ethyl (Z)-1,1,1-trifluoro-2-propyloxyoxobutenoate | 152188-55-1

• 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: ethyl (Z)-1,1,1-trifluoro-2-propyloxyoxobutenoate
• 英文别名: ethyl 4,4,4-trifluoro-3-propyloxy-2-butenoate；ethyl (Z)-4,4,4-trifluoro-3-propoxybut-2-enoate
• CAS: 152188-55-1
• 化学式: C₉H₁₃F₃O₃
• 分子量: 226.196
• InChiKey: GHOTZQZUPGJFQF-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl (Z)-1,1,1-trifluoro-2-propyloxyoxobutenoate 、 N-(trimethylsilylmethyl)-N-(pentoxymethyl)-benzylamine 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以30%的产率得到(3S,4S)-1-Benzyl-4-propoxy-4-trifluoromethyl-pyrrolidine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Enhancement of alkene reactivity by a trifluoromethyl group: Synthesis of pyrrolidines via 1,3-dipolar cycloaddition

  摘要：

  Ethylenic compounds activated by a trifluoromethyl group undergo 1,3-dipolar cycloadditions with non-stabilized azomethine ylides to provide polysubstituted 3-trifluoromethyl-pyrrolidines in good yields, while non-fluorinated parent alkenes are in most cases unreactive in these reactions.

  DOI：

  10.1016/s0040-4039(00)73681-1
• 作为产物：
  描述：

  三氟乙酰乙酸乙酯 、 1-碘代丙烷 生成 ethyl (Z)-1,1,1-trifluoro-2-propyloxyoxobutenoate
  参考文献：
  名称：

  AUBERT, CORINNE;BEGUE, JEAN-PIERRE;CHARPENTIER-MORIZE, MICHELINE;NEE, GER+, J. FLUOR. CHEM., 44,(1989) N, C. 361-376

  摘要：

  DOI：

文献信息

• Alkylation of ethyl 4,4,4-trifluoroacetoacetate. First example of a reversible O-alkylation process leading to C-alkylation
  作者：Jean-Pierre Bégué、Micheline Charpentier-Morize、Gérard Née

  DOI：10.1039/c39890000083

  日期：——

  polar solvents the ratio of O vs. C alkylation products of ethyl 4,4,4-trifluoroacetoacetate (ETFAA)can be dependent on reaction time; in hexamethylphosphoric triamide (HMPA) or acetone, the SN2 cleavage of enol ethers of ETFAA with sodium iodide was observed with concomitant formation of the sodium enolate and the corresponding iodides, and in the case of an activated iodide the mono- and di-alkylation

  在非质子极性溶剂中，4,4,4-三氟乙酰乙酸乙酯（ETFAA）的O与C烷基化产物之比取决于反应时间。在六甲基磷酸三酰胺（HMPA）或丙酮中，观察到ETFAA的烯醇醚与碘化钠的S N 2裂解，同时形成了烯醇酸钠和相应的碘化物，在活化碘化物的情况下，单和二碘化物定量得到烷基化产物。
• Trifluoromethylalkenes in cycloaddition reactions
  作者：Danièle Bonnet-Delpon、Jean-Pierre Bégué、Thierry Lequeux、Michèle Ourevitch

  DOI：10.1016/0040-4020(95)00885-c

  日期：1996.1

  CF3-Substituted alkenes have been described to be good partners in Diels-Alder reactions with the Danishefsky's diene and in 1,3-dipolar cycloadditions with nitrones and non-stabilized azomethine ylides. The influence of the CF3-group on both the activation of the double bond and the stereochemistry of the cycloaddition has been evaluated. New CF3-substituted mono- and polycyclic compounds 4 and 7, highly functionalized isoxazolidines 18, 19, 22 and 23 and pyrrolidines 12, 13 and 16 have been prepared.
• BEGUE, JEAN-PIERRE;CHARPENTIER-MORIZE, MICHELINE;NEE, GERARD, J. CHEM. SOC. CHEM. COMMUN.,(1989) N, C. 83-84
  作者：BEGUE, JEAN-PIERRE、CHARPENTIER-MORIZE, MICHELINE、NEE, GERARD

  DOI：——

  日期：——
• AUBERT, CORINNE;BEGUE, JEAN-PIERRE;CHARPENTIER-MORIZE, MICHELINE;NEE, GER+, J. FLUOR. CHEM., 44,(1989) N, C. 361-376
  作者：AUBERT, CORINNE、BEGUE, JEAN-PIERRE、CHARPENTIER-MORIZE, MICHELINE、NEE, GER+

  DOI：——

  日期：——
• Enhancement of alkene reactivity by a trifluoromethyl group: Synthesis of pyrrolidines via 1,3-dipolar cycloaddition
  作者：Jean-Pierre Bégué、Danièle Bonnet-Delpon aThierry Lequeux

  DOI：10.1016/s0040-4039(00)73681-1

  日期：1993.5

  Ethylenic compounds activated by a trifluoromethyl group undergo 1,3-dipolar cycloadditions with non-stabilized azomethine ylides to provide polysubstituted 3-trifluoromethyl-pyrrolidines in good yields, while non-fluorinated parent alkenes are in most cases unreactive in these reactions.