ethyl (2R)-2-(5-allylthiophen-2-yl)-3,3,3-trifluoro-2-hydroxypropanoate | 1373133-14-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: ethyl (2R)-2-(5-allylthiophen-2-yl)-3,3,3-trifluoro-2-hydroxypropanoate
• 英文别名: ethyl (2R)-3,3,3-trifluoro-2-hydroxy-2-(5-prop-2-enylthiophen-2-yl)propanoate
• CAS: 1373133-14-2
• 化学式: C₁₂H₁₃F₃O₃S
• 分子量: 294.295
• InChiKey: NNMORZAXNASVAT-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-allylthiophene 、 3,3,3-三氟丙酮酸乙酯 在 R(+)-o'-(1,1'-binaphthyl-2,2'-diyl)bis(diphenylphosphane)palladium(II) bis(triflate) 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 ethyl (2R)-2-(5-allylthiophen-2-yl)-3,3,3-trifluoro-2-hydroxypropanoate 、 ethyl (2R)-2-(5-allylthiophen-2-yl)-3,3,3-trifluoro-2-hydroxypropanoate
  参考文献：
  名称：

  Asymmetric carbonyl-ene and Friedel–Crafts reactions catalysed by Lewis acid platinum group metal complexes of the enantiopure atropisomeric biaryl-like diphosphine (S)-Me2-CATPHOS: a comparison with BINAP

  摘要：

  Lewis acid platinum and palladium complexes of (S)-Me-2-CATPHOS catalyse the carbonyl-ene reaction between allylbenzene derivatives and ethyl trifluoropyruvate to give the expected alpha-hydroxy esters with ee's up to 97%, while the corresponding reaction involving 2-allylfuran and thiophene was exclusively selective for Friedel-Crafts-type reactivity and gave the corresponding 2-hydroxy-trifluoromethyl ethyl esters in good yield and moderate to good enantioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.01.022

文献信息

• Asymmetric carbonyl-ene and Friedel–Crafts reactions catalysed by Lewis acid platinum group metal complexes of the enantiopure atropisomeric biaryl-like diphosphine (S)-Me2-CATPHOS: a comparison with BINAP
  作者：Simon Doherty、Julian G. Knight、Hamid Mehdi-Zodeh

  DOI：10.1016/j.tetasy.2012.01.022

  日期：2012.2

  Lewis acid platinum and palladium complexes of (S)-Me-2-CATPHOS catalyse the carbonyl-ene reaction between allylbenzene derivatives and ethyl trifluoropyruvate to give the expected alpha-hydroxy esters with ee's up to 97%, while the corresponding reaction involving 2-allylfuran and thiophene was exclusively selective for Friedel-Crafts-type reactivity and gave the corresponding 2-hydroxy-trifluoromethyl ethyl esters in good yield and moderate to good enantioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.