(Z)-2-[2-(3,4,5-trimethoxy-phenyl)-vinyl]-indole-1-carboxylic acid tert-butyl ester | 1415089-11-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (Z)-2-[2-(3,4,5-trimethoxy-phenyl)-vinyl]-indole-1-carboxylic acid tert-butyl ester
• 英文别名: (Z)-1-(tert-butoxycarbonyl)-2-(3,4,5-trimethoxystyryl)-1H-indole；tert-butyl 2-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]indole-1-carboxylate
• CAS: 1415089-11-0
• 化学式: C₂₄H₂₇NO₅
• 分子量: 409.482
• InChiKey: HUISIACHXOFEQR-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  58.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-2-[2-(3,4,5-trimethoxy-phenyl)-vinyl]-indole-1-carboxylic acid tert-butyl ester 在 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 46.0h， 以28%的产率得到(Z)-2-[2-(3,4,5-trimethoxy-phenyl)-vinyl]-1H-indole
  参考文献：
  名称：

  康他汀A-4苯并杂环衍生物的（Z）异构体的合成：几种方法的比较研究

  摘要：

  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。

  DOI：

  10.1016/j.tet.2013.01.005
• 作为产物：
  描述：

  1-(Boc)-1H-吲哚-2-三氟硼酸钾 、 5-[(Z)-2-Bromoethenyl]-1,2,3-trimethoxybenzene 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 18.0h， 以47%的产率得到(Z)-2-[2-(3,4,5-trimethoxy-phenyl)-vinyl]-indole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of novel heterocyclic derivatives of combretastatin A-4

  摘要：

  A novel series of combretastatin A-4 heterocyclic analogues was prepared by replacement of the B ring with indole, benzofurane or benzothiophene, attached at the C2 position. These compounds were evaluated for their abilities to inhibit tubulin assembly: derivative cis 3b, having a benzothiophene, showed an activity similar to those of colchicine or deoxypodophyllotoxine. The antiproliferative and antimitotic properties of cis 3b against keratinocyte cancer cell lines were also evaluated and the intracellular organization of microtubules in the cells after treatment with both stereoisomers of 3b was also determined, using confocal microscopy. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.047

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。
• Synthesis and biological evaluation of novel heterocyclic derivatives of combretastatin A-4
  作者：Thi Thanh Binh Nguyen、Thierry Lomberget、Ngoc Chau Tran、Evelyne Colomb、Lore Nachtergaele、Sylviane Thoret、Joëlle Dubois、Joren Guillaume、Rawad Abdayem、Marek Haftek、Roland Barret

  DOI：10.1016/j.bmcl.2012.09.047

  日期：2012.12

  A novel series of combretastatin A-4 heterocyclic analogues was prepared by replacement of the B ring with indole, benzofurane or benzothiophene, attached at the C2 position. These compounds were evaluated for their abilities to inhibit tubulin assembly: derivative cis 3b, having a benzothiophene, showed an activity similar to those of colchicine or deoxypodophyllotoxine. The antiproliferative and antimitotic properties of cis 3b against keratinocyte cancer cell lines were also evaluated and the intracellular organization of microtubules in the cells after treatment with both stereoisomers of 3b was also determined, using confocal microscopy. (C) 2012 Elsevier Ltd. All rights reserved.