2,3-Dihydro-5H-pyrrolo<1,2-a>isoindole-2,5-dione | 108159-82-6

• 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: 2,3-Dihydro-5H-pyrrolo<1,2-a>isoindole-2,5-dione
• 英文别名: 3H-pyrrolo[2,1-a]isoindole-2,5-dione；2H-pyrrolo[2,1-a]isoindole-2,5(3H)dione；3H-pyrrolo[1,2-b]isoindole-2,5-dione
• CAS: 108159-82-6
• 化学式: C₁₁H₇NO₂
• 分子量: 185.182
• InChiKey: WWAIIMGUTYSQSW-UHFFFAOYSA-N

物化性质

• 熔点：
  190-193 °C
• 沸点：
  422.4±45.0 °C(predicted)
• 密度：
  1.44±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丙烯酰碘 、 2,3-Dihydro-5H-pyrrolo<1,2-a>isoindole-2,5-dione 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以86%的产率得到3-allyl-2H-pyrrolo[2,1-a]isoindole-2,5(3H)dione
  参考文献：
  名称：

  Efficient Horner–Wadsworth–Emmons intramolecular cyclisation of a N-substituted phthalimide promoted by KF-Alumina: a general tool for the synthesis of functionalised isoindolinones

  摘要：

  An intramolecular Horner-Wadsworth-Emmons reaction promoted by KF-Alumina involving a N-substituted phthalimide, cleanly and efficiently furnishes an interesting alpha,beta-unsaturated tricyclic enone which may undergo selective alkylations at the alpha'-position. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.04.029
• 作为产物：
  描述：

  邻苯二甲酰甘氨酸 在 乙醇 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 16.5h， 生成 2,3-Dihydro-5H-pyrrolo<1,2-a>isoindole-2,5-dione
  参考文献：
  名称：

  Synthesis of Pyrrolizidinediones from CyclicN,N-Diacylamino Acids

  摘要：

  环状 N,N-二乙酰基氨基酸可通过与 N-苯基乙烯亚氨基三苯基膦反应转化为吡咯烷二酮。

  DOI：

  10.1246/cl.1986.1527

文献信息

• 1-Phthalimido-4-(3-indolyl)-2-siloxy-1,3-butadienes: synthesis and Diels–Alder reactivity
  作者：Esther Caballero、Dulce Alonso、Rafael Peláez、Concepción Alvarez、Pilar Puebla、Francisca Sanz、Manuel Medarde、Fernando Tomé

  DOI：10.1016/j.tetlet.2003.12.118

  日期：2004.2

  New 1-phthalimido-4-(3-indolyl)-2-trialkylsiloxy-1,3-butadienes were easily prepared from 1,3-dichloropropanone and their configurations were established from NMR data. Their Diels–Alder reactivity with different maleimides and quinones was studied, high yields of the exo cycloadducts being obtained, as confirmed by X-ray diffraction studies.

  新的1-邻苯二甲酰亚胺-4-（3-吲哚基）-2-三烷基甲硅烷氧基-1,3-丁二烯很容易从1,3-二氯丙烷制得，其构型由NMR数据确定。研究了它们与不同的马来酰亚胺和醌的Diels-Alder反应性，通过X射线衍射研究证实，该化合物可得到高产率的exo环加合物。
• Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 7. Cyclisation of amino acid derived α-phtnalimidoacyl ylides to give pyrroloisoindolediones
  作者：R. Alan Aitken、Harris R. Cooper、Amit P. Mehrotra

  DOI：10.1039/p19960000475

  日期：——

  A series of 11 amino acid-derived stabilised ylides 12-14 and 16 have been prepared and characterised. In one case, for compound 17, an X-ray structure determination supports formulation of the compounds as phosphonium enolates. Flash vacuum pyrolysis (FVP) of 12 and 13 at 500 degrees C results ih loss of R(3)(2)PO between the ylide function and one carbonyl of the phthalimido group to give products characterised spectroscopically as the pyrroloisoindolediones 18. The identity of these is also supported by the results of C-13 and N-15 labelling experiments, but owing to their high reactivity complete separation from the phosphine oxide was not generally possible even when Bu(3)PO rather than Ph(3)PO was involved. Chromatographic purification of 29, similarly produced by FVP of 14, led to partial hydrolysis, rearrangement and decarboxylation to give 30. FVP of 12 at 750 degrees C gave the 1-unsubstituted pyrroloisoindolediones 19 in two cases.
• Ionic liquid-catalyzed and microwave-assisted syntheses of pyrrolizine- and indolizinedione derivatives
  作者：I. M. Sakhautdinov、I. R. Batyrshin、N. A. Sergeeva、F. Z. Galin、M. S. Yunusov

  DOI：10.1134/s1070428012060073

  日期：2012.6

  3H-Pyrrolo[2,1-a]isoindole-2,5-diones and isoindolo[2,1-a]quinoline-5,11-diones were synthesized by intramolecular cyclization of N-[2-oxo-3-(triphenyl-lambda(5)-phosphanylidene)propyl]- and N-[2-(triphenyl-lambda(5)-phosphanylidene)acetyl]phthalimides, respectively, in the presence of ionic liquid ([bmim][BF4], 10 mol %) as catalyst or under microwave irradiation.
• BESTMANN H. J.; MOENIUS TH.; SOLIMAN F., CHEM. LETT.,(1986) N 9, 1527-1528
  作者：BESTMANN H. J.、 MOENIUS TH.、 SOLIMAN F.

  DOI：——

  日期：——
• Efficient Horner–Wadsworth–Emmons intramolecular cyclisation of a N-substituted phthalimide promoted by KF-Alumina: a general tool for the synthesis of functionalised isoindolinones
  作者：Vittorio Pace、Fernando Martínez、Clara I. Nova、María Fernández、José Vicente Sinisterra、Andrés R. Alcántara

  DOI：10.1016/j.tetlet.2009.04.029

  日期：2009.6

  An intramolecular Horner-Wadsworth-Emmons reaction promoted by KF-Alumina involving a N-substituted phthalimide, cleanly and efficiently furnishes an interesting alpha,beta-unsaturated tricyclic enone which may undergo selective alkylations at the alpha'-position. (C) 2009 Elsevier Ltd. All rights reserved.