(R)-ethyl 2-(4,5-diphenylfuran-2-yl)-2-hydroxyacetate | 1623145-81-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: (R)-ethyl 2-(4,5-diphenylfuran-2-yl)-2-hydroxyacetate
• 英文别名: ethyl (2R)-2-(4,5-diphenylfuran-2-yl)-2-hydroxyacetate
• CAS: 1623145-81-2
• 化学式: C₂₀H₁₈O₄
• 分子量: 322.361
• InChiKey: MDLHUIBGXIFVPJ-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,2-diphenyl-4-(trimethylsilyl)but-3-yne-1,2-diol 在 盐酸 、 C₄₄H₃₂P₂Pd⁽²⁺⁾*2F₆Sb^(1-) 、 C₁₈H₂₈AuCl₂P₂ 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 28.0h， 生成 (R)-ethyl 2-(4,5-diphenylfuran-2-yl)-2-hydroxyacetate
  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 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.