4-(4-methylbenzoyloxy)benzaldehyde | 115883-85-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 4-(4-methylbenzoyloxy)benzaldehyde
• 英文别名: 4-Formylphenyl 4-methylbenzoate；(4-formylphenyl) 4-methylbenzoate
• CAS: 115883-85-7
• 化学式: C₁₅H₁₂O₃
• mdl: MFCD03142343
• 分子量: 240.258
• InChiKey: FMRSEGPACXSFEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  4-(4-methylbenzoyloxy)benzaldehyde 在 potassium permanganate 、 盐酸 作用下， 以 丙酮 、 水 为溶剂， 以90%的产率得到4-(4-methylbenzoyloxy)benzoic acid
  参考文献：
  名称：

  Zheng, Min-Yan; Wei, Yong-Sheng; Fan, Guang, Asian Journal of Chemistry, 2012, vol. 24, # 1, p. 161 - 164

  摘要：

  DOI：
• 作为产物：
  描述：

  对甲基苯甲酸 在 氯化亚砜 、 三乙胺 作用下， 生成 4-(4-methylbenzoyloxy)benzaldehyde
  参考文献：
  名称：

  Design, Synthesis and Evaluation of Rhodanine Derivatives as Aldose Reductase Inhibitors

  摘要：

  Aldose reductase (ALR) enzyme plays a significant role in conversion of excess amount of glucose into sorbitol in diabetic condition, inhibitors of which decrease the secondary complication of diabetes mellitus. To understand the structural interaction of inhibitors with ALR enzyme and develop more effective ALR inhibitors, a series of substituted 5‐phenylbenzoate containing N‐substituted rhodanine derivatives were synthesized and evaluated for their in vitro ALR inhibitory activity. Docking studies of these compounds were carried out, which revealed that the 5‐phenylbenzoate moiety deeply influenced the key π‐π stacking while 4‐oxo‐2‐thioxothiazolidines contributed in hydrogen bond interactions. The phenyl ring of benzylidene system occupied in specific pocket constituted from Phe115, Phe122, Leu300 and Cys303 while the rhodanine ring forms a tight net of hydrogen bond with Val47 at anionic binding site of the enzyme. The structural insights obtained from the docking study gave better understanding of rhodanine and macromolecular interaction and will help us in further designing and improving of ALR inhibitory activity of rhodanine analogs.

  DOI：

  10.1111/cbdd.12369

文献信息

• Effects of Branching of the Ester Alkyl Chain on the Mesomorphic Properties of Alkyl 4-[4-(4-Substituted benzoyloxy)benzylideneamino]benzoates
  作者：Hiroyuki Matsuzaki、Yoshio Matsunaga

  DOI：10.1246/bcsj.63.2300

  日期：1990.8

  The mesomorphic properties of five homologous series of alkyl 4-[4-(4-X-substituted benzoyloxy)benzylideneamino]benzoates, where X=CN,NO2, CH3, Cl, and CH3COO, have been studied. The ester alkyl groups employed were the following eleven types: ethyl and propyl and their mono-, di-, and trimethyl-substituted ones. Although the introduction of the first branching methyl group to the ester alkyl chain depresses the nematic stability, the second and/or third groups may either further depress or enhance the stability, depending upon the nature of the substituent X. While all of the members of the cyano and nitro derivatives are purely nematogenic, many members of the other three series display a smectic A phase, as well as a nematic phase. In addition to the above-mentioned esters, the butyl, pentyl, and their monomethyl-substituted esters were examined in order to demonstrate that the effects on the thermal stability of the smectic A phase of the branching of the ester alkyl chain and those of the substituent X are also interdependent.

  五个同系物系列的烷基4-[4-(4-X取代苯甲氧基)苯亚胺]苯甲酸酯的介质相性质进行了研究，其中X=CN，NO2，CH3，Cl和CH3COO。所采用的酯烷基有以下十一种类型：乙基、丙基及其单、双、三甲基取代物。尽管向酯烷基链引入第一个分枝甲基会降低向列相的稳定性，但第二个和/或第三个取代基可能会进一步降低或增强稳定性，这取决于取代基X的性质。虽然所有的氰基和硝基衍生物都是纯粹的向列液晶，但其他三类中的许多成员显示出层状A相，以及向列相。除了上述酯类之外，还检查了丁基、戊基及其单甲基取代的酯，以证明酯烷基链的分枝及取代基X对层状A相热稳定性的影响也是相互依存的。
• Exploiting the 4-Phenylquinazoline Scaffold for the Development of High Affinity Fluorescent Probes for the Translocator Protein (TSPO)
  作者：Ciro Milite、Elisabetta Barresi、Eleonora Da Pozzo、Barbara Costa、Monica Viviano、Amalia Porta、Anna Messere、Gianluca Sbardella、Federico Da Settimo、Ettore Novellino、Sandro Cosconati、Sabrina Castellano、Sabrina Taliani、Claudia Martini

  DOI：10.1021/acs.jmedchem.7b01031

  日期：2017.9.28

  The quinazoline class was exploited to search for a new translocator protein (TSPO) fluorescent probe endowed with improved affinity and residence time (RT). Computational studies on an “in-house” collection of quinazoline derivatives, featuring highly steric demanding groups at the amide nitrogen, suggested that, despite their molecular extension, these ligands are still easily lodged in the TSPO

  利用喹唑啉类来寻找一种新的易位蛋白（TSPO）荧光探针，该探针具有改善的亲和力和停留时间（RT）。对喹唑啉衍生物“内部”集合的计算研究表明，酰胺氮上具有高度空间要求的基团，尽管它们具有分子延伸性，但这些配体仍很容易沉积在TSPO结合位点。结合分析支持了这一假设，突出了这些配体的纳摩尔/亚纳摩尔亲和力低，以及代表性化合物11的RT较高关于我们先前报道的基于吲哚的荧光探针。由于酰胺氮原子可以被庞大的基团取代，我们通过在此位置进行荧光标记来开发基于喹唑啉的成像工具。确定了具有相关TSPO亲和力，良好的光谱特性和改进的RT的探针。荧光显微镜的结果表明，这些探针在U343细胞系的线粒体水平上特异性标记了TSPO。
• Effects of Polysubstitution on Mesomorphic Properties: Chloro and Methyl Derivatives of<i>N</i>-[4-(4-Substituted benzoyloxy)benzylidene]anilines
  作者：Hiroyuki Hasegawa、Tatsuya Masuda、Yoshio Matsunaga、Sachiko Seo、Kazuaki Yasuhara

  DOI：10.1246/bcsj.62.2875

  日期：1989.9

  The effects of mono-, di-, and trichloro substitution of the aniline moiety on the nematic-isotropic transition temperature of N-[4-(4-X-substituted benzoyloxy)benzylidene]anilines, where X=CH3O, CH3, or Cl, have been studied, while paying particular attention to the vicinal chlorines. While the substituent on the 2 or 3 position of the aniline moiety lowers the transition temperature of the parent

  苯胺部分的单、二和三氯取代对 N-[4-(4-X-取代的苯甲酰氧基)苄叉]苯胺的向列各向同性转变温度的影响，其中 X=CH3O、CH3 或 Cl , 已被研究，同时特别注意邻氯。虽然苯胺部分 2 或 3 位上的取代基降低了母体化合物和 4-氯衍生物的转变温度，但 2,3-二氯衍生物显示出高于 2- 或 3-氯衍生物的温度衍生物。此外，2,3,4-三氯衍生物的转变温度高于3,4-二氯衍生物的转变温度，略低于2,4-二氯异构体的转变温度。相反，无论其他取代基的位置如何，4-取代基的引入都会增加温度。
• Chemical Modification of Coumarin Dimer and HIV-1 Integrase Inhibitory Activity.
  作者：Pili Chih-Min Mao、Jean-Francois Mouscadet、Herve Leh、Christian Auclair、Ling-Yih Hsu

  DOI：10.1248/cpb.50.1634

  日期：——

  A systematic series of chemically modified coumarin dimmers has been synthesized and tested for their inhibitory activity against HIV-1 integrase. We observed that modified coumarin dimmers containing hydrophobic moiety on the linker display potent inhibitory activities.

  我们合成了一系列经过化学修饰的香豆素二聚体，并测试了它们对 HIV-1 整合酶的抑制活性。我们发现，在连接体上含有疏水分子的修饰香豆素二聚体具有很强的抑制活性。
• Synthesis, in vitro antioxidant activity, and physicochemical properties of novel 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives
  作者：Haydar Yüksek、Ebru Koca、Özlem Gürsoy-Kol、Onur Akyıldırım、Mustafa Çelebier

  DOI：10.1016/j.molliq.2015.02.038

  日期：2015.6

  characterized using IR, 1H NMR, 13C NMR, and UV spectral data. In addition, the synthesized compounds were analyzed for their potential in vitro antioxidant activities, including reducing power, free radical scavenging and metal chelating activity. These antioxidant activities were compared to those from standard antioxidants, such as EDTA, BHA, BHT and α-tocopherol. Moreover, compounds 4 were titrated potentiometrically

  在这项研究中，八个新的3-烷基（芳基）-4- [4-（4-甲基苯甲酰）苄叉氨基] -4,5-二氢-1 H -1,2,4-三唑-5-酮（4）化合物通过3-烷基（芳基）-4-氨基-4,5-二氢-1 H -1,2,4-三唑-5-酮（3）与4-（4-甲基苯并）苯甲醛（1）。使用IR，1 H NMR，13对8种化合物进行了表征1 H NMR和UV光谱数据。此外，分析了合成化合物的潜在体外抗氧化活性，包括还原能力，自由基清除作用和金属螯合活性。将这些抗氧化剂活性与标准抗氧化剂（例如EDTA，BHA，BHT和α-生育酚）的抗氧化剂活性进行了比较。此外，在四种非水溶剂（异丙醇，叔丁醇，丙酮和N，N-二甲基甲酰胺）中，用氢氧化四丁铵电位滴定化合物4。因此，半中和电位值和相应的p K a在所有情况下均确定值。另外，使用HPLC研究了合成化合物的亲脂性。使用Coats–Redfern和Horowitz–Metz