(Z)-2-[2-(3,4,5-trimethoxy-phenyl)-vinyl]-thiophene | 1124219-03-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-2-[2-(3,4,5-trimethoxy-phenyl)-vinyl]-thiophene
• 英文别名: (Z)-2-(3,4,5-trimethoxystyryl)thiophene；2-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]thiophene
• CAS: 1124219-03-9
• 化学式: C₁₅H₁₆O₃S
• 分子量: 276.356
• InChiKey: RTDDXADBPBRACC-SREVYHEPSA-N

物化性质

• 沸点：
  404.8±40.0 °C(predicted)
• 密度：
  1.180±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-乙炔噻吩 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 [RuCl(CH=CHPh)(CO)(H₂IMes)(PCy₃)] 、 potassium tert-butylate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 26.0h， 生成 (Z)-2-[2-(3,4,5-trimethoxy-phenyl)-vinyl]-thiophene
  参考文献：
  名称：

  钌催化 (Z)-末端炔烃与萘-1,8-二氨基硼烷的选择性硼氢化反应

  摘要：

  由于硼氢化的通常 (E) 选择性性质和热力学不稳定 (Z) 异构体的形成，金属催化的 (Z) 选择性硼氢化反应仍然是合成挑战。在此，我们报告了空气稳定的 N-杂环-卡宾-连接的钌配合物催化末端炔烃与 HB(dan)（dan = naphthalene-1,8-diaminato）的（Z）-选择性硼氢化反应，产生多种范围具有合成价值的 (Z)-链烯基硼烷。机理研究，特别是催化相关硼基钌配合物的分离，揭示了一种涉及炔烃插入 Ru-B 键的机制，这提供了与先前报道的 (Z) 选择性硼氢化反应明显不同的催化循环.

  DOI：

  10.1021/jacs.9b06910

文献信息

• Synthesis of (Z) isomers of benzoheterocyclic derivatives of combretastatin A-4: a comparative study of several methods
  作者：Thi Thanh Binh Nguyen、Thierry Lomberget、Ngoc Chau Tran、Roland Barret

  DOI：10.1016/j.tet.2013.01.005

  日期：2013.3

  monobromoalkene, a combination of hydrosilylation/vinylsilane hydrolysis and a palladium-catalyzed semi-hydrogenation step, using DMF/KOH as the hydrogen source. Our studies led us to prepare a series of diarylacetylene derivatives via a Sonogashira coupling reaction, and also to find out a copper-free basic cyclization leading to benzo[b]thiophenes. The final choice for the synthesis method of 1 strongly depends

  研究了几种制备（Z）三甲氧基苯乙烯衍生物1的方法。在发现Wittig反应导致不满意的结果后，考虑了三种不同的策略：使用DMF / KOH作为氢源的Suzuki偶联与立体定义的单溴烯烃，氢化硅烷化/乙烯基硅烷水解和钯催化的半氢化步骤的组合。我们的研究使我们通过Sonogashira偶联反应制备了一系列二芳基乙炔衍生物，并且发现了无铜的碱性环化反应，从而生成了苯并[ b ]噻吩。1的合成方法的最终选择 强烈依赖于目标化合物，但通常应优先选择避免使用有毒锡还原剂的半氢化反应。
• 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。
• Synthesis and biological evaluation of thiophene and benzo[b]thiophene analogs of combretastatin A-4 and isocombretastatin A-4: A comparison between the linkage positions of the 3,4,5-trimethoxystyrene unit
  作者：Cong Viet Do、Abdelfattah Faouzi、Caroline Barette、Amaury Farce、Marie-Odile Fauvarque、Evelyne Colomb、Laura Catry、Odile Berthier-Vergnes、Marek Haftek、Roland Barret、Thierry Lomberget

  DOI：10.1016/j.bmcl.2015.11.010

  日期：2016.1

  Combretastatin A-4 and isocombretastatin A-4 derivatives having thiophenes or benzo[b]thiophenes instead of the B ring were prepared and evaluated for their in cellulo tubulin polymerization inhibition (TPI) and antiproliferative activities. The presence of the benzo[b]thiophene ring proved to have a crucial effect as most of the thiophene derivatives, except those having one methoxy group, were inactive to inhibit tubulin polymerization into microtubules. The influence of the attachment position was also studied: benzo[b]thiophenes having iso or cis 3,4,5-trimethoxystyrenes at position 2 were 12-30-fold more active than the 3-regioisomers for the TPI activity. Some of the novel designed compounds exhibited interesting anti-proliferative effects on two different cell lines. (C) 2015 Elsevier Ltd. All rights reserved.
• Ruthenium-Catalyzed (<i>Z</i>)-Selective Hydroboration of Terminal Alkynes with Naphthalene-1,8-diaminatoborane
  作者：Kensuke Yamamoto、Yusei Mohara、Yuichiro Mutoh、Shinichi Saito

  DOI：10.1021/jacs.9b06910

  日期：2019.10.30

  metal-catalyzed (Z)-selective hydroboration of terminal alkynes remains a synthetic challenge due to the usually (E)-selective nature of the hydroboration and the formation of the thermodynamically unstable (Z)-isomer. Herein, we report that air-stable N-heterocyclic-carbene-ligated ruthenium complexes catalyze the (Z)-selective hydroboration of terminal alkynes with H-B(dan) (dan = naphthalene-1,8-diaminato)

  由于硼氢化的通常 (E) 选择性性质和热力学不稳定 (Z) 异构体的形成，金属催化的 (Z) 选择性硼氢化反应仍然是合成挑战。在此，我们报告了空气稳定的 N-杂环-卡宾-连接的钌配合物催化末端炔烃与 HB(dan)（dan = naphthalene-1,8-diaminato）的（Z）-选择性硼氢化反应，产生多种范围具有合成价值的 (Z)-链烯基硼烷。机理研究，特别是催化相关硼基钌配合物的分离，揭示了一种涉及炔烃插入 Ru-B 键的机制，这提供了与先前报道的 (Z) 选择性硼氢化反应明显不同的催化循环.