3,3'-(1,3,5,7-tetraoxo-5,7-dihydro-1H,3H-pyrrolo[3,4-f]isoindole-2,6-diyl)-bis-propionic acid | 14027-94-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3,3'-(1,3,5,7-tetraoxo-5,7-dihydro-1H,3H-pyrrolo[3,4-f]isoindole-2,6-diyl)-bis-propionic acid
• 英文别名: 3,3'-(1,3,5,7-tetraoxo-5,7-dihydropyrrolo[3,4-f]isoindole-2,6(1H,3H)-diyl)dipropionic acid；3,3'-(1,3,5,7-tetraoxo-5,7-dihydro-1H,3H-pyrrolo[3,4-f]isoindole-2,6-diyl)-bis-propionic acid；N,N'-Bis-<2-carboxy-ethyl>-pyromellithsaeure-diimid；Cambridge id 5754491；3-[2-(2-carboxyethyl)-1,3,5,7-tetraoxopyrrolo[3,4-f]isoindol-6-yl]propanoic acid
• CAS: 14027-94-2
• 化学式: C₁₆H₁₂N₂O₈
• mdl: MFCD01162829
• 分子量: 360.28
• InChiKey: IOZZQVJPSHEBFG-UHFFFAOYSA-N

物化性质

• 熔点：
  329-330 °C
• 沸点：
  699.1±50.0 °C(Predicted)
• 密度：
  1.690±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  149
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,3'-(1,3,5,7-tetraoxo-5,7-dihydro-1H,3H-pyrrolo[3,4-f]isoindole-2,6-diyl)-bis-propionic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 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
• 作为产物：
  描述：

  均苯四甲酸二酐 、 β-丙氨酸 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以87.3%的产率得到3,3'-(1,3,5,7-tetraoxo-5,7-dihydro-1H,3H-pyrrolo[3,4-f]isoindole-2,6-diyl)-bis-propionic acid
  参考文献：
  名称：

  基于酰胺羧酸的“S”形有机锡（IV）羧酸盐：合成、晶体结构和抗肿瘤活性

  摘要：

  摘要 基于酰胺羧酸的三种有机锡羧酸盐：(Ph3Sn)2(L1) (1) (L1 = 3,3'-(1,3,5,7-tetraoxo-5,7-dihydropyrrolo[3,4-f ]isoindole-2,6(1H,3H)-diyl)dipropionic acid), (Ph3Sn)2(L2)·C7H8 (2) (L2 = 3,3'-(1,3,6,8-tetraoxo-1) ,3,6,8-四氢苯并 [lmn][3,8]phenanthroline-2,7-diyl)dipropionic acid), [(Ph3Sn)(CH3CH2O)]2(L3) (3) (L3 = 2,2' -(1,3,5,7-tetraoxo-5,7-dihydropyrrolo[3,4-f]isoindole-2,6(1H,3H)-diyl) dibenzoic acid) 合成并通过元素分析、IR、 1H、13C、119Sn

  DOI：

  10.1016/j.molstruc.2016.10.083

文献信息

• Donor–acceptor interaction-mediated arrangement of hydrogen bonded dimers
  作者：Xiao-Qiang Li、Dai-Jun Feng、Xi-Kui Jiang、Zhan-Ting Li

  DOI：10.1016/j.tet.2004.06.104

  日期：2004.9

  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.
• “S” shaped organotin(IV) carboxylates based on amide carboxylic acids: Syntheses, crystal structures and antitumor activities
  作者：Xiao Xiao、Yan Li、Yuan Dong、Wenliang Li、Kun Xu、Nianqiu Shi、Xin Liu、Jingyi Xie、Peigen Liu

  DOI：10.1016/j.molstruc.2016.10.083

  日期：2017.2

  Abstract Three organotin carboxylates based on amide carboxylic acids: (Ph3Sn)2(L1) (1) (L1 = 3,3′-(1,3,5,7-tetraoxo-5,7-dihydropyrrolo[3,4-f]isoindole-2,6(1H,3H)-diyl)dipropionic acid), (Ph3Sn)2(L2)·C7H8 (2) (L2 = 3,3′-(1,3,6,8-tetraoxo-1,3,6,8-tetrahydrobenzo [lmn][3,8]phenanthroline-2,7-diyl)dipropionic acid), [(Ph3Sn)(CH3CH2O)]2(L3) (3) (L3 = 2,2′-(1,3,5,7-tetraoxo-5,7-dihydropyrrolo[3,4-f]isoindole-2

  摘要 基于酰胺羧酸的三种有机锡羧酸盐：(Ph3Sn)2(L1) (1) (L1 = 3,3'-(1,3,5,7-tetraoxo-5,7-dihydropyrrolo[3,4-f ]isoindole-2,6(1H,3H)-diyl)dipropionic acid), (Ph3Sn)2(L2)·C7H8 (2) (L2 = 3,3'-(1,3,6,8-tetraoxo-1) ,3,6,8-四氢苯并 [lmn][3,8]phenanthroline-2,7-diyl)dipropionic acid), [(Ph3Sn)(CH3CH2O)]2(L3) (3) (L3 = 2,2' -(1,3,5,7-tetraoxo-5,7-dihydropyrrolo[3,4-f]isoindole-2,6(1H,3H)-diyl) dibenzoic acid) 合成并通过元素分析、IR、 1H、13C、119Sn