(E,R)-2-hydroxy-4-phenyl-2-trifluoromethyl-but-3-enoic acid ethyl ester | 1623145-68-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E,R)-2-hydroxy-4-phenyl-2-trifluoromethyl-but-3-enoic acid ethyl ester
• 英文别名: (S,E)-ethyl 2-hydroxy-4-phenyl-2-(trifluoromethyl)but-3-enoate
• CAS: 1623145-68-5
• 化学式: C₁₃H₁₃F₃O₃
• 分子量: 274.24
• InChiKey: VZYFTILDHLRSGB-IDVQTMNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 生成 (E,R)-2-hydroxy-4-phenyl-2-trifluoromethyl-but-3-enoic 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

• Lewis Acid Catalyzed Friedel–Crafts Alkylation of Alkenes with Trifluoropyruvates
  作者：Bin Xiang、Teng-Fei Xu、Liang Wu、Ren-Rong Liu、Jian-Rong Gao、Yi-Xia Jia

  DOI：10.1021/acs.joc.6b00358

  日期：2016.5.6

  reaction of styrenes with trifluoropyruvates has been developed, which delivered allylic alcohols in excellent yields (up to 98%) using the Ni(ClO4)2·6H2O/bipyridine complex as a catalyst. The asymmetric reaction was catalyzed by the chiral Cu(OTf)2/bisoxazoline complex to afford the corresponding chiral allylic alcohols bearing trifluoromethylated quaternary stereogenic centers in moderate enantioselectivities

  已开发出苯乙烯与三氟丙酮酸盐的弗瑞德-克来福特烷基化反应，使用Ni（ClO 4）2 ·6H 2 O /联吡啶配合物作为催化剂，可以以极高的收率（高达98％）提供烯丙醇。手性Cu（OTf）2 /双恶唑啉配合物催化不对称反应，得到相应的手性烯丙醇，具有中等对映选择性（最高75％ee）的三氟甲基化季立体中心。