2-phenyl-1H-benzo[e]isoindole-1,3(2H)-dione | 130728-71-1

• 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-phenyl-1H-benzo[e]isoindole-1,3(2H)-dione
• 英文别名: N-Phenyl-1,2-naphthalimide；2-phenylbenzo[e]isoindole-1,3-dione
• CAS: 130728-71-1
• 化学式: C₁₈H₁₁NO₂
• 分子量: 273.291
• InChiKey: LXFZGJFSGQMKJP-UHFFFAOYSA-N

物化性质

• 熔点：
  162-163 °C
• 沸点：
  482.8±28.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 palladium on activated charcoal 、 苯 作用下， 生成 2-phenyl-1H-benzo[e]isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Condensed Cyclobutane Aromatic Compounds. VII. Diels-Alder Adducts of Benzocyclobutadiene

  摘要：

  DOI：

  10.1021/ja01529a039

文献信息

• SMMR (small molecule metabolite reporters) for use as in vivo glucose biosensors
  申请人：Bellott M. Emile

  公开号：US20070110672A1

  公开（公告）日：2007-05-17

  Small Molecule Metabolite Reporters (SMMRs) for use as in vivo glucose biosensors, sensor compositions, and methods of use, are described. The SMMRs include boronic acid-containing xanthene, coumarin, carbostyril and phenalene-based small molecules which are used for monitoring glucose in vivo, advantageously on the skin.

  用于体内葡萄糖生物传感器的Small Molecule Metabolite Reporters (SMMRs)、传感器组合物及其使用方法被描述。SMMRs包括含有硼酸的小分子，基于黄烷、香豆素、卡波罗司坦和菲内烯，用于监测体内的葡萄糖，优选在皮肤上。
• A Rhodium-Catalyzed Cascade Cyclization: Direct Synthesis of<i>N</i>-Substituted Phthalimides from Isocyanates and Benzoic Acids
  作者：Xian-Ying Shi、Andrea Renzetti、Soumen Kundu、Chao-Jun Li

  DOI：10.1002/adsc.201300834

  日期：2014.3.10

  A rhodium(III)‐catalyzed amidation between benzoic acids and isocyanates via direct functionalization of an ortho CH bond followed by intramolecular cyclization is described. This cascade cyclization affords N‐substituted phthalimides in one step in 26–91% yields. The reaction is highly atom‐economical, since no theoretical waste except for water is generated in the reaction.

  苯甲酸和异氰酸酯之间的铑（III）催化的酰胺化通过一个的直接官能邻Ç  H键，随后分子内环化进行说明。这种级联环化一步即可提供N取代的邻苯二甲酰亚胺，产率为26-91％。该反应是高度原子经济的，因为在反应中除水外没有产生理论上的浪费。
• Carbonylation Access to Phthalimides Using Self-Sufficient Directing Group and Nucleophile
  作者：Fanghua Ji、Jianxiao Li、Xianwei Li、Wei Guo、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/acs.joc.7b02433

  日期：2018.1.5

  Herein we report a novel palladium-catalyzed oxidative carbonylation reaction for the synthesis of phthalimides with high atom- and step-economy. In our strategy, the imine and H2O, which are generated in situ from the condensation of aldehyde and amine, serve as self-sufficient directing group and nucleophile, respectively. This method provides rapid access to phthalimides starting from readily available

  在这里，我们报告了一种新颖的钯催化的羰基化氧化反应，用于合成具有高原子经济性和阶梯经济性的邻苯二甲酰亚胺。在我们的策略中，由醛和胺的缩合原位生成的亚胺和H 2 O分别作为自足的导向基团和亲核试剂。该方法以单罐方式从易于获得的材料开始快速获取邻苯二甲酰亚胺。有效地构造了各种邻苯二甲酰亚胺衍生物，包括具有医学和生物活性的含邻苯二甲酰亚胺的化合物。
• Ruthenium(II)-catalyzed N-substituted phthalimide synthesis via C–H activation/[3+2] annulation
  作者：Xue-Fen Dong、Juan Fan、Xian-Ying Shi、Ke-Yan Liu、Peng-Min Wang、Jun-Fa Wei

  DOI：10.1016/j.jorganchem.2014.12.016

  日期：2015.3

  intermolecular [3 + 2] annulation pathway for aromatic acids with isocyanates to afford N-substituted phthalimide in one step is demonstrated, which provides an efficient process to direct preparation of phthalimide from commercially available starting materials and environmentally benign catalysts. This cascade cyclization involves the direct functionalization of an ortho C–H bond and the subsequent

  一步一步证明了钌催化的芳香酸与异氰酸酯的分子间[3 + 2]环化路径，可在一步中得到N-取代的邻苯二甲酰亚胺，它提供了一种有效的方法，可从市售的起始原料和环境友好的催化剂中直接制备邻苯二甲酰亚胺。这种级联环化涉及邻C–H键的直接功能化以及随后的分子内亲核取代。除了在反应中产生水以外，没有理论上的浪费。
• Spectroscopic properties of aromatic dicarboximides. Part 2.—Substituent effect on the photophysical properties of N-phenyl-1,2-naphthalimide
  作者：Attila Demeter、Tibor Bérces、László Biczók、Véronique Wintgens、Pierre Valat、Jean Kossanyi

  DOI：10.1039/ft9949002635

  日期：——

  Absorption and fluorescence spectra, fluorescence decay times, fluorescence quantum yields and triplet yields have been determined for N-phenyl-1,2-naphthalimide and its phenyl-substituted methyl derivatives in different solvents. N-Phenyl-1,2-naphthalimide emits long-wavelength fluorescence in hexane (λmaxf= 550 nm) which is red shifted by methyl substitution at the meta and para positions of the phenyl ring and by using a solvent of higher polarity. The fluorescence decays on the sub-nanosecond timescale. When the N-phenyl-1,2-naphthalimide has o-methyl substituents in the phenyl group, they emit dual fluorescence. The location of the short-wavelength component is constant while that of the long-wavelength component is blue shifted as a result of o-methyl substitution. Ortho substitution also increases the decay time of the long-wavelength fluorescence. The results are explained in terms of vibronic interaction between the S1(ππ*) and S2(nπ*) excited states (pseudo-Jahn–Teller effect) which is enhanced by solvent relaxation and twisting of the phenyl ring towards a coplanar geometry.

  测定了 N-苯基-1,2-萘二甲酰亚胺及其苯基取代的甲基衍生物在不同溶剂中的吸收和荧光光谱、荧光衰减时间、荧光量子产率和三重态产率。N-苯基-1,2-萘二甲酰亚胺在正己烷中发出长波长荧光（δ "maxf= 550 nm），甲基取代苯环的元位和对位以及使用极性较高的溶剂会使荧光发生红移。荧光在亚纳秒级衰减。当 N-苯基-1,2-萘二甲酰亚胺的苯基中含有邻甲基取代基时，它们会发出双重荧光。短波分量的位置保持不变，而长波分量则由于邻甲基取代而发生蓝移。正交取代也增加了长波荧光的衰减时间。这些结果可以用 S1（ÏÏ*）和 S2（nÏ*）激发态之间的振子相互作用（伪贾恩泰勒效应）来解释，溶剂松弛和苯环向共面几何扭转增强了这种相互作用。