(E/Z)-ethyl 2-azido-3-(3,4-dimethoxyphenyl)acrylate | 911301-33-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E/Z)-ethyl 2-azido-3-(3,4-dimethoxyphenyl)acrylate
• 英文别名: α-Azido-3.4-dimethoxy-zimtsaeure-aethylester；ethyl 2-azido-3-(3,4-dimethoxyphenyl)prop-2-enoate
• CAS: 911301-33-2
• 化学式: C₁₃H₁₅N₃O₄
• 分子量: 277.28
• InChiKey: VYDNUFLEALWEFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  93.52
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E/Z)-ethyl 2-azido-3-(3,4-dimethoxyphenyl)acrylate 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 ethyl N-tert-butoxycarbonyl-3,4-dimethoxyphenylalaninate
  参考文献：
  名称：

  Synthesis of Phenylalanine Analogs

  摘要：

  A straightforward synthesis of phenylalanine analogs is described. Cerium ammonium nitrate (CAN) mediated addition of azide to cinnamic ester, followed by reaction with sodium acetate afforded the alpha-azidocinnamate in moderate yield. Hydrogenation of alpha-azidocinnamate, followed by BOC, CBZ or Fmoc protection gave phenylalanine analogs. A new approach for synthesizing racemic p-boronophenylalanine analog was also explored.

  DOI：

  10.1002/jccs.200500150
• 作为产物：
  描述：

  ethyl (E)-3,4-dimethoxycinnamate 在 sodium azide 、 ammonium cerium(IV) nitrate 、 sodium acetate 作用下， 以 乙腈 、 丙酮 为溶剂， 以66%的产率得到(E/Z)-ethyl 2-azido-3-(3,4-dimethoxyphenyl)acrylate
  参考文献：
  名称：

  Synthesis of Phenylalanine Analogs

  摘要：

  A straightforward synthesis of phenylalanine analogs is described. Cerium ammonium nitrate (CAN) mediated addition of azide to cinnamic ester, followed by reaction with sodium acetate afforded the alpha-azidocinnamate in moderate yield. Hydrogenation of alpha-azidocinnamate, followed by BOC, CBZ or Fmoc protection gave phenylalanine analogs. A new approach for synthesizing racemic p-boronophenylalanine analog was also explored.

  DOI：

  10.1002/jccs.200500150

文献信息

• Structural influence of indole C5-N-substitutents on the cytotoxicity of seco-duocarmycin analogs
  作者：Taeyoung Choi、Eunsook Ma

  DOI：10.1007/s12272-011-0302-1

  日期：2011.3

  A series of racemic indole C5-substituted seco-cyclopropylindoline compounds (2,3 and 5–7) were prepared by coupling 1-(tert-butyloxycarbonyl)-3-(chlorocarbonyl)indoline (seg-A) with 5,6,7-trimethoxy-, 5,6-dimethoxy-, 5-amino-, 5-methylsulfonylamino- and 5-(N,N-dimethylaminosulfonylamino) indole-2-carboxylic acid as seg-B in the presence of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide. The synthetic compounds (2,3 and 5–7) were tested for cytotoxic activity against human cancer cell lines (COLO 205, SK-MEL-2, A549, and JEG-3) using the MTT assay.

  在 1-乙基-3-(3-二甲氨基丙基)碳二亚胺的存在下，将 1-(叔丁氧羰基)-3-(氯羰基)吲哚啉（sEG-A）与 5,6,7-三甲氧基-、5,6-二甲氧基-、5-氨基-、5-甲磺酰氨基-和 5-(N,N-二甲氨基磺酰氨基)吲哚-2-羧酸（sEG-B）偶联制备。采用 MTT 法测试了合成化合物（2、3 和 5-7）对人类癌细胞株（COLO 205、SK-MEL-2、A549 和 JEG-3）的细胞毒性活性。
• Catalyst-Free Preparation of 1,2,4,5-Tetrasubstituted Imidazoles from a Novel Unexpected Domino Reaction of 2-Azido Acrylates and Nitrones
  作者：Bao Hu、Zhao Wang、Ning Ai、Jie Zheng、Xing-Hai Liu、Shang Shan、Zhongwen Wang

  DOI：10.1021/ol202650z

  日期：2011.12.16

  A highly efficient and convenient method for the synthesis of 1,2,4,5-tetrasubstituted imidazoles from readily accessible 2-azido acrylates and nitrones has been developed. This reaction proceeded under mild conditions without the assistance of any metal, acid, or base.

  已经开发了一种由容易获得的2-叠氮基丙烯酸酯和硝酮合成1,2,4,5-四取代的咪唑的高效便捷的方法。该反应在温和条件下进行，无需任何金属，酸或碱的辅助。
• One-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles by a tandem three-component reaction of hydroxylamines, aldehydes and 2-azido acrylates
  作者：Bao Hu、Ning Ai、Zhao Wang、Xiaoliang Xu、Xiaonian Li

  DOI：10.3998/ark.5550190.0013.621

  日期：——

  The reaction of nitrones, formed in situ by reaction of hydroxylamines and aldehydes, with 2azido acrylates results in the formation of 1,2,4,5-tetrasubstituted imidazoles has been developed. This three-component reaction allows for the formation of a diverse array of imidazole derivatives with moderate to excellent yields.

  通过羟胺和醛的反应原位形成的硝酮与 2-叠氮基丙烯酸酯的反应导致 1,2,4,5-四取代的咪唑的形成。这种三组分反应允许以中等至极好的产率形成多种咪唑衍生物。