(2R,3R)-4-Carbethoxy-3-(trifluoromethyl)-2-methylbutyroyl chloride | 170079-14-8

• 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-methylbutyroyl chloride
• 英文别名: ethyl (3R,4R)-5-chloro-4-methyl-5-oxo-3-(trifluoromethyl)pentanoate
• CAS: 170079-14-8
• 化学式: C₉H₁₂ClF₃O₃
• 分子量: 260.641
• InChiKey: ORGCVSKKJVZUQN-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 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：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-4-Carbethoxy-3-(trifluoromethyl)-2-methylbutyroyl chloride 、 二甲胺 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以85%的产率得到(3R,4R)-Ethyl N,N-dimethyl-3-(trifluoromethyl)-4-methylglutamate
  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：

  (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

文献信息

• Highly Diastereoselective Michael Addition Reactions of Lithium Enolates to Ethyl 3-Trifluoromethylacrylate
  作者：Takashi Yamazaki、Jiro Haga、Tomoya Kitazume、Shinichiro Nakamura

  DOI：10.1246/cl.1991.2171

  日期：1991.12

  Michael addition reactions of lithium enolates derived from ketones, esters, and amides to ethyl 3-trifluoromethylacrylate were found to proceed smoothly in moderate to excellent chemical yields as well as with a high degree of diastereoselectivity at the newly formed carbon–carbon bond.

  发现来自酮、酯和酰胺的烯醇锂与 3-三氟甲基丙烯酸乙酯的迈克尔加成反应以中等至优异的化学产率顺利进行，并且在新形成的碳-碳键上具有高度的非对映选择性。