2-trifluoromethyl-3-(2',4'-dimethylphenyl)-propanoic acid | 1219921-36-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2-trifluoromethyl-3-(2',4'-dimethylphenyl)-propanoic acid
• 英文别名: 2-[(2,4-Dimethylphenyl)methyl]-3,3,3-trifluoropropanoic acid
• CAS: 1219921-36-4
• 化学式: C₁₂H₁₃F₃O₂
• 分子量: 246.229
• InChiKey: YWNZTROFFJQDDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(三氟甲基)丙烯酸 、 间二甲苯 在 三氟甲磺酸 作用下， 以76%的产率得到2-trifluoromethyl-3-(2',4'-dimethylphenyl)-propanoic acid
  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.