(3R*,4R*)-Ethyl 3-(trifluoromethyl)-4-methyl-5-oxoheptanoate | 138852-11-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: (3R*,4R*)-Ethyl 3-(trifluoromethyl)-4-methyl-5-oxoheptanoate
• 英文别名: ethyl (3S,4S)-4-methyl-5-oxo-3-(trifluoromethyl)heptanoate
• CAS: 138852-11-6；138852-12-7
• 化学式: C₁₁H₁₇F₃O₃
• 分子量: 254.249
• InChiKey: WBUPLHLLWVHRSH-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4,4,4-三氟巴豆酸乙酯 、 3-trimethylsilyloxy-2-pentene 在 甲基锂 作用下， 生成 (3R*,4R*)-Ethyl 3-(trifluoromethyl)-4-methyl-5-oxoheptanoate
  参考文献：
  名称：

  烯醇化锂与 3-三氟甲基丙烯酸乙酯的高度非对映选择性迈克尔加成反应

  摘要：

  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。

  DOI：

  10.1246/cl.1991.2171

文献信息

• Stereoselective Synthesis of Trifluoromethylated Compounds with Controlled Adjacent Tertiary Carbons by Michael Addition to (E)-3-(Trifluoromethyl)acrylates
  作者：Noriyasu Shinohara、Jiro Haga、Takashi Yamazaki、Tomoya Kitazume、Shinichiro Nakamura

  DOI：10.1021/jo00119a013

  日期：1995.7

  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.
• Synthesis of 3,3-dichloro-2-fluoroacrylic esters by thermal opening of alcoxy perhalogeno cyclopropanes
  作者：T. Nguyen、C. Wakselman

  DOI：10.1016/s0022-1139(00)83803-8

  日期：1991.9