methyl 3,4,5-triethoxybenzoate | 39666-77-8

• 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: methyl 3,4,5-triethoxybenzoate
• CAS: 39666-77-8
• 化学式: C₁₄H₂₀O₅
• mdl: MFCD02244782
• 分子量: 268.31
• InChiKey: FNXHLTFMRSQMPK-UHFFFAOYSA-N

物化性质

• 熔点：
  53 °C
• 沸点：
  325.3±9.0 °C(Predicted)
• 密度：
  1.078±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3,4,5-triethoxybenzoate 在 4-二甲氨基吡啶 、 氢氧化钾 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  Molecular Control of Macroscopic Cubic, Columnar, and Lamellar Organizations in Luminescent Lanthanide-Containing Thermotropic Liquid Crystals

  摘要：

  The connection of lipophilic gallic acid derivatives at the 5,5'- or 6,6'-positions of the rigid 2,6bis(1-ethyl-benzimidazol-2-yl)pyridine core provides two pro-mesogenic tridentate ligands L10 and L12, whose molecular shapes, anisometries, and directional intermolecular pi-stacking can be tuned. X-ray diffraction data in the crystalline state, combined with solution H-1 NMR measurements, show that complexation with trivalent lanthanides, Ln(III), produces the neutral hemi-disklike complexes [Ln(Li)(NO3)(3)] (i = 10, 12), which dimerize to give the rodlike bimetallic complexes [Ln(2)(Li)(2)(NO3)(6)] at lower temperature. The relevant thermodynamic parameters for the latter process depend on the nature of the ligand, the size of the metal ion, and the strength of the intermolecular interactions involved in the condensed phase. These three-dimensional models obtained for the complexes in the crystals and in solution are eventually confronted with small-angle XRD profiles recorded in the intermediate thermotropic liquid crystalline phase, in which the rigidity of the packed polyaromatic cores is maintained, while the alkyl chains are molten. According to the specific geometries and nuclearities of the molecular complexes, three types of mesophases (lamellar, columnar, and cubic) can be induced, which provides a direct correlation between the microscopic arrangements and the macroscopic ordering in lanthanicle-containing metallomesogens.

  DOI：

  10.1021/ja0446101
• 作为产物：
  描述：

  没食子酸 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 methyl 3,4,5-triethoxybenzoate
  参考文献：
  名称：

  Depigmenting Activity and Low Cytotoxicity of Alkoxy Benzoates or Alkoxy Cinnamte in Cultured Melanocytes

  摘要：

  为了获得有效且安全的局部脱色剂，我们合成了含百里酚基团的羟基苯甲酸盐、烷氧基苯甲酸盐和3,4,5-三甲氧基肉桂酸盐，并对其在培养的黑素细胞中抑制黑色素合成的高水平活性进行了筛选。我们使用小鼠黑素细胞系测试了八种化合物的脱色效果和细胞毒性。研究发现，通过将3,4,5-三烷氧基苯甲酸和3,4,5-三甲氧基肉桂酸与百里酚结合合成的3,4,5-三烷氧基苯甲酸盐和3,4,5-三甲氧基肉桂酸盐显示出强大的脱色效果和低细胞毒性。化合物4h，5-甲基-2-（甲基乙基）苯基（2E）-3-（3,4,5-三甲氧基苯基）丙-2-烯酸酯，显示出最强的脱色效果（IC50=10 μM）和低细胞毒性（IC50=200 μM）。

  DOI：

  10.1248/cpb.51.1085

文献信息

• Influence of alkoxy tail length on the phase behaviour of mesogen-jacketed liquid crystalline polymers with fan-shaped pendants
  作者：Chang-An Yang、Guo Wang、He Lou Xie、Hai Liang Zhang

  DOI：10.1016/j.polymer.2010.08.007

  日期：2010.9

  synthesized. Then, their corresponding polymers P-tri-OCmH2m + 1 (m = 1, 2, 4, 6, 8, 10, 12) were synthesized by free radical polymerization. The chemical structure of the monomers was confirmed by elemental analysis, 1H NMR and 13C NMR. The molecular characterization of polymers was performed with 1H NMR, gel permeation chromatography (GPC). The thermal stability of polymers was investigated by thermogravimetric

  一系列2、5-双[[3、4、5-三烷氧基苄基）氧羰基]苯乙烯的新单体（表示为M-tri-OC m H 2m  +  1，m  = 1，2，4，4，6，8 ，10、12，其中m表示烷氧基中的碳原子数）被设计并合成。然后， 通过自由基聚合合成它们相应的聚合物P-tri-OC m H 2m  +1（m = 1、2、4、6、8、10、12）。单体的化学结构通过元素分析，1 H NMR和13 C NMR确认。用1对聚合物进行分子表征1 H NMR，凝胶渗透色谱法（GPC）。通过热重分析（TGA）研究了聚合物的热稳定性。使用差示扫描量热法（DSC），偏振光显微镜（PLM），一维和二维（一维和二维）广角X射线衍射（WAXD）研究了相结构和跃迁行为。我们发现，P-三OC米ħ 2米 + 1（米 短= 1，2）ñ -烷氧基的取代基的尾部形式柱状向列型（Φ Ñ）相; 与烷氧基尾部的增加的长度，P-三OC米ħ 2米 +
• [EN] DIARYL TREHALOSE COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS DE TRÉHALOSE DE DIARYLE ET LEURS UTILISATIONS
  申请人：THE UNIV OF MONTANA

  公开号：WO2019165114A1

  公开（公告）日：2019-08-29

  Disclosed herein are diaryl trehalose compounds and methods of use thereof, for example as vaccine adjuvants.

  本文披露了二芳基海藻糖化合物及其使用方法，例如作为疫苗佐剂。
• Expanding the Library of 2-Phenylbenzotellurazoles: Red-Shifting Effect­ of Ethoxy Functionalities on the UV/Vis Absorption Properties
  作者：Deborah Romito、Leonardo Amendolare、Davide Bonifazi、Krishnan K. Kalathil

  DOI：10.1055/s-0041-1737898

  日期：2023.1

  functionalized with ethoxy chains. Changing the number and the position of these functional groups determines differences in the self-assembly in the solid state, as well as in the photophysical properties of the targeted molecules. As anticipated by theoretical calculations of the HOMO-LUMO gap of each molecule, the presence of ethoxy chains in o- and p-positions determines up to 20 nm red-shifts

  这项工作描述了在 2 位带有苯环的新型苯并碲唑系列的高产率合成，该苯环被不同的乙氧基链官能化。改变这些官能团的数量和位置决定了固态自组装的差异，以及目标分子的光物理特性。正如对每个分子的 HOMO-LUMO 间隙的理论计算所预期的那样，与未取代的苯并碲唑相比，邻位和对位乙氧基链的存在决定了吸收峰中高达 20 nm 的红移。同样，对于那些带有o的衍生物，在125 Te NMR 光谱的化学位移中观察到更显着的变化。-和对-乙氧基官能化。
• Synthesis and properties of hole-transporting triphenylamine-derived dendritic compounds
  作者：Renji R. Reghu、Jurate Simokaitiene、Juozas V. Grazulevicius、Steponas Raisys、Karolis Kazlauskas、Saulius Jursenas、Vygintas Jankauskas、Antonio Reina

  DOI：10.1016/j.dyepig.2014.12.013

  日期：2015.4

  Materials based on triphenylamino core linked with different alkoxyphenyl-substituents through olefinic spacers were synthesised, and their thermal, photophysical and photoelectrical properties were investigated. The synthesized compounds showed relatively good thermal stability. Derivatives containing shorter alkyl chains displayed glass-forming ability, while the compounds containing flexible alkyl termini demonstrated liquid-crystalline behaviour. Flexible alkyl substituents at the periphery of tri-phenylamine derivatives prevented the close packing of chromophores and hence, they showed relatively similar absorption and fluorescence in thin-films and solutions. Reduction in fluorescence quantum yield in thin-films upon decreasing the size of peripheral alkyl substituents confirmed enhanced intermolecular interactions and in turn, suggested migration-induced exciton quenching at nonradiative decay sites. Ionization potentials of thin solid layers estimated by photoelectron emission spectroscopy ranged from 5.21 to 5.47 eV. Hole-drift mobility of ethyl substituted triphenylamine measured using xerographic time-of-flight (XTOF) method was 1.3 x 10(-3) cm(2) V-1 s(-1) at an electric field of 10(6) Vcm(-1). (C) 2014 Elsevier Ltd. All rights reserved.
• 2,4-Diamino-5-benzylpyrimidines as antibacterial agents. 7. Analysis of the effect of 3,5-dialkyl substituent size and shape on binding to four different dihydrofolate reductase enzymes
  作者：Barbara Roth、Barbara S. Rauckman、Robert Ferone、David P. Baccanari、John N. Champness、Richard M. Hyde

  DOI：10.1021/jm00385a017

  日期：1987.2

  A group of trimethoprim (TMP) analogues containing 3,5-dialkyl(or halo)-4-alkoxy, -hydroxy, or -amino substitution were analyzed in terms of their inhibitory activities against four dihydrofolate reductase (DHFR) isozymes. Although selectivities were lower than with TMP, the activities against vertebrate DHFR were usually at least 2 orders of magnitude less than against enzymes from microbial sources. However, the profiles of activity were remarkably similar for rat, Neisseria gonorrhoeae, and Plasmodium berghei enzymes in all three series, although somewhat different for Escherichia coli DHFR, leading to the conclusion that the hydrophobic pockets are similar for the first three isozymes. Optimal substitution was reached with 3,5-di-n-propyl or 3-ethyl-5-n-propyl groups. Branching of chains at the alpha-carbon, which resulted in increased substituent thickness, was detrimental to E. coli DHFR inhibition in particular. MR is an inadequate parameter for use in correlating such substituent effects. Conformational changes of the more bulky inhibitors can be invoked to explain some differences in inhibitory pattern. Although log P explains simple substituent effects with the vertebrate DHFRs very well, it is insufficient in the more complex cases described here, where shape is clearly involved as well. Solvent-accessible surface areas were measured for TMP in E. coli and chicken DHFRs, where the coordinates are now known. The environment is more hydrophobic in the latter case; this can also be postulated for rat DHFR, which has a very similar activity profile. As with the mammalian isozymes, N. gonorrhoeae DHFR contains an active site phenylalanine replacing Leu-28 of E. coli DHFR, thus creating a more hydrophobic pocket. A similar replacement may also occur in the P.berghei isozyme. Selectivity for bacterial DHFR is dependent on the nature of the 4-substituent, being low for polar 4-hydroxy compounds but high for polar 4-amino analogues, possibly as a result of solvation differences. With complex substituents, the environment of each atom in the active site must be taken into account to adequately explain structure-activity relationships.