5-(2',2'-dibromoethenyl)-2-methoxyphenol | 388566-82-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-(2',2'-dibromoethenyl)-2-methoxyphenol
• 英文别名: 5-(2',2'-dibromo-ethenyl)-2-methoxyphenol；5-(2,2-dibromovinyl)-2-methoxyphenol；5-(2,2-dibromoethenyl)-2-methoxyphenol
• CAS: 388566-82-3
• 化学式: C₉H₈Br₂O₂
• 分子量: 307.969
• InChiKey: ZFWHDBGSDJRENN-UHFFFAOYSA-N

物化性质

• 沸点：
  378.3±42.0 °C(Predicted)
• 密度：
  1.895±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 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：

  5-(2',2'-dibromoethenyl)-2-methoxyphenol 在 四(三苯基膦)钯 吡啶 、 四(三苯基膦)钯 、 三正丁基氢锡 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 苯 为溶剂， 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：

  3-叔-丁基二甲基硅氧基-4-甲氧基苯甲醛 在 四丁基氟化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.66h， 生成 5-(2',2'-dibromoethenyl)-2-methoxyphenol
  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

• DBU-Mediated Efficient Synthesis of Diaryl Ethynes and Enynes from 1,1-Dibromoalkenes at Room Temperature
  作者：Yadagiri Thummala、Ashok K. Morri、Galla V. Karunakar、Venkata Ramana Doddi

  DOI：10.1002/ejoc.201801143

  日期：2018.12.6

  The DBU plays a triple role as base, nucleophile and ligand in the synthesis of internal alkynes from 1,1‐dibromoalkenes at ambient temperature.

  在环境温度下，DBU在由1,1-二溴代烯烃合成内部炔烃中，起着碱基，亲核试剂和配体的三重作用。
• 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。
• Structural Elucidation and Total Synthesis of Three 9-Norlignans from <i>Curculigo capitulata</i>
  作者：Song Li、Jin-Hai Yu、Yao-Yue Fan、Qun-Fang Liu、Zhan-Chao Li、Zhi-Xiang Xie、Ying Li、Jian-Min Yue

  DOI：10.1021/acs.joc.9b00170

  日期：2019.5.3

  three unprecedented 9-norlignans featuring a unique 3,5-dihydrofuro[2,3-d]oxepin-7(2H)-one scaffold, were isolated from the roots of Curculigo capitulata. Their structures with absolute configurations were unambiguously established by a combination of spectroscopic data, ECD analysis, and total synthesis. Biomimetic total syntheses of three pairs of the corresponding enantiomers were achieved in 9–10

  Capitulactones A–C是三个前所未有的9-norlignans，具有独特的3,5-dihydrofuro [2,3- d ] oxepin-7（2 H）-one支架，是从Curculigo capitulata的根部分离得到的。通过光谱数据，ECD分析和总合成的结合，可以明确地确定其具有绝对构型的结构。三对相应的对映异构体的仿生总合成以9-10个步骤完成，总收率分别为14.8％，12.7％和10.3％。值得注意的是，分子的共同西半球的独特支架是通过使用苯并二氢呋喃的氧化还原策略构建的。
• METHOXYIMINO COMPOUNDS AND FUNGICIDE COMPOSITION COMPRISING SAME
  申请人：Kim Joo-Kyung

  公开号：US20100298593A1

  公开（公告）日：2010-11-25

  The present invention provides a methoxyimino compound, and a fungicide composition comprising same as an active ingredient. The methoxyimino compound of the present invention, which has an excellent antifungal activity against a wide spectrum of fungi even at a low application rate, can be used to protect various crops.

  本发明提供了一种甲氧基亚胺化合物以及包含其作为活性成分的杀菌剂组合物。本发明的甲氧基亚胺化合物具有出色的抗真菌活性，即使在低施用量下也能对广谱菌类进行保护，可用于保护各种作物。