(Z)-5-(2'-bromoethenyl)-2-methoxyphenol | 388566-84-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (Z)-5-(2'-bromoethenyl)-2-methoxyphenol
• 英文别名: 5-(2-bromo-vinyl)-2-methoxy-phenol；Methyl-[2-hydroxy-4-(2-brom-vinyl)-phenyl]-aether；β-Brom-3-hydroxy-4-methoxy-styrol；5-(2-Brom-vinyl)-2-methoxy-phenol；Z-5-(2-Bromo-ethenyl)-2-methoxy-phenol；5-[(Z)-2-bromoethenyl]-2-methoxyphenol
• CAS: 388566-84-5
• 化学式: C₉H₉BrO₂
• 分子量: 229.073
• InChiKey: INVFXCLNDAHVLR-PLNGDYQASA-N

物化性质

• 沸点：
  347.5±32.0 °C(Predicted)
• 密度：
  1.532±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-5-(2'-bromoethenyl)-2-methoxyphenol 在 四(三苯基膦)钯 、 碘 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 氯仿 为溶剂， 反应 0.5h， 生成 trans-combretastatin A-4
  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：

  异阿魏酸 在 溴 、 溶剂黄146 作用下， 生成 (Z)-5-(2'-bromoethenyl)-2-methoxyphenol
  参考文献：
  名称：

  Schoepf et al., Justus Liebigs Annalen der Chemie, 1940, vol. 544, p. 30,58

  摘要：

  DOI：

文献信息

• 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stilbenes的材料和方法，特别是用于合成取代stilbenes（如combretastatin A4）的过程。本发明特别涉及对取代stilbene的顺式或反式异构体具有立体选择性的方法，其中使用芳基乙酸和取代苯甲醛的Perkin型缩合，随后进行脱羧反应以产生取代顺式stilbenes，或者涉及在钯催化剂存在下使用Z或E-乙烯卤代物和取代硼酸进行Suzuki型反应，以特异性地产生Z或E异构体的取代stilbenes。
• MATERIALS AND METHODS FOR SYNTHESIZING STILBENES
  申请人：Cancer Research Ventures Limited

  公开号：EP1351911A2

  公开（公告）日：2003-10-15
• [EN] MATERIALS AND METHODS FOR SYNTHESIZING STILBENES<br/>[FR] SUBSTANCES ET METHODES DE SYNTHESE DE STILBENES
  申请人：CANCER RES VENTURES LTD

  公开号：WO2002049994A2

  公开（公告）日：2002-06-27

  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.
• 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.