ethyl (2E,4E)-5-(2,4,6-trimethoxyphenyl)-3-methyl-2,4-pentadienoate | 64003-81-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl (2E,4E)-5-(2,4,6-trimethoxyphenyl)-3-methyl-2,4-pentadienoate
• 英文别名: ethyl (2E,4E)-5-(2,4,6-trimethoxyphenyl)-3-methylpenta-2,4-dienoate；ethyl (2E,4E)-3-methyl-5-(2,4,6-trimethoxyphenyl)penta-2,4-dienoate
• CAS: 64003-81-2
• 化学式: C₁₇H₂₂O₅
• 分子量: 306.359
• InChiKey: LIRNLDRHRCNBJM-ANKZSMJWSA-N

物化性质

• 沸点：
  454.3±45.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  ethyl (2E,4E)-5-(2,4,6-trimethoxyphenyl)-3-methyl-2,4-pentadienoate 在 N,N-二甲基丙烯基脲 、 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 正丁基锂 作用下， 生成 ethyl (2E,4E,6E,8Z,10E,12E)-13-(2,4,6-trimethoxyphenyl)-2,7,11-trimethyl-2,4,6,8,10,12-tridecahexaenoate
  参考文献：
  名称：

  Photocurrents of solar cells sensitized by aggregate-forming polyenes: Enhancement due to suppression of singlet–triplet annihilation by lowering of dye concentration or light intensity

  摘要：

  Titania-based Gratzel-type solar cells were fabricated by the use of polyene dyes with various transition dipole moments. in the dye having the largest transition dipole among the samples, an aggregate was readily formed through dispersive interaction, and the photocurrent was increased when the dye concentration or the light intensity was lowered. This observation was ascribed to the suppression of the singlet-triplet annihilation reaction. In the dye having the smallest transition dipole, there was no sign of aggregate formation, and the photocurrent was decreased when the dye concentration or the light intensity was lowered. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cplett.2006.01.003
• 作为产物：
  描述：

  3-甲基-2-丁烯酸乙酯 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 生成 ethyl (2E,4E)-5-(2,4,6-trimethoxyphenyl)-3-methyl-2,4-pentadienoate
  参考文献：
  名称：

  脱落酸芳香类似物的合成及生物学效应

  摘要：

  摘要 使用 Reformatsky 和 ​​Wittig 反应合成了 36 种不同的 3-甲基-5-芳基-2,4-戊二烯酸和酯。不同的几何异构体可以通过干柱技术方便地分离。戊二烯侧链的构型分配基于NMR和UV特性。ABA 芳香族类似物的生物活性在四种生物测定中确定。大多数类似物的活性低于天然激素。在所有四种生物测定中，只有 3-methyl-5-p-chlorophenyl Δ 2 - trans , Δ 4 - trans -pentadienoic acid 表现出高 ABA 样活性。

  DOI：

  10.1016/s0031-9422(00)94349-8

文献信息

• Syntheses, antiproliferative activity and theoretical characterization of acitretin-type retinoids with changes in the lipophilic part
  作者：George E. Magoulas、Stavros E. Bariamis、Constantinos M. Athanassopoulos、Anastasios Haskopoulos、Petros G. Dedes、Marios G. Krokidis、Nikos K. Karamanos、Dimitris Kletsas、Dionissios Papaioannou、George Maroulis

  DOI：10.1016/j.ejmech.2010.12.008

  日期：2011.2

  Acitretin analogs, incorporating changes in the lipophilic part, were efficiently synthesized from commercially available aromatic aldehydes or methyl ketones using the Wittig or Horner-Wadsworth-Emmons reaction. Their antiproliferative activity was evaluated against human breast MCF-7 epithelial cells. Analogs 3, 4, 8 and 11 exhibited strong, dose-dependent, antiproliferative activity on the tested cell line. Analog 3, incorporating three methoxy groups in the aromatic ring, exhibited the strongest inhibitory effect at 10 mu M. High-level all electron conventional ab initio and density functional theory quantum chemical calculations were performed to obtain the molecular structure, electron charge distribution and polarization properties of all compounds of interest in this work. The most active analogs were planar and were characterized by larger dipole moments than the other synthesized molecules. Another factor of importance to the analysis of the activity of these molecules is the dipole polarizability. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Photocurrents of solar cells sensitized by aggregate-forming polyenes: Enhancement due to suppression of singlet–triplet annihilation by lowering of dye concentration or light intensity
  作者：Xiao-Feng Wang、Yasushi Koyama、Hiroyoshi Nagae、Yumiko Yamano、Masayoshi Ito、Yuji Wada

  DOI：10.1016/j.cplett.2006.01.003

  日期：2006.3

  Titania-based Gratzel-type solar cells were fabricated by the use of polyene dyes with various transition dipole moments. in the dye having the largest transition dipole among the samples, an aggregate was readily formed through dispersive interaction, and the photocurrent was increased when the dye concentration or the light intensity was lowered. This observation was ascribed to the suppression of the singlet-triplet annihilation reaction. In the dye having the smallest transition dipole, there was no sign of aggregate formation, and the photocurrent was decreased when the dye concentration or the light intensity was lowered. (c) 2006 Elsevier B.V. All rights reserved.
• Synthesis and biological effects of aromatic analogs of abscisic acid
  作者：Shmuel Bittner、Malka Gorodetsky、Irit Har-Paz、Yosef Mizrahi、Amos E. Richmond

  DOI：10.1016/s0031-9422(00)94349-8

  日期：1977.1

  six different 3-methyl-5-aryl-2,4-pentadienoic acids and esters were synthesized using the Reformatsky and Wittig reactions. The different geometrical isomers were conveniently separated by the dry column technique. Assignment of configuration of the pentadienoic side chain was based on NMR and UV properties. The biological activities of the aromatic analogs of ABA were determined in four bioassays

  摘要 使用 Reformatsky 和 ​​Wittig 反应合成了 36 种不同的 3-甲基-5-芳基-2,4-戊二烯酸和酯。不同的几何异构体可以通过干柱技术方便地分离。戊二烯侧链的构型分配基于NMR和UV特性。ABA 芳香族类似物的生物活性在四种生物测定中确定。大多数类似物的活性低于天然激素。在所有四种生物测定中，只有 3-methyl-5-p-chlorophenyl Δ 2 - trans , Δ 4 - trans -pentadienoic acid 表现出高 ABA 样活性。