(E,E)-3,5-Bis[2-(3,4,5-trihexyloxyphenyl)ethenyl]benzaldehyde | 296795-94-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (E,E)-3,5-Bis[2-(3,4,5-trihexyloxyphenyl)ethenyl]benzaldehyde
• 英文别名: 3,5-bis[(E)-2-(3,4,5-trihexoxyphenyl)ethenyl]benzaldehyde
• CAS: 296795-94-3
• 化学式: C₅₉H₉₀O₇
• 分子量: 911.359
• InChiKey: FYDPRMGDGQRNRI-FMWAKIAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.8
• 重原子数：
  66
• 可旋转键数：
  41
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,3,5-tris(diethoxyphosphorylmethyl)benzene 、 (E,E)-3,5-Bis[2-(3,4,5-trihexyloxyphenyl)ethenyl]benzaldehyde 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以71%的产率得到all-(E)-1,3,5-Tris{2-{3,5-bis[2-(3,4,5-trihexyloxyphenyl)ethenyl]phenyl}ethenyl}benzene
  参考文献：
  名称：

  Stilbenoid Dendrimers

  摘要：

  The first five generations of the stilbenoid dendrimers 1(n) (n = 1-5) have been prepared by a combined coupled synthesis (between the generations of the dendrons 8-12) and convergent synthesis. Wittig-Horner reactions together with a protecting group technique yield monodisperse compounds of high constitutional and configurational purity. The solubility of the stiff molecules, which have primarily a disklike shape in the first and second generations and a cylindrical shape in the third, fourth, and fifth generations, is governed by the alkoxy chains that are attached to the peripheral benzene rings. The number of stilbene building blocks increases according to the formula 3(2(n)-1) from 3 in the first generation (n = 1) to 93 in the fifth generation (n = 5). Consequently, the molecular mass reaches 24,000 in 1(5)b which contains 144 hexyloxy chains. An exact measurement of the mass is provided by matrix-assisted laser desorption ionization time-of-flight (MALDI-TOF) mass spectrometry. In solution, the stilbenoid dendrimers 1(n) exhibit a strong tendency to aggregate, which increases from generation to generation. In the pure state, columnar mesophases Col(hd) (1(1)b, 1(1)c, 1(2)b, and 1(2)c) and Col(ob) (1(2)b, 1(2)c) are formed; intramolecular steric hindrance prevents such ordered arrangements in higher generations 1(n) (n = 3, 4, 5).

  DOI：

  10.1002/1521-3765(20000703)6:13<2462::aid-chem2462>3.0.co;2-a
• 作为产物：
  描述：

  在 盐酸 作用下， 以 氯仿 为溶剂， 反应 12.0h， 生成 (E,E)-3,5-Bis[2-(3,4,5-trihexyloxyphenyl)ethenyl]benzaldehyde
  参考文献：
  名称：

  Stilbenoid Dendrimers

  摘要：

  The first five generations of the stilbenoid dendrimers 1(n) (n = 1-5) have been prepared by a combined coupled synthesis (between the generations of the dendrons 8-12) and convergent synthesis. Wittig-Horner reactions together with a protecting group technique yield monodisperse compounds of high constitutional and configurational purity. The solubility of the stiff molecules, which have primarily a disklike shape in the first and second generations and a cylindrical shape in the third, fourth, and fifth generations, is governed by the alkoxy chains that are attached to the peripheral benzene rings. The number of stilbene building blocks increases according to the formula 3(2(n)-1) from 3 in the first generation (n = 1) to 93 in the fifth generation (n = 5). Consequently, the molecular mass reaches 24,000 in 1(5)b which contains 144 hexyloxy chains. An exact measurement of the mass is provided by matrix-assisted laser desorption ionization time-of-flight (MALDI-TOF) mass spectrometry. In solution, the stilbenoid dendrimers 1(n) exhibit a strong tendency to aggregate, which increases from generation to generation. In the pure state, columnar mesophases Col(hd) (1(1)b, 1(1)c, 1(2)b, and 1(2)c) and Col(ob) (1(2)b, 1(2)c) are formed; intramolecular steric hindrance prevents such ordered arrangements in higher generations 1(n) (n = 3, 4, 5).

  DOI：

  10.1002/1521-3765(20000703)6:13<2462::aid-chem2462>3.0.co;2-a

文献信息

• Dendritic Triphenylmethylium and Tetraphenylmethane Compounds
  作者：Herbert Meier、Soungkyoo Kim、Annette Oehlhof

  DOI：10.1055/s-0028-1083374

  日期：——

  from the low-field shifts of the ¹³C NMR signals. In contrast to the dark-blue dyes 3′a-c, the tris(stilbenyl)carbinols and tetrakis(stilbenyl)methane derivatives 3a-c and 7 exhibit long-wavelength absorption bands in the UV region. stilbene - charge delocalization - Wittig-Horner reaction - olefination - dendrimers - dyes

  使用Wittig-Horner反应制备具有甲醇或甲烷核的Stilbenoid树状聚合物。在用三氟乙酸或四氟硼酸处理时，将树枝状三（二苯乙烯基）甲醇3a - c转化为相应的甲基盐3'a - c。树枝状亚甲基离子3'c中扩展的交叉共轭导致长波长吸收（λmax = 697 nm），而共轭模型系统3'a和3'b被红移（λmax = 772 nm和分别为748 nm）。在阳离子电荷离域从的低场位移是明显¹³C NMR信号。与深蓝色染料3'a - c相反，三（二苯乙烯基）甲醇和四（二苯乙烯基）甲烷衍生物3a - c和7在UV区域中显示出长波长吸收带。 sti-电荷离域-Wittig-Horner反应-烯烃化-树状聚合物-染料
• Stilbenoid Dendrimers
  作者：Herbert Meier、Matthias Lehmann、Ute Kolb

  DOI：10.1002/1521-3765(20000703)6:13<2462::aid-chem2462>3.0.co;2-a

  日期：2000.7.3

  The first five generations of the stilbenoid dendrimers 1(n) (n = 1-5) have been prepared by a combined coupled synthesis (between the generations of the dendrons 8-12) and convergent synthesis. Wittig-Horner reactions together with a protecting group technique yield monodisperse compounds of high constitutional and configurational purity. The solubility of the stiff molecules, which have primarily a disklike shape in the first and second generations and a cylindrical shape in the third, fourth, and fifth generations, is governed by the alkoxy chains that are attached to the peripheral benzene rings. The number of stilbene building blocks increases according to the formula 3(2(n)-1) from 3 in the first generation (n = 1) to 93 in the fifth generation (n = 5). Consequently, the molecular mass reaches 24,000 in 1(5)b which contains 144 hexyloxy chains. An exact measurement of the mass is provided by matrix-assisted laser desorption ionization time-of-flight (MALDI-TOF) mass spectrometry. In solution, the stilbenoid dendrimers 1(n) exhibit a strong tendency to aggregate, which increases from generation to generation. In the pure state, columnar mesophases Col(hd) (1(1)b, 1(1)c, 1(2)b, and 1(2)c) and Col(ob) (1(2)b, 1(2)c) are formed; intramolecular steric hindrance prevents such ordered arrangements in higher generations 1(n) (n = 3, 4, 5).