1,2,3-trimethoxy-5-[(E)-2-(4-methylphenyl)ethenyl]benzene | 141172-18-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,2,3-trimethoxy-5-[(E)-2-(4-methylphenyl)ethenyl]benzene
• 英文别名: (E)-1-(4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)ethene；(E)-3,4,5-trimethoxy-4'-methylstilbene；3,4,5-trimethoxy-4'-methylstilbene；(E)-(4-Methylphenyl)-2-(3,4,5-trimethoxyphenyl)ethene；(E) 3,5-Trimethoxy-4'-methylstilbene
• CAS: 141172-18-1
• 化学式: C₁₈H₂₀O₃
• 分子量: 284.355
• InChiKey: YSJFPRSDNPCGBF-MDZDMXLPSA-N

物化性质

• 熔点：
  125-127 °C
• 沸点：
  414.3±40.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2,3-trimethoxy-5-[(E)-2-(4-methylphenyl)ethenyl]benzene 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以45%的产率得到5-[(E)-2-[4-(bromomethyl)phenyl]ethenyl]-1,2,3-trimethoxybenzene
  参考文献：
  名称：

  具有分离的芪生色团的树枝状聚合物的制备和光化学

  摘要：

  除了模型化合物 4a 和 4b 之外，还制备了在核心和树枝外围具有反式二苯乙烯发色团的树枝状聚合物 11 和 14，并在溶液和纯薄膜中研究了它们的光化学。由于臂的柔韧性，在辐照时会形成分子内和分子间 CC 键。因此，代表小的低聚物的纳米颗粒的产生比刚性、交叉共轭的二苯乙烯树状大分子的交联更有可能。紫外和核磁共振光谱研究了溶液中的光反应，原子力显微镜研究了薄膜的转变。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  DOI：

  10.1002/ejoc.200500185
• 作为产物：
  描述：

  4-甲基氯苄 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 1,2,3-trimethoxy-5-[(E)-2-(4-methylphenyl)ethenyl]benzene
  参考文献：
  名称：

  Synthesis and Optical Properties of Polystyrene Bearing Stilbenoid Side Chains

  摘要：

  Four series of random graft copolymers with stilbenoid side chains on a polystyrene (PS) backbone were synthesized, and their optical properties were compared with blends of a series of model compounds in PS. The graft loading (5, 15, and 25 mol %), the type of link to the polymer backbone ("ether" or "direct"), and the number of methoxy groups substituted on the stilbene moiety were systematically varied. Absorption, emission, and time-resolved photoluminescence (PL) properties are presented for the compounds in solution and as spin-coated films, and relative quantum yields have been determined. Mixed monomer/excimer emission was found to be the characteristic emission for all grafts, while the reversibility of the excimer formation seems to vary for the different grafts. In the blends the miscibility of the model compounds is quite different: the 4-methoxystilbene/PS system readily forms aggregates and crystallites, whereas the 3,4,5-trimethoxy-4'-methylstilbene/PS system forms uniform mixtures showing excimer-type emission. The PL efficiencies decreased with concentration in all cases where excimeric emission was found. For the blend containing 4-methoxystilbene, however, the PL efficiency increased with concentration.

  DOI：

  10.1021/ma035632v

文献信息

• Diastereodivergent Reductive Cross Coupling of Alkynes through Tandem Catalysis: <i>Z</i>- and <i>E</i>-Selective Hydroarylation of Terminal Alkynes
  作者：Megan K. Armstrong、Madison B. Goodstein、Gojko Lalic

  DOI：10.1021/jacs.8b05113

  日期：2018.8.15

  diastereodivergent hydroarylation of terminal alkynes is accomplished using tandem catalysis. The hydroarylation allows highly selective synthesis of both E and Z diastereoisomers of aryl alkenes, from the same set of starting materials, using the same combination of palladium and copper catalysts. The selectivity is controlled by simple changes in the stoichiometry of the alcohol additive. The hydroarylation has

  使用串联催化完成末端炔烃的非对映发散加氢芳基化。加氢芳基化允许使用相同的钯和铜催化剂组合，从同一组起始材料高度选择性地合成芳基烯烃的E和Z非对映异构体。通过简单改变醇添加剂的化学计量来控制选择性。加氢芳基化具有优异的底物范围，并且可以在各种化合物存在下完成，包括酯、腈、卤代烷、环氧化物、氨基甲酸酯、缩醛、醚、甲硅烷基醚和硫醚。 Z-选择性加氢芳基化是使用基于串联 Sonogashira 偶联和催化半还原的新方法完成的。 E-选择性加氢芳基化涉及Z-烯烃的额外催化异构化。我们对反应机制的探索解释了各个反应组分的作用以及反应条件的微妙变化如何影响加氢芳基化的特定步骤的速率。我们的研究还表明，虽然Z-和E-选择性加氢芳基化反应在机理上密切相关，但钯和铜催化剂在这两个反应中的作用是不同的。
• Synthesis and evaluation of analogs of (Z)-1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene as potential cytotoxic and antimitotic agents
  作者：Mark Cushman、Dhanapalan Nagarathnam、D. Gopal、Hu Ming He、Chii M. Lin、Ernest Hamel

  DOI：10.1021/jm00090a021

  日期：1992.6

  1a resembles that of the cis alkene 1. Additional inactive compounds prepared include the benzylisoquinoline series 28-32 as well as the protoberberines 38 and 39. Shortening the two-carbon bridge of 1a to a one-carbon bridge in the diphenylmethane 20 resulted in a decrease in cytotoxicity and tubulin polymerization inhibitory activity. Although the corresponding benzophenone 18 was as active as 1a as

  已经制备了一系列对苯二酚，并在五种人类癌细胞系A-549非小细胞肺癌，MCF-7乳腺癌，HT-29结肠癌，SKMEL-5黑色素瘤和MLM黑色素瘤中测试了细胞毒性。顺式斯蒂芬斯6a-f在所有五个细胞系中均被证明具有细胞毒性，其效力可与康美他汀A-4媲美。这些细胞毒性化合物都是微管蛋白聚合的有效抑制剂。相应的反丁苯橡胶7b-f作为微管蛋白聚合抑制剂没有活性，并且在5种癌细胞系中的细胞毒性明显较小。在二氢系列中，8b，8c和8f作为微管蛋白聚合抑制剂没有活性，而8a，8d和8e的活性低于相应的顺式化合物6a，6d和6e。菲23b缺乏对微管蛋白聚合的抑制活性和细胞毒性，作为前导化合物1的构象刚性类似物合成的Silbenes的活性表明，斯蒂芬酯的活性不是由于完全平面的构象。同样，构象受限的类似物26的无活性表明1a的生物活性构象与顺式烯烃1相似。制备的其他无活性化合物包括苄基异喹啉系列28-32以及
• Preparation and Photochemistry of Dendrimers with Isolated Stilbene Chromophores
  作者：Shahid A. Soomro、Reda Benmouna、Rüdiger Berger、Herbert Meier

  DOI：10.1002/ejoc.200500185

  日期：2005.8

  In addition to the model compounds 4a and 4b, the dendrimers 11 and 14 with trans-stilbene chromophores in the core and on the periphery of the dendrons were prepared and their photochemistry was studied in solution and in neat films. Due to the flexibility of the arms, intramolecular and intermolecular CC bonds are formed on irradiation. Thus, the generation of nanoparticles, which represent small

  除了模型化合物 4a 和 4b 之外，还制备了在核心和树枝外围具有反式二苯乙烯发色团的树枝状聚合物 11 和 14，并在溶液和纯薄膜中研究了它们的光化学。由于臂的柔韧性，在辐照时会形成分子内和分子间 CC 键。因此，代表小的低聚物的纳米颗粒的产生比刚性、交叉共轭的二苯乙烯树状大分子的交联更有可能。紫外和核磁共振光谱研究了溶液中的光反应，原子力显微镜研究了薄膜的转变。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• An Efficient Microwave-Promoted Route to (Z)-Stilbenes from trans-Cinnamic Acids: Synthesis of Combretastatin A-4 and Analogues
  作者：Sylvain Rault、Marc-Antoine Bazin、Marie Jouanne、Hussein El-Kashef

  DOI：10.1055/s-0029-1217981

  日期：2009.10

  cis-Stilbenes were synthesized from trans-cinnamic acids, involving ethylenic-bond bromination and a subsequent one-pot microwave-promoted stereoselective debrominative decarboxylation-Suzuki cross-coupling strategy. This sequence represents a useful way to prepare a variety of combretastatin A-4 derivatives.

  顺式二苯乙烯由反式肉桂酸合成，涉及烯键溴化和随后的一锅微波促进立体选择性脱溴脱羧-铃木交叉偶联策略。该序列代表了制备多种考布他汀 A-4 衍生物的有用方法。
• Efficient synthesis of benzylphosphine oxides and E-stilbenes
  作者：Karen M. Brown、Nicholas J. Lawrence、John Liddle、Faiz Muhammad、David A. Jackson

  DOI：10.1016/s0040-4039(00)73481-2

  日期：1994.9

  A series of substituted benzylphosphine oxides has been synthesised by reduction of the corresponding (alpha-chlorobenzyl)phosphine oxide, derived from the benzaldehyde and chlorodiphenylphosphine, with either sodium borohydride (DMSO, 60-70 degrees C, 12 h) or tributyltin hydride and AIBN (C6H6. 80 degrees C, 2 h). Reaction of the (alpha-lithiobenzyl)phosphine oxide with aldehydes gave exclusively E-alkenes.