(E)-4-[2-(4-trifluoromethylphenyl)ethenyl]benzaldehyde | 255833-23-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-4-[2-(4-trifluoromethylphenyl)ethenyl]benzaldehyde
• 英文别名: (E)-4-(4-(trifluoromethyl)styryl)benzaldehyde；(E)-4-formyl-4'-(trifluoromethyl)stilbene；4-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]benzaldehyde
• CAS: 255833-23-9
• 化学式: C₁₆H₁₁F₃O
• 分子量: 276.258
• InChiKey: DQWKITQWYCYZII-OWOJBTEDSA-N

物化性质

• 沸点：
  361.0±42.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-4-[2-(4-trifluoromethylphenyl)ethenyl]benzaldehyde 在 哌啶 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  鉴定具有双重活性的5-芳基-4-噻唑烷酮衍生物作为醛糖还原酶抑制剂和抗氧化剂治疗糖尿病并发症

  摘要：

  在继续进行更有效的5-亚芳基-4-噻唑烷酮作为醛糖还原酶抑制剂的搜索中，一组新的适当取代的化合物（的4，5和8）进行了探讨。乙酸5，特别是5a和5h，被证明是该酶的令人感兴趣的抑制剂以及出色的抗氧化剂，它们可能能够抵消与糖尿病并发症以及其他疾病相关的氧化应激。分子对接实验支持SAR研究。

  DOI：

  10.1016/j.ejmech.2011.03.068
• 作为产物：
  描述：

  4-(diethyoxyphosphorylmethyl)benzoic acid methyl ester 在 manganese(IV) oxide 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 5.17h， 生成 (E)-4-[2-(4-trifluoromethylphenyl)ethenyl]benzaldehyde
  参考文献：
  名称：

  Synthesis and structure–activity relationships of novel, potent, orally active hypoxia-inducible factor-1 inhibitors

  摘要：

  Hypoxia-inducible factor-1 (HIF-1) is the chief transcription factor regulating hypoxia-driven gene expression. HIF-1 overexpression is associated with poor prognosis in several cancers and therefore represents an attractive target for novel antitumor agents. We explored small molecule inhibitors of the HIF-1 pathway. Using high-throughput-screening, we identified benzanilide compound 1 (IC50=560 nM) as a seed. Subsequent extensive derivatization led to the discovery of compounds 43a and 51d, with anti-HIF-1 activities in vitro (IC50=21 and 0.47 nM, respectively), and in vivo. Additionally, 43a (12.5-100mg/kg) also displayed in vivo anti-tumor efficacy, without influencing body weight.

  DOI：

  10.1016/j.bmc.2014.07.020

文献信息

• Electrocatalytic Oxidative Cleavage of Electron-Deficient Substituted Stilbenes in Acetonitrile−Water Employing a New High Oxidation Potential Electrocatalyst. An Electrochemical Equivalent of Ozonolysis
  作者：Xin Wu、Anthony P. Davis、Albert J. Fry

  DOI：10.1021/ol7026416

  日期：2007.12.1

  A series of symmetrical and unsymmetrical stilbenes bearing two or more strong electron-withdrawing groups were oxidatively cleaved to the corresponding aldehydes in high yield by electrocatalytic anodic oxidation in aqueous acetonitrile employing a new high oxidation potential triphenylamine electrocatalyst. The oxidations apparently involve the corresponding 1,2-diols, which are also converted to aldehydes in high yield under the same conditions.
• Synthesis and photoluminescent properties of conjugated aryl–vinyl dioctyl 2,6-dimethylbenzofuro[5,6-b]furan-3,7-dicarboxylate derivatives
  作者：Mariusz J. Bosiak、Marcin Rakowiecki、Katarzyna J. Orłowska、Dariusz Kędziera、Jörg Adams

  DOI：10.1016/j.dyepig.2013.07.006

  日期：2013.12

  The synthesis of highly fluorescent conjugated benzodifuran aryl vinyl systems, containing four double bonds and at least four phenyl rings, is described. The ethyl groups of diethyl 2,6-dimethylbenzofuro[5,6-b]furan-3,7-dicarboxylate, obtained by the Michael type condensation of p-benzoquinone and ethyl acetoacetate, were replaced by octyl groups via the transesterification reaction to improve the desired product solubility in common organic solvents. The dioctyl ester was brominated and Used for the Wittig reaction with stilbene aldehydes, obtained by the Heck reaction of 4-bromobenzaldehyde and an appropriate styrene. The products, obtained in 48-92% yield, exhibit the UV-Vis fluorescence with high quantum yields, 58-69%. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis and structure–activity relationships of novel, potent, orally active hypoxia-inducible factor-1 inhibitors
  作者：Satoshi Nagao、Yoshinobu Yamane、Setsuo Funasaka、Keigo Tanaka、Kazuki Miyazaki、Yoshihiko Kotake、Jun-ichi Kamata、Saori Watanabe-Miyano、Osamu Toyama、Yoichi Ozawa、Yoshiharu Mizui、Kiyoshi Okamoto、Daisuke Ito

  DOI：10.1016/j.bmc.2014.07.020

  日期：2014.10

  Hypoxia-inducible factor-1 (HIF-1) is the chief transcription factor regulating hypoxia-driven gene expression. HIF-1 overexpression is associated with poor prognosis in several cancers and therefore represents an attractive target for novel antitumor agents. We explored small molecule inhibitors of the HIF-1 pathway. Using high-throughput-screening, we identified benzanilide compound 1 (IC50=560 nM) as a seed. Subsequent extensive derivatization led to the discovery of compounds 43a and 51d, with anti-HIF-1 activities in vitro (IC50=21 and 0.47 nM, respectively), and in vivo. Additionally, 43a (12.5-100mg/kg) also displayed in vivo anti-tumor efficacy, without influencing body weight.
• Identification of 5-arylidene-4-thiazolidinone derivatives endowed with dual activity as aldose reductase inhibitors and antioxidant agents for the treatment of diabetic complications
  作者：Rosaria Ottanà、Rosanna Maccari、Marco Giglio、Antonella Del Corso、Mario Cappiello、Umberto Mura、Sandro Cosconati、Luciana Marinelli、Ettore Novellino、Stefania Sartini、Concettina La Motta、Federico Da Settimo

  DOI：10.1016/j.ejmech.2011.03.068

  日期：2011.7

  5-arylidene-4-thiazolidinones as aldose reductase inhibitors, a new set of suitably substituted compounds (4, 5 and 8) was explored. Acetic acids 5, particularly 5a and 5h, proved to be interesting inhibitors of the enzyme as well as excellent antioxidant agents that are potentially able to counteract the oxidative stress associated with both diabetic complications as well as other pathologies. Molecular

  在继续进行更有效的5-亚芳基-4-噻唑烷酮作为醛糖还原酶抑制剂的搜索中，一组新的适当取代的化合物（的4，5和8）进行了探讨。乙酸5，特别是5a和5h，被证明是该酶的令人感兴趣的抑制剂以及出色的抗氧化剂，它们可能能够抵消与糖尿病并发症以及其他疾病相关的氧化应激。分子对接实验支持SAR研究。