5-羟基-6-硝基-2,3-二苯基-1-苯并呋喃-4-甲醛 | 1020808-50-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 中文名称: 5-羟基-6-硝基-2,3-二苯基-1-苯并呋喃-4-甲醛
• 英文名称: 5-hydroxy-6-nitro-2,3-diphenyl-1-benzofuran-4-carbaldehyde
• 英文别名: 5-hydroxy-6-nitro-2,3-diphenylbenzo[b]furan-4-carbaldehyde；5-Hydroxy-6-nitro-2,3-diphenyl-1-benzofuran-4-carbaldehyde
• CAS: 1020808-50-7
• 化学式: C₂₁H₁₃NO₅
• 分子量: 359.338
• InChiKey: IXXZMYWBPAYUMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-羟基-6-硝基-2,3-二苯基-1-苯并呋喃-4-甲醛 、 苯胺-15N 以70%的产率得到6-nitro-2,3-diphenyl-4-([15N]-phenyliminomethyl)-1-benzofuran-5-ol
  参考文献：
  名称：

  用于碱土金属阳离子的互变异构含冠化学传感器

  摘要：

  含冠-5-羟基-和5-羟基-6-硝基-2,3-二苯基苯并[的arylimines b呋喃-4- carbaldehydes合成]和它们的结构，光谱，发光，并借助于研究络合性能1 H和13 C NMR，IR，UV和质谱。在溶液中，这些化合物以benzenoid和quinoid互变异构体的平衡混合物形式存在。醌型的相对浓度按溶剂的顺序增加：甲苯，乙腈，2-丙醇，氯仿。在苯并[ b ]呋喃部分中存在强吸收性6-NO 2小组倾向于稳定醌型互变异构体。这一发现与DFT B3LYP / 6-311 ++ g（d，p）计算的结果相符。5-羟基-6-硝基-2,3-二苯基-1-苯并呋喃-4-甲醛的亚胺与碱金属和碱土金属离子的络合使互变异构平衡变为醌型，并伴随着蓝移。发射光谱。获得的席夫碱代表了一种新型的荧光互变异构化学传感器，用于Mg 2 +，Ca 2+（苯并15-冠-5衍生物）和Ba 2+（苯并18冠-6

  DOI：

  10.1016/j.tet.2008.01.096
• 作为产物：
  描述：

  5-羟基-2,3-二苯基-1-苯并呋喃-4-甲醛 在 硝酸 、 乙酸酐 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以34%的产率得到5-羟基-6-硝基-2,3-二苯基-1-苯并呋喃-4-甲醛
  参考文献：
  名称：

  用于碱土金属阳离子的互变异构含冠化学传感器

  摘要：

  含冠-5-羟基-和5-羟基-6-硝基-2,3-二苯基苯并[的arylimines b呋喃-4- carbaldehydes合成]和它们的结构，光谱，发光，并借助于研究络合性能1 H和13 C NMR，IR，UV和质谱。在溶液中，这些化合物以benzenoid和quinoid互变异构体的平衡混合物形式存在。醌型的相对浓度按溶剂的顺序增加：甲苯，乙腈，2-丙醇，氯仿。在苯并[ b ]呋喃部分中存在强吸收性6-NO 2小组倾向于稳定醌型互变异构体。这一发现与DFT B3LYP / 6-311 ++ g（d，p）计算的结果相符。5-羟基-6-硝基-2,3-二苯基-1-苯并呋喃-4-甲醛的亚胺与碱金属和碱土金属离子的络合使互变异构平衡变为醌型，并伴随着蓝移。发射光谱。获得的席夫碱代表了一种新型的荧光互变异构化学传感器，用于Mg 2 +，Ca 2+（苯并15-冠-5衍生物）和Ba 2+（苯并18冠-6

  DOI：

  10.1016/j.tet.2008.01.096

文献信息

• Benzoid-quinoid tautomerism of schiff bases and their structural analogs: LIII. Schiff bases derived from 5-hydroxy- and 5-hydroxy-6-nitro-2,3-diphenyl-1-benzofuran-4-carbaldehydes
  作者：E. N. Shepelenko、A. V. Tsukanov、Yu. V. Revinskii、A. D. Dubonosov、V. A. Bren’、V. I. Minkin

  DOI：10.1134/s1070428007040124

  日期：2007.4

  4-Aryl(alkyl)iminomethyl-5-hydroxy-and 4-aryl(alkyl)iminomethyl-5-hydroxy-6-nitro-2,3-diphenyl-1-benzofurans were synthesized and were shown to exist in solution as equilibrium mixtures of benzoid and quinoid tautomers. The fraction of the quinoid form increases with rise in the solvent polarity and in going from N-aryl to N-alkyl derivatives; introduction of an electron-acceptor substituent (nitro group) into the 6-position of the benzofuran system also favors formation of the quinoid tautomer. Complex formation of alkali and alkaline-earth metal cations with the 5-hydroxy-6-nitro-2,3-diphenyl-1-benzofuran-4-carbaldehyde imine having a benzo-15-crown-5 fragment on the nitrogen atom is accompanied by specific changes in the luminescence spectrum and in the state of tautomeric equilibrium, so that this system may be regarded as tautomeric fluorogenic chemosensor for metal cations.
• Benzoid-quinoid tautomerism of azomethines and their structural analogs: LIV. Dibenzo(benzo)-18-crown-6-containing Imines of 5-hydroxy-2,3-tetramethylene- and 5-Hydroxy-2,3-diphenylbenzo[b]furan-4-carbaldehydes
  作者：A. D. Dubonosov、A. V. Tsukanov、E. N. Shepelenko、Yu. V. Revinskii、V. A. Bren’、V. I. Minkin

  DOI：10.1134/s1070428009020079

  日期：2009.2

  Dibenzo(benzo)-18-crown-6-containing N-arylimines of 5-hydroxy-2,3-tetramethylene- and 5-hydroxy-2,3-diphenylbenzo[b]-furan-4-carbaldehydes were synthesized and their spectral luminescence properties were investigated. In solutions of 6-bromo- and 6-nitro-substituted compounds a tautomeric equilibrium exists between the benzoid and quinoid forms. In the course of complexing of crown-ether-imines of 5-hydroxy-6-nitro-2,3-diphenylbenzo[b]furan-4-carbaldehyde and 5-hydroxy-6-nitro-2,3-tetramethylenebenzo[b]furan-4-carbaldehyde with cations of alkali and alkaline earth metals the content of the quinoid form was found to decrease. This phenomenon was accompanied by essential changes in the absorption and fluorescence spectra characteristic of chemosensor systems with an intramolecular charge transfer (ICT).
• Tautomeric crown-containing chemosensors for alkali-earth metal cations
  作者：Alexander D. Dubonosov、Vladimir I. Minkin、Vladimir A. Bren、Evgenii N. Shepelenko、Alexey V. Tsukanov、Andrey G. Starikov、Gennadii S. Borodkin

  DOI：10.1016/j.tet.2008.01.096

  日期：2008.3

  crown-containing imines with alkali and alkali-earth metal ions shifts the tautomeric equilibrium to the quinoid forms and is accompanied by blue shifts of the emission spectra. The Schiff bases obtained represent a new type of fluorescent tautomeric chemosensor for Mg2+, Ca2+ (benzo-15-crown-5 derivative), and Ba2+ (benzo-18-crown-6 derivative) displaying diagnostic changes in both absorption and emission spectra

  含冠-5-羟基-和5-羟基-6-硝基-2,3-二苯基苯并[的arylimines b呋喃-4- carbaldehydes合成]和它们的结构，光谱，发光，并借助于研究络合性能1 H和13 C NMR，IR，UV和质谱。在溶液中，这些化合物以benzenoid和quinoid互变异构体的平衡混合物形式存在。醌型的相对浓度按溶剂的顺序增加：甲苯，乙腈，2-丙醇，氯仿。在苯并[ b ]呋喃部分中存在强吸收性6-NO 2小组倾向于稳定醌型互变异构体。这一发现与DFT B3LYP / 6-311 ++ g（d，p）计算的结果相符。5-羟基-6-硝基-2,3-二苯基-1-苯并呋喃-4-甲醛的亚胺与碱金属和碱土金属离子的络合使互变异构平衡变为醌型，并伴随着蓝移。发射光谱。获得的席夫碱代表了一种新型的荧光互变异构化学传感器，用于Mg 2 +，Ca 2+（苯并15-冠-5衍生物）和Ba 2+（苯并18冠-6