3a-phenyl-2,3,3a,4-tetrahydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-1-one | 39484-92-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3a-phenyl-2,3,3a,4-tetrahydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-1-one
• 英文别名: 3a-phenyl-3,4-dihydro-2H-pyrrolo[1,2-a]benzimidazol-1-one
• CAS: 39484-92-9
• 化学式: C₁₆H₁₄N₂O
• 分子量: 250.3
• InChiKey: IIXONMQPWUMMAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3a-phenyl-2,3,3a,4-tetrahydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-1-one 在 硫酸 、 sodium nitrite 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以75%的产率得到7-nitroso-3a-phenyl-2,3,3a,4-tetrahydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-1-one
  参考文献：
  名称：

  Nitrosylation of 3a-substituted 2,3,3a,4-tetrahydro-1H-benzo[d]- pyrrolo[1,2-a]imidazol-1-ones

  摘要：

  DOI：

  10.1007/s10593-011-0790-4
• 作为产物：
  描述：

  邻苯二胺 、 3-苯丙烯溴酸酯 以 苯 为溶剂， 反应 5.0h， 以75%的产率得到3a-phenyl-2,3,3a,4-tetrahydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-1-one
  参考文献：
  名称：

  3a-Phenyl-2,3,3a,4-tetrahydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-1-one, a potential plant-growth regulator

  摘要：

  标题化合物 C16H14N2O 是一种潜在的植物生长调节剂，其分子通过分子间 C=O...H-N 氢键连接成链。这些链通过 π-π 堆叠作用微弱地相互连接，形成一个三维框架。本文比较了标题分子与几种相关苯并咪唑和吡咯烷酮的几何参数；

  DOI：

  10.1107/s0108270113016119

文献信息

• Electrophilic reactions as methods of modification of pyrrolobenzimidazolones and pyrroloquinazolinones
  作者：Vyacheslav S. Grinev、Alevtina Yu. Egorova

  DOI：10.1007/s10593-020-02751-z

  日期：2020.7

  The publication presents a number of modifications based on electrophilic reactions of previously synthesized biologically active benzannulated pyrrolo[1,2-a]imidazolones and pyrrolo[2,1-b]quinazolinones, which make it possible to widely change the physicochemical properties of molecules. Quantitative assessments of the lipophilicity of all synthesized compounds were carried out, on the basis of which

  该出版物提出了基于先前合成的具有生物活性的苯并环吡咯并[1,2-a]咪唑啉酮和吡咯并[2,1-b]喹唑啉酮的亲电反应的许多修饰，这些修饰使广泛改变分子的理化性质成为可能。对所有合成化合物的亲脂性进行了定量评估，在此基础上得出了有关引入烷基和三氟乙酰基以通过将其亲脂性提高至40％来提高化合物生物利用度的结论。
• Reaction of 4-oxocarboxylic acids and 5-substituted 3H-furan-2-ones with 1,2-binucleophiles of aromatic and alicyclic series
  作者：V. S. Grinev、O. A. Amal’chieva、A. Yu. Egorova、E. V. Lyubun’

  DOI：10.1134/s1070428010090198

  日期：2010.9

  Based on reactions of 5-substituted 3H-furan-2-ones or 4-oxocarboxylic acids with 1,2-binucleophiles of aromatic and aliphatic series methods were developed for the synthesis of tricyclic structures containing a pyrrolidine fragment fused with imidazolidine or oxazolidine ring. The pathways of the reactions are considered. It was demonstrated that the nature of the substrate did not affect the reaction direction, but changed the scheme of the interaction. The structures of compounds obtained for the first time were proved using IR and (1)H NMR spectra.
• Chimirri, Alba; Grasso, Silvana; Longeri, Marcello, Journal of Chemical Research, Miniprint, 1984, # 3, p. 601 - 618
  作者：Chimirri, Alba、Grasso, Silvana、Longeri, Marcello、Menniti, Giuseppa、Romeo, Giovanni、Valle, Giovanni

  DOI：——

  日期：——
• Separation of the enantiomers of anticonvulsant tricyclic pyrroloimidazolones by enantioselective HPLC. A chiral recognition model and a chiroptical study
  作者：Salvatore Caccamese、Grazia Principato、Alba Chimirri、Silvana Grasso

  DOI：10.1016/0957-4166(96)00331-x

  日期：1996.9

  The enantiomers of several pyrrolobenzimidazolone and pyrroloimidazopyridine derivatives have been successfully resolved by HPLC on a Whelk-O 1 Chiral Stationary Phase superior to other CSPs. A chiral recognition model explained the substituent effects on the enantioselectivity and afforded correlation of the elution order of the enantiomers to their absolute configuration. The exciton coupling method was applied to the CD spectra of the isolated enantiomers to confirm their absolute configuration. Copyright (C) 1996 Published by Elsevier Science Ltd
• 3a-Phenyl-2,3,3a,4-tetrahydro-1<i>H</i>-benzo[<i>d</i>]pyrrolo[1,2-<i>a</i>]imidazol-1-one, a potential plant-growth regulator
  作者：Vyacheslav S. Grinev、Alevtina Yu. Egorova

  DOI：10.1107/s0108270113016119

  日期：2013.8.15

  Molecules of the title compound, C₁₆H₁₄N₂O, a potential plant-growth regulator, are linked into chains by intermolecular C=O...H—N hydrogen bonds. These chains are weakly interconnected by π–π stacking interactions to form a three-dimensional framework. A comparison of the geometric parameters of the title molecule and several related benzimidazoles and pyrrolidones is presented.<!?tpb=22pt>

  标题化合物 C16H14N2O 是一种潜在的植物生长调节剂，其分子通过分子间 C=O...H-N 氢键连接成链。这些链通过 π-π 堆叠作用微弱地相互连接，形成一个三维框架。本文比较了标题分子与几种相关苯并咪唑和吡咯烷酮的几何参数；