(E)-diethyl 2-(5-(4-fluorophenyl)-5-(trifluoromethyl)dihydrofuran-2(3H)-ylidene)succinate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-diethyl 2-(5-(4-fluorophenyl)-5-(trifluoromethyl)dihydrofuran-2(3H)-ylidene)succinate
• 英文别名: diethyl (2E)-2-[5-(4-fluorophenyl)-5-(trifluoromethyl)oxolan-2-ylidene]butanedioate
• 化学式: C₁₉H₂₀F₄O₅
• 分子量: 404.358
• InChiKey: VCUGHJWSDWXQQV-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2,2,2,4'-四氟苯乙酮 、 diethyl 2-(prop-1-en-ylidene)succinate 在 三(4-甲氧苯基)膦 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到(E)-diethyl 2-(5-(4-fluorophenyl)-5-(trifluoromethyl)dihydrofuran-2(3H)-ylidene)succinate
  参考文献：
  名称：

  Phosphine Catalyst-Controlled Cycloaddition or Dienylation Reactions of Trifluoromethyl Aryl Ketones with Bis-Substituted Allenoates

  摘要：

  A chemoselective phosphine-catalyzed cyclo-addition or dienylation reaction between trifluoromethyl-substituted ketones and bis-substituted allenoates was described. Under the catalysis of triarylphosphine, the reaction gave a range of trifluoromethylated tetrahydrofurans with broad substrate tolerance and good to excellent stereo-selectivity, while the use of trialkylphosphine switched the reaction pathway to furnish CF3-substituted dienyl tertiary alcohols, chemoselectivey. Moreover, a preliminary study on the asymmetric version of the reaction was also performed, which represents the first example of a phosphine-catalyzed asymmetric reaction between allenoates and carbonyl compounds.

  DOI：

  10.1021/jo401462c

文献信息

• Phosphine Catalyst-Controlled Cycloaddition or Dienylation Reactions of Trifluoromethyl Aryl Ketones with Bis-Substituted Allenoates
  作者：Hua Xiao、Zhuo Chai、Ri-Sheng Yao、Gang Zhao

  DOI：10.1021/jo401462c

  日期：2013.10.4

  A chemoselective phosphine-catalyzed cyclo-addition or dienylation reaction between trifluoromethyl-substituted ketones and bis-substituted allenoates was described. Under the catalysis of triarylphosphine, the reaction gave a range of trifluoromethylated tetrahydrofurans with broad substrate tolerance and good to excellent stereo-selectivity, while the use of trialkylphosphine switched the reaction pathway to furnish CF3-substituted dienyl tertiary alcohols, chemoselectivey. Moreover, a preliminary study on the asymmetric version of the reaction was also performed, which represents the first example of a phosphine-catalyzed asymmetric reaction between allenoates and carbonyl compounds.