3,3,3-trifluoro-2-furan-2-yl-2-hydroxy-propionic acid ethyl ester

• 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: 3,3,3-trifluoro-2-furan-2-yl-2-hydroxy-propionic acid ethyl ester
• 英文别名: ethyl (2R)-3,3,3-trifluoro-2-(furan-2-yl)-2-hydroxypropanoate；(R)-ethyl 3,3,3-trifluoro-2-(furan-2-yl)-2-hydroxypropanoate
• 化学式: C₉H₉F₃O₄
• 分子量: 238.163
• InChiKey: UFNDYRHYYNWOCQ-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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：
  59.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  呋喃 、 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 8.0h， 以95%的产率得到3,3,3-trifluoro-2-furan-2-yl-2-hydroxy-propionic acid ethyl ester
  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

• Catalytic, Highly Enantioselective Friedel−Crafts Reactions of Aromatic and Heteroaromatic Compounds to Trifluoropyruvate. A Simple Approach for the Formation of Optically Active Aromatic and Heteroaromatic Hydroxy Trifluoromethyl Esters
  作者：Wei Zhuang、Nicholas Gathergood、Rita G. Hazell、Karl Anker Jørgensen

  DOI：10.1021/jo001176m

  日期：2001.2.1

  in a highly enantioselective aromatic electrophilic reaction and up to 93% ee and good yields are obtained. Furanes and thiophenes give the corresponding 2-hydroxy-trifluoromethyl ethyl esters in high enantiomeric excess; however, the yields of the products are only moderate. Various types of aromatic compounds react in this catalytic reaction with trifluoromethyl pyruvate to give the aromatic electrophilic

  提出了一种新的催化对映选择性合成方法，用于形成光学活性的芳族和杂芳族羟基三氟甲基乙基酯。手性双恶唑啉铜（II）配合物催化三氟丙酮酸丙酮酸酯与芳族和杂芳族化合物的催化对映选择性Friedel-Crafts反应，收率高，对映体过量高。对于一系列取代的吲哚，以高达93％的收率和94％的ee形成相应的3-取代的羟基-三氟甲基乙基酯。吡咯和2-取代的吡咯还在高度对映选择性的芳族亲电子反应中与丙酮酸三氟甲基酯反应，并获得高达93％ee的收率。呋喃和噻吩以高对映体过量得到相应的2-羟基-三氟甲基乙基酯。但是，产品的产量仅中等。在该催化反应中，各种类型的芳族化合物与丙酮酸三氟甲基酯反应，以高收率得到芳族亲电子加成产物。为了获得高的对映体过量（> 80％ee），必须用空间要求的保护基团（例如苄基或烯丙基）保护芳族胺。这防止了胺氮原子与催化剂的配位，因为具有N，N-二甲基基团的芳族胺可能与催化剂配位，导致催化
• 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.
• 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.