2-trifluoromethyl-acrylic-acid 3-nitro-phenyl ester | 1219921-43-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2-trifluoromethyl-acrylic-acid 3-nitro-phenyl ester
• 英文别名: (3-Nitrophenyl) 2-(trifluoromethyl)prop-2-enoate
• CAS: 1219921-43-3
• 化学式: C₁₀H₆F₃NO₄
• 分子量: 261.157
• InChiKey: AKIWNKQOSOTVAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-(三氟甲基)丙烯酸 、 间硝基苯酚 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 以15%的产率得到2-trifluoromethyl-acrylic-acid 3-nitro-phenyl ester
  参考文献：
  名称：

  Preparation of Trifluoromethylated Dihydrocoumarins, Indanones, and Arylpropanoic Acids by Tandem Superacidic Activation of 2-(Trifluoromethyl)acrylic Acid with Arenes

  摘要：

  Indanones and coumarins are important intermediates for the convenient synthesis of many pharmaceutical and biologically active compounds. Fluoroorganics play a vital role in the design of very effective therapeutics due to significant enhancement in their lipophilicity, bioavailability, and fast uptake by the presence of fluorine in these molecules. Herein, we report an efficient one-pot synthesis of trifluoromethylated arylpropanoic acids, indanones, and dihydrocoumarins using Friedel-Crafts alkylation or tandem Friedel-Crafts alkylation-cycloacylation of arenes/phenols with 2-(trifluoromethyl)acrylic acid under superacidic conditions using trifluoromethanesulfonic acid. The results have been rationalized by the structure energy calculations of the involved reaction intermediates using ab initio theoretical methods.

  DOI：

  10.1021/jo9026275

文献信息

• Preparation of Trifluoromethylated Dihydrocoumarins, Indanones, and Arylpropanoic Acids by Tandem Superacidic Activation of 2-(Trifluoromethyl)acrylic Acid with Arenes
  作者：G. K. Surya Prakash、Farzaneh Paknia、Habiba Vaghoo、Golam Rasul、Thomas Mathew、George A. Olah

  DOI：10.1021/jo9026275

  日期：2010.4.2

  Indanones and coumarins are important intermediates for the convenient synthesis of many pharmaceutical and biologically active compounds. Fluoroorganics play a vital role in the design of very effective therapeutics due to significant enhancement in their lipophilicity, bioavailability, and fast uptake by the presence of fluorine in these molecules. Herein, we report an efficient one-pot synthesis of trifluoromethylated arylpropanoic acids, indanones, and dihydrocoumarins using Friedel-Crafts alkylation or tandem Friedel-Crafts alkylation-cycloacylation of arenes/phenols with 2-(trifluoromethyl)acrylic acid under superacidic conditions using trifluoromethanesulfonic acid. The results have been rationalized by the structure energy calculations of the involved reaction intermediates using ab initio theoretical methods.