2-(4-fluorophenyl)-4-vinyl-2,5-dihydrofuran-3-carboxylic acid | 1309359-51-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-fluorophenyl)-4-vinyl-2,5-dihydrofuran-3-carboxylic acid
• 英文别名: 4-Ethenyl-2-(4-fluorophenyl)-2,5-dihydrofuran-3-carboxylic acid
• CAS: 1309359-51-0
• 化学式: C₁₃H₁₁FO₃
• 分子量: 234.227
• InChiKey: NWKUHVVHERVMDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-fluorophenyl)-4-vinyl-2,5-dihydrofuran-3-carboxylic acid 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 N-(4-ethoxyphenyl)-2-(4-fluorophenyl)-4-vinyl-2,5-dihydrofuran-3-carboxamide
  参考文献：
  名称：

  Synthesis of novel 2, 5-dihydrofuran derivatives and evaluation of their anticancer activity

  摘要：

  According to metal-catalyzed [3 + 2] cycloaddition reaction, we synthesized a series of novel 2, 5-dihydrofuran derivatives and evaluated their in vitro anti-cancer activities via MTT method. The bioassay showed that the majority of the resultant compounds exerted anti-tumor effect against four human cancer cell lines to various extents, which supported the rationale of the design. Compounds 9e and 10g showed the highest activity with broad anti-cancer spectrum, which were good candidates for further evaluation. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.11.036
• 作为产物：
  描述：

  对氟苯甲醛 在 哌啶 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲苯 、 mineral oil 为溶剂， 反应 21.08h， 生成 2-(4-fluorophenyl)-4-vinyl-2,5-dihydrofuran-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of novel 2, 5-dihydrofuran derivatives and evaluation of their anticancer activity

  摘要：

  According to metal-catalyzed [3 + 2] cycloaddition reaction, we synthesized a series of novel 2, 5-dihydrofuran derivatives and evaluated their in vitro anti-cancer activities via MTT method. The bioassay showed that the majority of the resultant compounds exerted anti-tumor effect against four human cancer cell lines to various extents, which supported the rationale of the design. Compounds 9e and 10g showed the highest activity with broad anti-cancer spectrum, which were good candidates for further evaluation. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.11.036

文献信息

• Efficient and mild synthesis of highly substituted 2,5-dihydrofuran and furan derivatives via stepwise reaction
  作者：Tiantian Wang、Jia Liu、Zhiliang Lv、Hanyu Zhong、Huan Chen、Chunjuan Niu、Ke Li

  DOI：10.1016/j.tet.2011.03.038

  日期：2011.5

  An efficient and mild synthesis of highly substituted 2,5-dihydrofuran and furan derivatives from a variety of alkylidene malonates and 1,4-butyne-diol via one-pot reaction was applied. With various conditions of base amount, temperature and time applied to the reaction, the 2,5-dihydrofuran and the furan derivatives could be selectively obtained. Moreover, the formation of furan derivatives with 2

  通过一锅反应，从各种亚烷基丙二酸酯和1,4-丁炔二醇高效，温和地合成了高度取代的2,5-二氢呋喃和呋喃衍生物。通过将碱量，温度和时间应用于反应的各种条件，可以选择性地获得2，5-二氢呋喃和呋喃衍生物。此外，还研究了以2，5-二氢呋喃衍生物为中间体的呋喃衍生物的形成。这些2，5-二氢呋喃衍生物中的一些对HeLa细胞显示出有效的体外抗肿瘤活性。