(E)-1-ethyl 6-methyl 2-cyano-5-hydroxy-4,4-dimethyl-5-(trifluoromethyl)hex-2-enedioate | 1099074-45-9

• 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: (E)-1-ethyl 6-methyl 2-cyano-5-hydroxy-4,4-dimethyl-5-(trifluoromethyl)hex-2-enedioate
• 英文别名: 1-O-ethyl 6-O-methyl (E)-2-cyano-5-hydroxy-4,4-dimethyl-5-(trifluoromethyl)hex-2-enedioate
• CAS: 1099074-45-9
• 化学式: C₁₃H₁₆F₃NO₅
• 分子量: 323.269
• InChiKey: JGDASZGSFWXJSN-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  96.6
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  三氟丙酮酸甲酯 、 ethyl (E)-2-cyano-4-methylpent-2-enoate 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以78%的产率得到(E)-1-ethyl 6-methyl 2-cyano-5-hydroxy-4,4-dimethyl-5-(trifluoromethyl)hex-2-enedioate
  参考文献：
  名称：

  Organic base catalyzed carbonyl allylation of methyl trifluoropyruvate with activated alkenes

  摘要：

  The carbonyl allylation of methyl trifluoropyruvate (MeTFP) with activated alkenes has been investigated in detail using organic bases as catalysts. Organic bases, such as DMAP, Et3N, DABCO, NMM, Et2NH, and quinine, could deprotonate the allylic hydrogen of activated alkenes and furnish nucleophilic species to undergo the addition reaction with methyl trifluoropyruvate and afford versatile homoallylic alcohols with CF3 group in excellent yields. The F-19 NMR monitoring indicated that the isomerization induced by base gave two separable diastereoisomers in an equilibrium ratio of 1:3. The relative configuration of hydroxy and the neighboring alkyl group in the major diastereoisomer was determined as syn-configuration by X-ray diffraction analysis. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.002

文献信息

• Organic base catalyzed carbonyl allylation of methyl trifluoropyruvate with activated alkenes
  作者：Fan Zhang、Xiao-Jin Wang、Chen-Xin Cai、Jin-Tao Liu

  DOI：10.1016/j.tet.2008.11.002

  日期：2009.1

  The carbonyl allylation of methyl trifluoropyruvate (MeTFP) with activated alkenes has been investigated in detail using organic bases as catalysts. Organic bases, such as DMAP, Et3N, DABCO, NMM, Et2NH, and quinine, could deprotonate the allylic hydrogen of activated alkenes and furnish nucleophilic species to undergo the addition reaction with methyl trifluoropyruvate and afford versatile homoallylic alcohols with CF3 group in excellent yields. The F-19 NMR monitoring indicated that the isomerization induced by base gave two separable diastereoisomers in an equilibrium ratio of 1:3. The relative configuration of hydroxy and the neighboring alkyl group in the major diastereoisomer was determined as syn-configuration by X-ray diffraction analysis. (C) 2008 Elsevier Ltd. All rights reserved.