(R)-methyl 2-hydroxy-4-phenyl-2-(trifluoromethyl)pent-4-enoate

• 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: (R)-methyl 2-hydroxy-4-phenyl-2-(trifluoromethyl)pent-4-enoate
• 英文别名: methyl (2R)-2-hydroxy-4-phenyl-2-(trifluoromethyl)pent-4-enoate
• 化学式: C₁₃H₁₃F₃O₃
• 分子量: 274.24
• InChiKey: XKZYGCRJYHAUOT-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  三氟丙酮酸甲酯 、 2-苯基-1-丙烯 在 2,6-双[(3aR,8aS)-(+)-8H-茚[1,2-d]恶唑啉-2-基]吡啶 、 indium(III) chloride 、 silver hexafluoroantimonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以99%的产率得到(R)-methyl 2-hydroxy-4-phenyl-2-(trifluoromethyl)pent-4-enoate
  参考文献：
  名称：

  Highly Enantioselective Ketone-Ene Reactions of Trifluoropyruvate: Significant Counterion Effect of the In(III)−PyBox Complex

  摘要：

  A chiral indium(III)-pybox complex catalyzed asymmetric ketone-ene reaction of trifluoropyruvate is described. Both aromatic and aliphatic 1,1-disubstituted alkenes reacted smoothly to give the enantioenriched tertiary homoallylic alcohols in good to excellent yields (up to 99%) and with excellent enantioselectivities (up to 98% ee).

  DOI：

  10.1021/ol902507x

文献信息

• Chiral Bis(imidazolinyl)phenyl NCN Pincer Rhodium(III) Catalysts for Enantioselective Allylation of Aldehydes and Carbonyl–Ene Reaction of Trifluoropyruvates
  作者：Tao Wang、Xin-Qi Hao、Juan-Juan Huang、Jun-Long Niu、Jun-Fang Gong、Mao-Ping Song

  DOI：10.1021/jo4014194

  日期：2013.9.6

  Chiral NCN pincer rhodium(III) complexes with bis(imidazolinyl)phenyl ligands were found to be effective catalysts for the allylation of a variety of electronically and structurally diverse aldehydes with allyltributyltin, giving the corresponding optically active homoallylic alcohols in high yields with enantioselectivities of up to 97% ee. These complexes were also applied in the carbonyl–ene reaction

  发现具有双（咪唑啉基）苯基配体的手性NCN钳形铑（III）配合物是有效的催化剂，用于将各种电子和结构不同的醛与烯丙基三丁基锡进行烯丙基化，从而以高收率得到相应的光学活性均烯醇，且对映选择性高达到97％ee。这些配合物还用于三氟丙酮酸乙酯或三氟丙酮酸甲酯与各种2-芳基丙烯的羰基-烯反应中。借助三氟甲磺酸银，钳型铑（III）催化剂可以催化反应，以高收率和高立体选择性（最高95％ee）提供相应的手性α-羟基-α-三氟甲基酯。
• Enantioselective Carbonyl‐Ene Reactions of Trifluoropyruvate in Ionic Liquid <i>via</i> a Recyclable Indium(III)‐Pybox Complex
  作者：Jun Feng Zhao、Boon Hong Tan、Ming Kui Zhu、Teguh Budiono W. Tjan、Teck Peng Loh

  DOI：10.1002/adsc.201000170

  日期：2010.10.9

  A highly enantioselective carbonyl-ene reaction of trifluoropyruvate catalyzed by a recyclable indium(III)-pybox complex in ionic liquid afforded trifluoromethyl-containing tertiary homoallylic alcohols with excellent yields (up to 98%) and enantioselectivities (up to 98% ee). Notably, this catalytic system can be recycled up to seven cycles.

  在离子液体中由可回收的铟（III）-pybox络合物催化的三氟丙酮酸的高对映选择性羰基-烯反应提供了具有优异收率（高达98％）和对映选择性（高达98％ee）的含三氟甲基的叔均烯丙基醇。值得注意的是，该催化系统最多可循环使用七个周期。
• Highly Enantioselective Organocatalytic Carbonyl-Ene Reaction with Strongly Acidic, Chiral Brønsted Acids as Efficient Catalysts
  作者：Magnus Rueping、Thomas Theissmann、Alexander Kuenkel、René M. Koenigs

  DOI：10.1002/anie.200802139

  日期：2008.8.25
• Highly Enantioselective Ketone-Ene Reactions of Trifluoropyruvate: Significant Counterion Effect of the In(III)−PyBox Complex
  作者：Jun-Feng Zhao、Teguh-Budiono W. Tjan、Boon-Hong Tan、Teck-Peng Loh

  DOI：10.1021/ol902507x

  日期：2009.12.17

  A chiral indium(III)-pybox complex catalyzed asymmetric ketone-ene reaction of trifluoropyruvate is described. Both aromatic and aliphatic 1,1-disubstituted alkenes reacted smoothly to give the enantioenriched tertiary homoallylic alcohols in good to excellent yields (up to 99%) and with excellent enantioselectivities (up to 98% ee).