1-(3-tert-butyldimethylsilyloxy-4-methoxyphenyl)-2,2-dibromoethene | 388566-83-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(3-tert-butyldimethylsilyloxy-4-methoxyphenyl)-2,2-dibromoethene
• 英文别名: 1-(3'-t-Butyldimethylsilyloxy-4'-methoxyphenyl)-2,2-dibromoethene；tert-butyl-[5-(2,2-dibromoethenyl)-2-methoxyphenoxy]-dimethylsilane
• CAS: 388566-83-4
• 化学式: C₁₅H₂₂Br₂O₂Si
• 分子量: 422.232
• InChiKey: HCECWPQTWKVMCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.17
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-tert-butyldimethylsilyloxy-4-methoxyphenyl)-2,2-dibromoethene 在 四(三苯基膦)钯 吡啶 、 四(三苯基膦)钯 、 四丁基氟化铵 、 三正丁基氢锡 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 苯 为溶剂， 反应 0.33h， 生成 (Z)-3,4,5,4',-四甲氧基-3'-羟基二苯乙烯
  参考文献：
  名称：

  Novel Syntheses of Cis and Trans Isomers of Combretastatin A-4

  摘要：

  A high-yielding, two-step stereoselective synthesis of the anticancer drug (Z)-combretastatin A-4 (1) has been devised. The method uses the Perkin condensation of 3,4,5-trimethoxyphenylacetic acid and 3-hydroxy-4-methoxybenzaldehyde followed by decarboxylation of the cinnamic acid intermediate using copper and quinoline. The iodine-catalyzed isomerization of the Z isomer 1 results in complete conversion to the E isomer. The Suzuki cross-coupling of an aryl boronic acid and vinyl bromide has also been successfully employed to produce both Z and E isomers of combretastatin A-4 stereoselectively. Both methods are far superior to the current five-step Wittig synthesis in which both isomers are produced nonstereoselectively.

  DOI：

  10.1021/jo015959z
• 作为产物：
  描述：

  异香兰素 在 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.33h， 生成 1-(3-tert-butyldimethylsilyloxy-4-methoxyphenyl)-2,2-dibromoethene
  参考文献：
  名称：

  Novel Syntheses of Cis and Trans Isomers of Combretastatin A-4

  摘要：

  A high-yielding, two-step stereoselective synthesis of the anticancer drug (Z)-combretastatin A-4 (1) has been devised. The method uses the Perkin condensation of 3,4,5-trimethoxyphenylacetic acid and 3-hydroxy-4-methoxybenzaldehyde followed by decarboxylation of the cinnamic acid intermediate using copper and quinoline. The iodine-catalyzed isomerization of the Z isomer 1 results in complete conversion to the E isomer. The Suzuki cross-coupling of an aryl boronic acid and vinyl bromide has also been successfully employed to produce both Z and E isomers of combretastatin A-4 stereoselectively. Both methods are far superior to the current five-step Wittig synthesis in which both isomers are produced nonstereoselectively.

  DOI：

  10.1021/jo015959z

文献信息

• Conjugation of Hydroxytyrosol with Other Natural Phenolic Fragments: From Waste to Antioxidants and Antitumour Compounds
  作者：Erika Tassano、Angela Alama、Andrea Basso、Giancarlo Dondo、Andrea Galatini、Renata Riva、Luca Banfi

  DOI：10.1002/ejoc.201500931

  日期：2015.10

  Hydroxytyrosol, a natural polyphenol that can be extracted from olive mill waste waters, was converted into a series of more complex and lipophilic analogues by conjugation with other naturally derived (poly)phenolic fragments. Ether and triazole linkers were employed. A small library of compounds was prepared, stressing step economy and operational simplicity. Some of these substances were proven

  羟基酪醇是一种可以从橄榄厂废水中提取的天然多酚，通过与其他天然衍生的（多）酚类片段结合，转化为一系列更复杂和亲脂的类似物。使用醚和三唑接头。准备了一个小型化合物库，强调步骤经济和操作简单。在自由基清除试验以及对肿瘤细胞的细胞毒性试验中，这些物质中的一些被证明具有与母体羟基酪醇相同或优于母体羟基酪醇的活性。
• Synthesis and biological evaluation of vinylogous combretastatin A-4 derivatives
  作者：Julia Kaffy、Renée Pontikis、Jean-Claude Florent、Claude Monneret

  DOI：10.1039/b505955k

  日期：——

  Stereospecific syntheses of the Z–E and E–Z vinylogues of combretastatin A-4, and two B-ring related analogues, were achieved through a Suzuki–Miyaura coupling. As compared to CA4, the derivative with a phenyl moiety has shown increased potency in its ability to inhibit tubulin polymerisation.

  通过铃木–宫浦耦合实现了Z–E和E–Z的康柏塔斯汀A-4的醇类化合物的立体特异合成，以及两个与B环相关的类似物。与CA4相比，含有苯基部分的衍生物在抑制微管聚合的能力上显示出更强的效 potency。
• Materials and methods for synthesizing stilbenes
  申请人：——

  公开号：US20040143023A1

  公开（公告）日：2004-07-22

  The present invention relates materials and methods for synthesizing stilbenes, and in particular to processes for the synthesis of substituted stilbenes such as combretastatin A4. The present invention relates in particular to methods which are stereoselective for either the cis or the trans isomer of the substituted stilbene, using a Perkin-type condensation of an arylacetic acid and a substituted benzaldehyde, followed by a decarboxylation reaction to produce the substituted cis-stilbenes or a Suzuki-type reaction involving a Z or E-ethenyl halide and a substituted boronic acid in the presence of a palladium catalyst to produce specifically either the Z or E-isomer of substituted stilbenes.

  本发明涉及合成苯乙烯类物质的材料和方法，特别是用于合成取代苯乙烯类物质如结合静脉A4的过程。本发明特别涉及具有对取代苯乙烯类物质的顺反异构体具有立体选择性的方法，包括使用苯乙酸芳基和取代苯甲醛的Perkin型缩合反应，随后进行脱羧反应以产生取代顺式苯乙烯或涉及Z或E-乙烯基卤化物和取代硼酸在钯催化剂存在下的Suzuki型反应，以特别产生Z或E-取代苯乙烯的异构体。
• Novel Syntheses of Cis and Trans Isomers of Combretastatin A-4
  作者：Keira Gaukroger、John A. Hadfield、Lucy A. Hepworth、Nicholas J. Lawrence、Alan T. McGown

  DOI：10.1021/jo015959z

  日期：2001.11.1

  A high-yielding, two-step stereoselective synthesis of the anticancer drug (Z)-combretastatin A-4 (1) has been devised. The method uses the Perkin condensation of 3,4,5-trimethoxyphenylacetic acid and 3-hydroxy-4-methoxybenzaldehyde followed by decarboxylation of the cinnamic acid intermediate using copper and quinoline. The iodine-catalyzed isomerization of the Z isomer 1 results in complete conversion to the E isomer. The Suzuki cross-coupling of an aryl boronic acid and vinyl bromide has also been successfully employed to produce both Z and E isomers of combretastatin A-4 stereoselectively. Both methods are far superior to the current five-step Wittig synthesis in which both isomers are produced nonstereoselectively.