9-[2-(4-nitrophenyl)vinyl]anthracene | 60127-17-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9-[2-(4-nitrophenyl)vinyl]anthracene
• 英文别名: (E)-9-(4-nitrostyryl)anthracene；trans-1-(p-Nitro-phenyl)-2-(9-anthryl)-ethylene；9-(4-Nitro-β-styryl)-anthracen；9-[(E)-2-(4-Nitrophenyl)ethenyl]anthracene
• CAS: 60127-17-5
• 化学式: C₂₂H₁₅NO₂
• 分子量: 325.367
• InChiKey: UPYXQXXAUPVWFL-SDNWHVSQSA-N

物化性质

• 熔点：
  221-222 °C(Solv: ethanol (64-17-5); chloroform (67-66-3))
• 沸点：
  521.1±25.0 °C(Predicted)
• 密度：
  1.287±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2904209090

反应信息

• 作为反应物：
  描述：

  9-[2-(4-nitrophenyl)vinyl]anthracene 以 甲基环己烷 为溶剂， 生成 9-[(E)-2-(4-Nitro-phenyl)-vinyl]-anthracene
  参考文献：
  名称：

  具有给电子和受电子取代基的反式-1-（9-蒽基）-2-（4-R-苯基）乙烯的激发态性质[R = N（CH3）2，OCH3，CH3，Br，CN，和NO2]

  摘要：

  The der-ay pathways of the lowest excited singlet state (1t*) of trans-1-(9-anthryl)-2-(4-R-phenyl)ethylenes (trans-R-StAs, where R = N(CH3)2, OCH3, CH3, Br, CN, and NO2 On the 4-Position of the styryl) were studied in solution at room and low temperatures. Fluorescence lifetime (tau(f)) and quantum yield (PHI(f)) as well as the yield (PHI(T)) and spectral and kinetic properties of the lowest triplet state were determined by steady-state and transient techniques. The solvent polarity has a large effect on the Stokes shift for (H3C)2N- and O2N-StA, the two derivatives with the strongest electron-donating and -accepting substituents. The smallest changes in PHI(f) and PHI(T), in comparison with the case of parent 9-StA, are caused by the Br or CH3 groups. For O2N- and (H3C)2N-StA, and to a lesser degree for NC- and H3CO-StA, PHI(f) and tau(f) become significantly smaller with increasing solvent polarity. Efficient deactivation by charge transfer via an excited singlet state with essentially trans configuration (A*) is proposed for these derivatives. The 1t* --> A* relaxation pathway in polar solvents is activated and competes with fluorescence and intersystem crossing. For NC-, H3CO-, and (H3C)2N-StA at room temperature trans --> cis photoisomerization occurs with substantial quantum yield (PHI(t --> c)) in those solvents in which the presence of the postulated A*-state efficiency reduces fluorescence and intersystem crossing. A contribution of a triplet mechanism to trans --> cis photoisomerization can be excluded throughout. A special case is O2N-StA, which exhibits virtually no photochemistry in both nonpolar and polar solvents, but PHI(t --> c) is up to 0.2 in slightly polar solvents, e.g., toluene.

  DOI：

  10.1021/j100145a012
• 作为产物：
  描述：

  9-氯甲基蒽 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 2.0h， 生成 9-[2-(4-nitrophenyl)vinyl]anthracene
  参考文献：
  名称：

  具有给电子和受电子取代基的反式-1-（9-蒽基）-2-（4-R-苯基）乙烯的激发态性质[R = N（CH3）2，OCH3，CH3，Br，CN，和NO2]

  摘要：

  The der-ay pathways of the lowest excited singlet state (1t*) of trans-1-(9-anthryl)-2-(4-R-phenyl)ethylenes (trans-R-StAs, where R = N(CH3)2, OCH3, CH3, Br, CN, and NO2 On the 4-Position of the styryl) were studied in solution at room and low temperatures. Fluorescence lifetime (tau(f)) and quantum yield (PHI(f)) as well as the yield (PHI(T)) and spectral and kinetic properties of the lowest triplet state were determined by steady-state and transient techniques. The solvent polarity has a large effect on the Stokes shift for (H3C)2N- and O2N-StA, the two derivatives with the strongest electron-donating and -accepting substituents. The smallest changes in PHI(f) and PHI(T), in comparison with the case of parent 9-StA, are caused by the Br or CH3 groups. For O2N- and (H3C)2N-StA, and to a lesser degree for NC- and H3CO-StA, PHI(f) and tau(f) become significantly smaller with increasing solvent polarity. Efficient deactivation by charge transfer via an excited singlet state with essentially trans configuration (A*) is proposed for these derivatives. The 1t* --> A* relaxation pathway in polar solvents is activated and competes with fluorescence and intersystem crossing. For NC-, H3CO-, and (H3C)2N-StA at room temperature trans --> cis photoisomerization occurs with substantial quantum yield (PHI(t --> c)) in those solvents in which the presence of the postulated A*-state efficiency reduces fluorescence and intersystem crossing. A contribution of a triplet mechanism to trans --> cis photoisomerization can be excluded throughout. A special case is O2N-StA, which exhibits virtually no photochemistry in both nonpolar and polar solvents, but PHI(t --> c) is up to 0.2 in slightly polar solvents, e.g., toluene.

  DOI：

  10.1021/j100145a012

文献信息

• Direct C≡C Triple Bond Formation from the C=C Double Bond and Direct Hydroxylation into the<i>o</i>-Position of a Nitro Group on the Benzene Nucleus with Potassium<i>t</i>-Butoxide in<i>N</i>,<i>N</i>-Dimethylformamide in the Air
  作者：Shuzo Akiyama、Kunihiko Tajima、Shin’ichi Nakatsuji、Kenichiro Nakashima、Kazuko Abiru、Miwa Watanabe

  DOI：10.1246/bcsj.68.2043

  日期：1995.7

  4-diethylamino-4′ -nitrostilbene was measured to identify an anion radical species expected for explanation of the mechanism of the dehydrogenation reaction. Further, cyclic voltammetric measurements of a series of stilbenes and diphenylacetylenes were carried out in connection with the above mechanism. In many cases, interestingly, the use of a large excess of t-BuOK brought about succeeding hydroxylation

  在空气中的 N,N-二甲基甲酰胺中用叔丁醇钾 (t-BuOK) 处理从 C=C 双键直接形成 C≡C 炔键的新方法和简便方法已在 9,10-双(4-取代苯乙烯基)蒽系列、4-取代4'-硝基二苯乙烯系列和1-(对硝基苯基)-4-(对-取代苯基)-1,3-丁二烯系列；已经审查了其范围和局限性。测量针对 4-二乙氨基-4'-硝基二苯乙烯的反应的 ESR 光谱，以确定预期用于解释脱氢反应机理的阴离子自由基种类。此外，结合上述机理进行了一系列二苯乙烯和二苯乙炔的循环伏安测量。在许多情况下，有趣的是，使用大量过量的 t-BuOK 导致后续羟基化到苯核上硝基的邻位。简单的羟基化可用于合成取代的 5-（芳基乙炔基）-2-硝基苯酚，...
• New Anthracenyl-Substituted Phosphonates: Synthesis and Utility
  作者：K. Kumara Swamy、Venu Srinivas、K. Pavan Kumar、K. Praveen Kumar

  DOI：10.1055/s-2007-965947

  日期：2007.3

  Chlorination of α-hydroxyphosphonate anthracen-9-yl(5,5-dimethyl-2-oxo-2λ 5 -1,3,2-dioxaphosphinan-2-yl)methanol ( 11) using thionyl chloride unexpectedly yields 10-(5,5-dimethyl-2-oxo-2λ 5 -1,3,2-dioxaphosphinan-2-ylmethylene)anthracen-9(10 H)-one ( 13), 2-(10-chloroanthracen-9-ylmethyl)-5,5-dimethyl-2λ 5 -1,3,2-dioxaphosphinan-2-one ( 14), and 10-(5,5-dimethyl-2-oxo-2λ 5 -1,3,2-dioxaphosphinan-2-ylmethylene)-9

  使用亚硫酰氯对 α-羟基膦酸酯 anthracen-9-yl(5,5-dimethyl-2-oxo-2λ 5 -1,3,2-dioxaphosphinan-2-yl) 甲醇 (11) 进行氯化意外得到 10-(5, 5-dimethyl-2-oxo-2λ 5 -1,3,2-dioxaphosphinan-2-ylmethylene)anthracen-9(10 H)-one (13), 2-(10-chloroanthracen-9-ylmethyl)-5, 5-dimethyl-2λ 5 -1,3,2-dioxaphosphinan-2-one ( 14) 和 10-(5,5-dimethyl-2-oxo-2λ 5 -1,3,2-dioxaphosphinan-2-ylmethylene )-9,10-dihydroanthracen-9-ol (15) 除了 2-[anthracen-
• Synthesis and antiproliferative action of a novel series of maprotiline analogues
  作者：Y.M. McNamara、S.A. Bright、A.J. Byrne、S.M. Cloonan、T. McCabe、D.C. Williams、M.J. Meegan

  DOI：10.1016/j.ejmech.2013.10.076

  日期：2014.1

  The synthesis of a diverse library of compounds structurally related to maprotiline, a norepinephrine reuptake transporter (NET) selective antidepressant which has recently been identified as a novel in vitro antiproliferative agent against Burkitt's lymphoma (BL) cell lines is reported. A series of 9,10-dihydro-9,10-ethanoanthracenes were synthesised with modifications to the bridge of the dihydroethanoanthracene structure and with alterations to the basic side chain. A number of compounds were found to reduce cell viability to a greater extent than maprotiline in BL cell lines. In addition a related series of novel 9-substituted anthracene compounds were investigated as intermediates in the synthesis of 9,10-dihydro-9,10-ethanoanthracenes. These compounds proved the most active from the screen and were found to exert a potent caspase-dependant apoptotic effect in the BL cell lines, while having minimal effect on the viability of peripheral blood mononuclear cells (PBMCs). Compounds also displayed activity in multi-drug resistant (MDR) cells. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Hann,R.A., Journal of the Chemical Society. Perkin transactions I, 1974, p. 1379 - 1380
  作者：Hann,R.A.

  DOI：——

  日期：——
• Gupta, K. C.; Pathak, P. K.; Saxena, B. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 196 - 198
  作者：Gupta, K. C.、Pathak, P. K.、Saxena, B. K.、Srivastava, Nirupma

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  日期：——