2-(tert-butyl) 1,1-diethyl 2-(1-phenyl-1H-pyrrol-3-yl)ethane-1,1,2-tricarboxylate | 1177009-61-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-(tert-butyl) 1,1-diethyl 2-(1-phenyl-1H-pyrrol-3-yl)ethane-1,1,2-tricarboxylate
• CAS: 1177009-61-8
• 化学式: C₂₃H₂₉NO₆
• 分子量: 415.486
• InChiKey: KPEJFUUFIKWPEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  83.83
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  1-苯基吡咯 、 1,1-diethyl 2-tert-butyl ethenetricarboxylate 在 copper(II) bis(trifluoromethanesulfonate) 、 (4R,4’R)-2,2’-(propane-2,2-diyl)bis(4-benzyl-4,5-dihydrooxazole) 作用下， 以 四氢呋喃 为溶剂， 生成 2-(tert-butyl) 1,1-diethyl 2-(1-phenyl-1H-pyrrol-3-yl)ethane-1,1,2-tricarboxylate 、 2-O-tert-butyl 1-O,1-O-diethyl (2R)-2-(1-phenylpyrrol-2-yl)ethane-1,1,2-tricarboxylate 、 2-O-tert-butyl 1-O,1-O-diethyl (2R)-2-(1-phenylpyrrol-2-yl)ethane-1,1,2-tricarboxylate
  参考文献：
  名称：

  Enantioselective Friedel–Crafts reactions of ethenetricarboxylates and substituted pyrroles and furans and intramolecular reaction of benzene derivatives

  摘要：

  Compared to enantioselective Friedel-Crafts reactions of indoles, reactions of alkylidene malonates with monocyclic aromatic compounds generally proceed with low enantioselectivity. The Friedel-Crafts reactions of ethenetricarboxylates 1 and monocyclic heteroaromatic compounds, such as substituted pyrroles and furans were investigated. The reaction of 1 with 2,4-dimethylpyrrole in the presence of a chiral bis-oxazoline-copper(II) complex (10 mol %) in tetrahydrofuran at room temperature gave alkylated products in up to 72% ee. The reaction of 1 with 2-substituted furans gave alkylated products in 46-62% ee. The absolute stereochemistry of the furan Friedel-Crafts product 7e was determined by transformation to the known 2,3-dimethylbutyric acid. The intramolecular reaction of benzene derivatives gave cyclized products up to 56% ee. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.05.016