tert-butyl 2-phenyl-5-(trimethylsilyl)-1H-pyrrole-1-carboxylate | 1623145-34-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: tert-butyl 2-phenyl-5-(trimethylsilyl)-1H-pyrrole-1-carboxylate
• CAS: 1623145-34-5
• 化学式: C₁₈H₂₅NO₂Si
• 分子量: 315.488
• InChiKey: DSDUAJZDTFUXJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  31.23
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-phenyl-5-(trimethylsilyl)-1H-pyrrole-1-carboxylate 在 盐酸 、 C₄₄H₃₂P₂Pd⁽²⁺⁾*2F₆Sb^(1-) 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 25.0h， 生成 (R)-tert-butyl 2-(2-ethoxy-1-hydroxy-2-oxoethyl)-5-phenyl-1H-pyrrole-1-carboxylate
  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
• 作为产物：
  描述：

  三甲基氯硅烷 、 N-boc-2-苯基吡咯 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.33h， 以80%的产率得到tert-butyl 2-phenyl-5-(trimethylsilyl)-1H-pyrrole-1-carboxylate
  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