ethyl (Z)-2-azido-3-(4-fluorophenyl)acrylate

• 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: ethyl (Z)-2-azido-3-(4-fluorophenyl)acrylate
• 英文别名: ethyl (Z)-2-azido-3-(4-fluorophenyl)prop-2-enoate
• 化学式: C₁₁H₁₀FN₃O₂
• 分子量: 235.218
• InChiKey: AOYNGQZZXARODP-YFHOEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (Z)-2-azido-3-(4-fluorophenyl)acrylate 在 喹啉 、 铜 、 溶剂黄146 、 sodium hydroxide 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 乙醇 为溶剂， 反应 26.0h， 生成 1-(6-氟-1H-吲哚-3-基)-乙酮
  参考文献：
  名称：

  Synthesis and anti-tumor activity of 2-amino-3-cyano-6-(1H-indol-3-yl)-4-phenylpyridine derivatives in vitro

  摘要：

  A series of novel 2-amino-3-cyano-6-(1H-indol-3-yl)-4-phenylpyridine derivatives were synthesized and their cytotoxic activity against A549, H460, HT-29 and SMMC-7721 cell lines was evaluated in vitro. Among them, ten compounds (10, 11, 14, 16, 17, 26, 27, 29, 30 and 31) displayed excellent anti-tumor activity against different cell lines. The most promising compound 27 showed strong anti-tumor activity against A549, H460, HT-29 and SMMC-7721 cell lines with IC50 values of 22, 0.23, 0.65 and 0.77 nM, which were 2.6-, 83-, 1.1 x 10(3)- and 2.0 x 10(3)- fold more active than MX-58151 (IC50 values of 0.058, 0.019, 0.70 and 1.53 mu M), respectively. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.055
• 作为产物：
  描述：

  叠氮乙酸乙酯 、 对氟苯甲醛 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以64%的产率得到ethyl (Z)-2-azido-3-(4-fluorophenyl)acrylate
  参考文献：
  名称：

  利用光级联工艺从乙烯基叠氮化物可见光介导合成吡嗪

  摘要：

  已开发出一种从乙烯基叠氮化物合成取代吡嗪的简便方法。这种方法是通过可见光光催化的双能和电子转移策略实现的。最初，乙烯基叠氮化物在水的存在下通过激发的钌光催化剂的三重敏化过程活化以形成二氢吡嗪，然后在氧气（空气）气氛下进行单电子转移（SET）过程，导致四取代的吡嗪在良好的产量。

  DOI：

  10.1055/s-0036-1590888

文献信息

• Visible-Light-Mediated Synthesis of Pyrazines from Vinyl Azides Utilizing a Photocascade Process
  作者：Asik Hossain、Santosh Pagire、Oliver Reiser

  DOI：10.1055/s-0036-1590888

  日期：2017.9

  A convenient method for the synthesis of substituted pyrazines from vinyl azides has been developed. This method is enabled by a dual-energy and electron-transfer strategy by visible-light photocatalysis. Initially, vinyl azides are activated by a triplet sensitization process from an excited ruthenium photocatalyst in the presence of water to form dihydropyrazines, followed by a single-electron-transfer

  已开发出一种从乙烯基叠氮化物合成取代吡嗪的简便方法。这种方法是通过可见光光催化的双能和电子转移策略实现的。最初，乙烯基叠氮化物在水的存在下通过激发的钌光催化剂的三重敏化过程活化以形成二氢吡嗪，然后在氧气（空气）气氛下进行单电子转移（SET）过程，导致四取代的吡嗪在良好的产量。
• A Tandem Approach to Isoquinolines from 2-Azido-3-arylacrylates and α-Diazocarbonyl Compounds
  作者：Yun-Yun Yang、Wang-Ge Shou、Zheng-Bo Chen、Deng Hong、Yan-Guang Wang

  DOI：10.1021/jo8003259

  日期：2008.5.1

  2-Azido-3-arylacrylates react with α-diazocarbonyl compounds and triphenylphosphine to furnish isoquinolines in 60−92% yields. The tandem process involves a Wolff rearrangement, an aza-Wittig reaction, and an electrocyclic ring closure. The procedure is efficient, rapid, and general, and the substrates are readily available.

  2-氮杂-3-芳基丙烯酸酯与α-重氮羰基化合物和三苯膦反应生成异喹啉，收率60-92％。串联过程涉及Wolff重排，aza-Wittig反应和电环闭合。该过程是有效，快速和通用的，并且基材是容易获得的。
• Synthesis of 5-arylidene-3-(pyridin-4-yl)-2-thio-imidazolidinone derivatives with the end of flexible chain modified with aryl groups under microwave
  作者：Chongyang Mao、Zhen Cao、Boqiao Fu、Shengcheng Wang、Haowei Chen、Caifen Xia、Xinliang Hu、Xinyuan Huang、Caiqin Qin

  DOI：10.1080/00397911.2022.2047727

  日期：2022.3.4
• Synthesis and anti-tumor activity of 2-amino-3-cyano-6-(1H-indol-3-yl)-4-phenylpyridine derivatives in vitro
  作者：Fan Zhang、Yanfang Zhao、Li Sun、Lu Ding、Yucheng Gu、Ping Gong

  DOI：10.1016/j.ejmech.2011.03.055

  日期：2011.7

  A series of novel 2-amino-3-cyano-6-(1H-indol-3-yl)-4-phenylpyridine derivatives were synthesized and their cytotoxic activity against A549, H460, HT-29 and SMMC-7721 cell lines was evaluated in vitro. Among them, ten compounds (10, 11, 14, 16, 17, 26, 27, 29, 30 and 31) displayed excellent anti-tumor activity against different cell lines. The most promising compound 27 showed strong anti-tumor activity against A549, H460, HT-29 and SMMC-7721 cell lines with IC50 values of 22, 0.23, 0.65 and 0.77 nM, which were 2.6-, 83-, 1.1 x 10(3)- and 2.0 x 10(3)- fold more active than MX-58151 (IC50 values of 0.058, 0.019, 0.70 and 1.53 mu M), respectively. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Design, synthesis, antiviral and fungicidal activities of novel polycarpine simplified analogues
  作者：Lili Yan、Yongyue Gao、Taiqing Li、Xiangyu Wang、Rong Xie、Yaxi Liu、Yuxuan Xie、Ziwen Wang、Aidang Lu、Qingmin Wang

  DOI：10.1016/j.bioorg.2023.106508

  日期：2023.6

  and antiviral agents have been used to treat plant diseases caused by plant pathogenic fungi and viruses, but their use has been criticized due to their adverse side effects. As alternative strategies, natural fungicides and antiviral agents have attracted many researchers’ interest in recent years. Herein, we designed and synthesized a series of novel polycarpine simplified analogues. Antiviral activity

  真菌和病毒性疾病占微生物病害造成的农业生产损失的 70-80%。合成杀菌剂和抗病毒剂已被用于治疗由植物病原真菌和病毒引起的植物病害，但由于其不良副作用，它们的使用一直受到批评。作为替代策略，天然杀菌剂和抗病毒剂近年来引起了许多研究人员的兴趣。在此，我们设计并合成了一系列新颖的聚芸香碱简化类似物。针对烟草花叶病毒（TMV）的抗病毒活性研究表明，大多数设计的化合物都具有良好的抗病毒活性。4 , 6d , 6f , 6h , 和8c的杀病毒活性高于聚芸香碱，与宁南霉素相似。选择结构简化的化合物8c进行进一步的抗病毒机制研究，结果表明化合物8c可通过作用于TMV外壳蛋白抑制20S蛋白圆盘的形成。这些化合物还对 7 种植物真菌表现出广谱杀菌活性。该工作为聚芸香碱简化类似物在作物保护中的应用奠定了基础。