaction and the formation of a new binding mode between the ureidopyrimidone of 3 or 4 and the 2,7-diamido-1,6-naphthyridine unit of 7. Both 5 and 6 exist as cyclic monomer and dimer in chloroform. Adding 1 equiv. of 8 to the solution of 5 or 6 in chloroform caused all the cyclic dimer and most of the cyclic monomer to de-cyclize to form new heterodimers 5.8 and 6.8, respectively. H-1 NMR and UV-vis study revealed that heterodimer 5.8 has a structure in which the PDI of 5 is not threaded through the cavity of the bis-p-phenylene [34] crown-10 unit of 8. In contrast, in addition to the heterodimer similar to 5.8, about 40% of heterodimer 6.8 is generated, in which the PDI of 6 is threaded through the cavity of the bis-p-phenylene[3]crown-10 unit of 8 due to the increased donor-acceptor interaction between NDI and bis-p-phenylene [34] crown-10. Steric hindrance and mismatching of the hydrogen bonding moiety play important roles in the arrangement of the new homo- and heterodimers. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.104