3,5-diformyl-4-hydroxybenzoic acid ethyl ester | 329904-04-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-diformyl-4-hydroxybenzoic acid ethyl ester
• 英文别名: ethyl 3,5-bisformyl-4-hydroxybenzoate；Ethyl 3,5-diformyl-4-hydroxybenzoate
• CAS: 329904-04-3
• 化学式: C₁₁H₁₀O₅
• mdl: MFCD01142870
• 分子量: 222.197
• InChiKey: DXSVGUGURKNATE-UHFFFAOYSA-N

物化性质

• 沸点：
  340.8±42.0 °C(Predicted)
• 密度：
  1.341±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5-diformyl-4-hydroxybenzoic acid ethyl ester 、 三羟甲基氨基甲烷 以 甲醇 为溶剂， 反应 6.0h， 以88.2%的产率得到Ethyl 3,5-bis[[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]iminomethyl]-4-hydroxybenzoate
  参考文献：
  名称：

  使用荧光蜘蛛样受体对水中的 5'-三磷酸腺苷 (ATP) 和胞苷-5'-三磷酸 (CTP) 进行比率检测

  摘要：

  通过三（羟甲基）氨基甲烷（TRIS）与各种2,6-二甲酰基苯酚（dfp）衍生物的席夫碱缩合，开发了一系列水溶性蜘蛛样受体分子。评估产品的阴离子传感特性。其中，具有甲氧基取代基的受体在 pH 7.2 的 100% 水性介质中以对比模式显示对 5'-三磷酸腺苷 (ATP) 和胞苷-5'-三磷酸 (CTP) 的选择性荧光传感。

  DOI：

  10.1002/ejoc.201403073
• 作为产物：
  描述：

  4-羟基-3,5-二甲基苯甲酸 在 chromium(VI) oxide 、 硫酸 、 乙酸酐 、 溶剂黄146 作用下， 反应 56.0h， 生成 3,5-diformyl-4-hydroxybenzoic acid ethyl ester
  参考文献：
  名称：

  Discovery of Novel Small Molecule Inhibitors of Dengue Viral NS2B-NS3 Protease Using Virtual Screening and Scaffold Hopping

  摘要：

  By virtual screening, compound 1 was found to be active against NS2B-NS3 protease (IC50 = 13.12 +/- 1.03 mu M). Fourteen derivatives (22) of compound 1 were synthesized, leading to the discovery of four new inhibitors with biological activity. In order to expand the chemical diversity of the inhibitors, small-molecule-based scaffold hopping was performed on the basis of the common scaffold of compounds 1 and 22. Twenty-one new compounds (23, 24) containing quinoline (new scaffold) were designed and synthesized. Protease inhibition assays revealed that 12 compounds with the new scaffold are inhibitors of NS2B-NS3 protease. Taken together, 17 new compounds were discovered as NS2B-NS3 protease inhibitors with IC50 values of 7.46 +/- 1.15 to 48.59 +/- 3.46 mu M, and 8 compounds belonging to two different scaffolds are active to some extent against DENY based on luciferase reporter replicon-based assays. These novel chemical entities could serve as lead structures for discovering therapies against DENY.

  DOI：

  10.1021/jm300146f

文献信息

• A trinuclear copper (II) complex derived from a chiral [3+3] phenol-based macrocycle: Synthesis, structure and magnetic properties
  作者：Lin Cheng、Jun Wang、Xiu-Ying Zhang、Shao-Hua Gou、Lei Fang

  DOI：10.1016/j.inoche.2014.07.032

  日期：2014.9

  enantiopure trinuclear Cu(II) complex of chiral phenol-based macrocyclic polyamine ligand, which is derived from the [3 + 3] condensation of 3,5-diformyl-4-hydroxyzoic acid ethyl ester with (1R,2R)-1,2-diaminocyclohexane and followed by borohydride reduction, has been synthesized and characterized. The circular dichroism (CD) spectra confirmed its structural chirality in the bulk sample. Variable temperature

  摘要 手性酚基大环多胺配体的对映体纯三核 Cu(II) 配合物，其衍生自 3,5-二甲酰基-4-羟基甲酸乙酯与 (1R,2R)-1 的 [3 + 3] 缩合,2-二氨基环己烷，然后进行硼氢化物还原，已被合成和表征。圆二色性 (CD) 光谱证实了其在大块样品中的结构手性。变温磁数据表明复合物中金属中心之间存在反铁磁耦合。
• “Donor–Two-Acceptor” Dye Design: A Distinct Gateway to NIR Fluorescence
  作者：Naama Karton-Lifshin、Lorenzo Albertazzi、Michael Bendikov、Phil S. Baran、Doron Shabat

  DOI：10.1021/ja308124q

  日期：2012.12.19

  The detection of chemical or biological analytes upon molecular reactions relies increasingly on fluorescence methods, and there is a demand for more sensitive, more specific, and more versatile fluorescent molecules. We have designed long wavelength fluorogenic probes with a turn-ON mechanism based on a donor-two-acceptor π-electron system that can undergo an internal charge transfer to form new fluorochromes

  基于分子反应的化学或生物分析物的检测越来越依赖于荧光方法，并且需要更灵敏、更特异和更通用的荧光分子。我们设计了基于供体-双受体 π 电子系统的开启机制的长波长荧光探针，该系统可以进行内部电荷转移以形成具有更长 π 电子系统的新荧光染料。几个潜在的供体和多个受体分子被结合到探针模块结构中，以产生通用的染料化合物。这个新的染料库在近红外 (NIR) 区域具有荧光发射。计算研究很好地再现了观察到的实验趋势，并提出了导致供体-双受体活性形式的高荧光和从潜伏形式观察到的低荧光的因素。HeLa 细胞的共聚焦图像表明所选染料的溶酶体渗透途径。这些染料通过开启激活机制发射 NIR 荧光的能力使它们成为体内成像应用的有希望的候选探针。
• Enhancement of fluorescent properties of near-infrared dyes using clickable oligoglycerol dendrons
  作者：Orit Redy-Keisar、Katharina Huth、Uwe Vogel、Bernd Lepenies、Peter H. Seeberger、Rainer Haag、Doron Shabat

  DOI：10.1039/c5ob00299k

  日期：——

  imaging. Here, we demonstrate that oligoglycerol dendrons effectively enhance the fluorescence properties of an NIR dye by increasing the solubility in water and the prevention of aggregate formation. First- and second-generation oligoglycerol dendrons were conjugated to an NIR dye via a dipolar-cycloaddition (click) reaction. The two new dye conjugates exhibited enhanced NIR fluorescent emission and

  由于近红外（NIR）荧光染料有可能用作体内成像的分子探针，因此受到越来越多的关注。在这里，我们证明了低聚甘油树枝状分子通过增加在水中的溶解度和防止聚集体形成，有效地增强了NIR染料的荧光特性。第一代和第二代低聚甘油树枝状分子通过偶极环加成（点击）反应。与单独的染料相比，这两种新的染料共轭物表现出增强的NIR荧光发射和显着更高的荧光量子产率。使用巨噬细胞荧光显微镜验证了与通常使用的荧光染料（例如Cy5和Cy7）相比，一种与低甘油连接的染料测得的高光稳定性。
• Tuning of multiple luminescence outputs and white-light emission from a single gelator molecule through an ESIPT coupled AIEE process
  作者：Arunava Maity、Firoj Ali、Hridesh Agarwalla、Bihag Anothumakkool、Amitava Das

  DOI：10.1039/c4cc09211b

  日期：——

  A single gelator molecule (1) shows an ESIPT coupled AIEE process for generating multiple luminescent colors, including white-light, with varying aggregation as a function of the water content in a THF–water mixture. Luminescent property of 1 is retained in gel as well as in solid state.

  一种凝胶化剂分子（1）显示出ESIPT耦合的AIEE过程，可以生成多种发光颜色，包括白光，其聚集形式随THF-水混合物中水含量的变化而不同。1的发光性质在凝胶和固态中都得以保留。
• ACTIVATABLE FLUOROGENIC COMPOUNDS AND USES THEREOF AS NEAR INFRARED PROBES
  申请人：Ramot at Tel-Aviv University Ltd.

  公开号：US20160229840A1

  公开（公告）日：2016-08-11

  Novel fluorogenic compounds designed such that upon a chemical event, compounds capable of emitting NIR light are generated, are disclosed. The compounds comprise two or more acceptor-containing moieties and a cleavable donor-containing moiety, being in complete pi-electrons conjugation and being such that no delocalization of pi-electrons is enabled. Also disclosed are fluorescent compounds generated upon subjecting the fluorogenic compounds to a chemical event (e.g., deprotonation). Also disclosed are uses of the fluorogenic compounds as NIR probed with a Turn-ON mechanism in monitoring presence and/or level of various analytes.

  本发明揭示了一种设计的新型荧光化合物，使得在化学事件发生时，能够发射近红外光的化合物被生成。这些化合物包括两个或更多的含有受体的基团和一个可剪切的含有给体的基团，完全处于π电子共轭状态，并且没有π电子的共轭扩散。本发明还揭示了在将荧光化合物置于化学事件（例如去质子化）中后生成的荧光化合物。本发明还揭示了将荧光化合物用作近红外探针的Turn-ON机制，以监测各种分析物的存在和/或水平。