2,6-di-prop-2-ynyl-pyrrolo[3,4-f]isoindole-1,3,5,7-tetraone | 18158-82-2

• 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: 2,6-di-prop-2-ynyl-pyrrolo[3,4-f]isoindole-1,3,5,7-tetraone
• 英文别名: 2,6-Bis(prop-2-ynyl)pyrrolo[3,4-f]isoindole-1,3,5,7-tetrone
• CAS: 18158-82-2
• 化学式: C₁₆H₈N₂O₄
• 分子量: 292.251
• InChiKey: CNTWHCWLYBRQKW-UHFFFAOYSA-N

物化性质

• 熔点：
  >360 °C(Solv: acetone (67-64-1))
• 沸点：
  493.1±40.0 °C(Predicted)
• 密度：
  1.526±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1(1,5)-naphthalena 15(1,3)-(5-carboxybenzena)-2,5,8,11,14,16,19,22,25,28-decaoxacyclo-octacosaphane 、 2,6-di-prop-2-ynyl-pyrrolo[3,4-f]isoindole-1,3,5,7-tetraone 在 copper(l) chloride 、 copper dichloride 作用下， 以 N,N-二甲基甲酰胺 、 甲醇 为溶剂， 反应 48.5h， 以20%的产率得到
  参考文献：
  名称：

  Sn(IV) Porphyrins as NMR Shift Reagents and Supramolecular Protecting Groups:  Preparation of a Carboxylate−Catenane Porphyrin Complex

  摘要：

  Coordination of a carboxylic acid diaryl crown ether to a Sn(IV) porphyrin promotes its ability to act as a template for the formation of a [2]catenane: in the absence of the porphyrin the acid-crown yields only a tiny amount of the interlocked derivative, Once isolated the free acid-[2]catenane presents extremely broad resonances in its 500 MHz H-1 NMR spectrum, but complexation to a Sn(IV) porphyrin results in dramatic resolution via a combination of dynamic and dispersive effects.

  DOI：

  10.1021/ol990891j
• 作为产物：
  描述：

  均苯四甲酸二酐 、 炔丙胺 以 N,N-二甲基甲酰胺 为溶剂， 以28%的产率得到2,6-di-prop-2-ynyl-pyrrolo[3,4-f]isoindole-1,3,5,7-tetraone
  参考文献：
  名称：

  Synthesis, Structure and Photophysics of Neutral π-Associated [2]Catenanes

  摘要：

  The supramolecular utility of a neutral re-stacking system of aromatic donors and accepters is illustrated with the syntheses of three neutral [2]catenanes. These templated syntheses are based on the oxidative dimerisation of electron-deficient aromatic diimide derivatives, equipped with terminal acetylene functions, in the presence of a preformed crown macrocycle containing complementary electron-rich aromatic diethers. X-ray crystallographic study of one of the catenanes and a precatenane crown/diimide inclusion complex reveals the ordered donor-acceptor stacking responsible for templating the catenane syntheses and subsequently organising the packing of the interlocked molecules in the solid state. NMR investigation of the catenanes reveals a dominant dynamic process at room temperature involving the sweeping of the crown macrocycle around the periphery of the interlocked structures; NOESY exchange spectra reveal a higher-energy process involving the revolution of the crown macrocycle through the centre of the second ring. This combined dynamic picture has been used to support the observed photophysical behaviour. Room-temperature fluorescence of the catenanes is only partially quenched by neighbouring chromophores, implying some mobility in the constituent rings; for one of the catenanes fluorescence quenching data enables an estimate to be made of the ratio of translational isomers present in solution. In contrast, low-temperature (77 K) fluorescence is totally quenched as a consequence of freezing all dynamic movement. Collectively, the results presented in this work lend support to the assertion that the robust, neutral building blocks employed in the catenane syntheses are ideal vehicles for the development of complex [n]catenane syntheses.

  DOI：

  10.1002/(sici)1521-3765(19980416)4:4<608::aid-chem608>3.0.co;2-c

文献信息

• Neutral [2]catenanes from oxidative coupling of π-stacked components
  作者：Darren G. Hamilton、Jeremy K. M. Sanders、John E. Davies、William Clegg、Simon J. Teat

  DOI：10.1039/a701048f

  日期：——

  Oxidative dimerisation of bis-acetylenic precursors in the presence of a dinaphtho-crown ether affords neutral [2]catenanes in good yields; the interaction of the complementary donor–acceptor π-systems ensures assembly in a geometry favouring catenane formation.

  在二萘冠醚存在下，双炔烃前体的氧化二聚反应可生成中性[2]链烷，且收率较高；互补供体-受体Β-系统的相互作用可确保在有利于链烷形成的几何结构中进行组装。
• Hamilton, Darren G.; Prodi, Luca; Feeder, Neil, Journal of the Chemical Society. Perkin transactions I, 1999, # 8, p. 1057 - 1065
  作者：Hamilton, Darren G.、Prodi, Luca、Feeder, Neil、Sanders, Jeremy K. M.

  DOI：——

  日期：——
• Eldeen; Cosmo; Ghantous, European Journal of Medicinal Chemistry, 1981, vol. 16, # 1, p. 91 - 93
  作者：Eldeen、Cosmo、Ghantous、Khayat

  DOI：——

  日期：——
• Tandem Hetero-Catenation:  Templating and Self-Assembly in the Mutual Closure of Two Different Interlocking Rings
  作者：Darren G. Hamilton、Neil Feeder、Luca Prodi、Simon J. Teat、William Clegg、Jeremy K. M. Sanders

  DOI：10.1021/ja9731884

  日期：1998.2.1
• ELDEEN Z. M.; COSMO A. N.; GHANTOUS H.; KHAYAT A., EUR. J. MED. CHEM.-CHIM. THER., 1981, 16, NO 1,91-93
  作者：ELDEEN Z. M.、 COSMO A. N.、 GHANTOUS H.、 KHAYAT A.

  DOI：——

  日期：——