(R)-ethyl 3,3,3-trifluoro-2-hydroxy-2-(thiophen-2-yl)propanoate | 1020747-93-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (R)-ethyl 3,3,3-trifluoro-2-hydroxy-2-(thiophen-2-yl)propanoate
• 英文别名: ethyl (2R)-3,3,3-trifluoro-2-hydroxy-2-(thiophen-2-yl)propanoate；(2R)-ethyl 3,3,3-trifluoro-2-hydroxy-2-(2-thienyl)propanoate；Ethyl (I+/-R)-I+/--hydroxy-I+/--(trifluoromethyl)-2-thiopheneacetate；ethyl (2R)-3,3,3-trifluoro-2-hydroxy-2-thiophen-2-ylpropanoate
• CAS: 1020747-93-6
• 化学式: C₉H₉F₃O₃S
• 分子量: 254.23
• InChiKey: IRUXGAPHRKSSMF-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  噻吩 、 3,3,3-三氟丙酮酸乙酯 在 C₄₄H₃₂P₂Pd⁽²⁺⁾*2F₆Sb^(1-) 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 24.0h， 以89%的产率得到(R)-ethyl 3,3,3-trifluoro-2-hydroxy-2-(thiophen-2-yl)propanoate
  参考文献：
  名称：

  Catalytic and highly enantioselective Friedel–Crafts type reactions of heteroaromatic compounds with trifluoropyruvate and glyoxylate by a dicationic palladium complex

  摘要：

  The highly enantioselective Friedel-Crafts alkylation of furan and thiophene derivatives with trifluoropyruvate, which have never provided the high level of asymmetric induction and yield until now, was achieved by using dicationic palladium complexes as Lewis acid catalysts. Moreover, glyoxylate instead of trifluoropyruvate as an electrophile led to complete change of regioselectivity with 2-trimethylsilylated furan, thiophene, and pyrrole derivatives to give the corresponding heteroarylated products in high yields and enantioselectivities. The respective products with trifluoropyruvate and glyoxylate could also be obtained via sequential catalytic reaction; intramolecular cyclization of alkynyldiols using cationic Au catalyst followed by Friedel-Crafts type reactions using dicationic Pd catalyst. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.06.013

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.
• WO2007/38444
  申请人：——

  公开号：——

  公开（公告）日：——
• WO2008/48540
  申请人：——

  公开号：——

  公开（公告）日：——
• Catalytic and highly enantioselective Friedel–Crafts type reactions of heteroaromatic compounds with trifluoropyruvate and glyoxylate by a dicationic palladium complex
  作者：Kohsuke Aikawa、Yuya Asai、Yūta Hioki、Koichi Mikami

  DOI：10.1016/j.tetasy.2014.06.013

  日期：2014.8

  The highly enantioselective Friedel-Crafts alkylation of furan and thiophene derivatives with trifluoropyruvate, which have never provided the high level of asymmetric induction and yield until now, was achieved by using dicationic palladium complexes as Lewis acid catalysts. Moreover, glyoxylate instead of trifluoropyruvate as an electrophile led to complete change of regioselectivity with 2-trimethylsilylated furan, thiophene, and pyrrole derivatives to give the corresponding heteroarylated products in high yields and enantioselectivities. The respective products with trifluoropyruvate and glyoxylate could also be obtained via sequential catalytic reaction; intramolecular cyclization of alkynyldiols using cationic Au catalyst followed by Friedel-Crafts type reactions using dicationic Pd catalyst. (C) 2014 Elsevier Ltd. All rights reserved.