(2R,3R)-4-Carbethoxy-3-(trifluoromethyl)-2-methylbutyric acid | 169823-22-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3R)-4-Carbethoxy-3-(trifluoromethyl)-2-methylbutyric acid
• 英文别名: (2R,3R)-5-ethoxy-2-methyl-5-oxo-3-(trifluoromethyl)pentanoic acid
• CAS: 169823-22-7
• 化学式: C₉H₁₃F₃O₄
• 分子量: 242.195
• InChiKey: JBYUWNWEVFSOHV-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-4-Carbethoxy-3-(trifluoromethyl)-2-methylbutyric acid 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 3.5h， 以90%的产率得到(2R,3R)-4-Carbethoxy-3-(trifluoromethyl)-2-methylbutyroyl chloride
  参考文献：
  名称：

  Stereoselective Synthesis of Trifluoromethylated Compounds with Controlled Adjacent Tertiary Carbons by Michael Addition to (E)-3-(Trifluoromethyl)acrylates

  摘要：

  Michael addition reaction of various lithium enolates to ethyl (E)-3-(trifluoromethyl)acrylate (E)-1 was found to be one of the most effective routes to construct materials not only with a CF3 group but also with readily distinguishable multiple functionalities by the routine chemical transformations. Particularly, employment of lithium enolates from chiral acyloxazolidinones as Michael donors resulted in the formation of 1,4-adducts, usually with a high degree of diastereoselectivity as well as with a high degree of diastereofacial selectivities only in a single step. Further, it was suggested by both the experimental results and the ab initio calculations that interaction between fluorine-(s) and lithium strongly stabilized the present Michael intermediates, allowing for the smooth reactions even with ketone enolates under kinetically controlled conditions.

  DOI：

  10.1021/jo00119a013
• 作为产物：
  描述：

  (3R,4R,4'S)-Ethyl 3-(trifluoromethyl)-4-methyl-5-<4'-(1''-methylethyl)-2'-oxazolidinon-3'-yl>-5-oxopentanoate 在 过氧化氢,锂盐(1:1) 作用下， 反应 0.3h， 以96%的产率得到(2R,3R)-4-Carbethoxy-3-(trifluoromethyl)-2-methylbutyric acid
  参考文献：
  名称：

  酰化恶唑烷酮与 3-三氟甲基丙烯酸乙酯的立体选择性迈克尔加成反应

  摘要：

  发现酰基恶唑烷酮与 3-三氟甲基丙烯酸乙酯的迈克尔加成反应在新的碳-碳键处以高度的非对映选择性和非对映选择性顺利进行。

  DOI：

  10.1246/cl.1991.2175