5-羟基-2,3-二苯基-1-苯并呋喃-4-甲醛 | 917867-68-6

• 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-2,3-二苯基-1-苯并呋喃-4-甲醛
• 英文名称: 5-hydroxy-2,3-diphenyl-1-benzofuran-4-carbaldehyde
• 英文别名: 5-hydroxy-2,3-diphenylbenzo[b]furan-4-carbaldehyde；5-Hydroxy-2,3-diphenyl-1-benzofuran-4-carbaldehyde
• CAS: 917867-68-6
• 化学式: C₂₁H₁₄O₃
• 分子量: 314.34
• InChiKey: HAWWNWBKOJPAEQ-UHFFFAOYSA-N

物化性质

• 熔点：
  186-187 °C(Solv: toluene (108-88-3))
• 沸点：
  465.3±45.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 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：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  5-hydroxy-2,3-diphenylbenzo[b]furan 、 苯亚胺代甲酸乙酯 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.25h， 以48%的产率得到5-羟基-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

• Effect of bulky substituents on the photochromic properties of indoline spiropyrans containing an annelated aromatic or heteroaromatic fragment
  作者：R. V. Tyurin、B. S. Lukyanov、A. V. Chernyshev、V. I. Malay、A. S. Kozlenko、N. S. Tkacheva、O. N. Burov、M. B. Lukyanova

  DOI：10.1134/s0012500816090081

  日期：2016.9

  Novel indoline spiropyrans containing bulky neopentyl substituents at the nitrogen atom of the indoline fragment were prepared. The structure of the obtained compounds was established by a set of physicochemical methods of analysis. Comparison was made for the spectral absorption and kinetic parameters of the obtained compounds and their analogs containing methyl and benzyl substituents instead of

  制备了在二氢吲哚片段的氮原子处含有庞大的新戊基取代基的新型二氢吲哚螺吡喃。所得化合物的结构是通过一系列理化分析方法确定的。对所得化合物及其含有甲基和苄基取代基而不是新戊基取代基的类似物的光谱吸收和动力学参数进行了比较。
• Photo- and Thermochromic Spiropyrans 42.* The Effect of Structural Factors on the Photochromic Properties of Indolinospiro-Pyrans Containing a Condensed Furan Fragment
  作者：R. V. Tyurin、B. S. Lukyanov、A. V. Chernyshev、G. S. Borodkin、K. N. Khalanskii、L. V. Chepeleva、M. B. Lukyanova

  DOI：10.1007/s10593-014-1528-x

  日期：2014.8

  the benzopyran part of the molecule. The structure of these compounds was established by IR and multinuclear NMR spectroscopy. A study was carried out on the effect of the fused benzene ring and bulky N-benzyl substituent on the photochromic properties of these compounds in solution and in a polymer matrix. Dynamic NMR spectroscopy was used to study the thermally induced isomerization of the N-benzyl

  报道了在分子的苯并吡喃部分中含有融合的呋喃片段的一系列N-取代的吲哚螺并吡喃的合成。这些化合物的结构通过IR和多核NMR光谱法确定。研究了稠合苯环和庞大的N-苄基取代基对溶液和聚合物基质中这些化合物的光致变色性能的影响。动态NMR光谱用于研究N-苄基衍生物的热诱导的异构化。
• 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).
• Novel photochromic indolinospiropyrans containing phenyl substituents in the condensed furan moiety
  作者：B. S. Lukyanov、E. N. Shepelenko、V. A. Bren、M. B. Lukyanova、S. O. Bezuglyi

  DOI：10.1007/s10593-006-0056-8

  日期：2006.1