dimethyl 2-(cyclohexylamino)-5-(6'-isopropyl-4'-oxo-4H-chromen-3'-yl)furan-3,4-dicarboxylate | 1214755-64-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: dimethyl 2-(cyclohexylamino)-5-(6'-isopropyl-4'-oxo-4H-chromen-3'-yl)furan-3,4-dicarboxylate
• 英文别名: Dimethyl 2-(cyclohexylamino)-5-(4-oxo-6-propan-2-ylchromen-3-yl)furan-3,4-dicarboxylate
• CAS: 1214755-64-2
• 化学式: C₂₆H₂₉NO₇
• 分子量: 467.519
• InChiKey: QZXLSNALQYYROU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-甲酰基-6-异丙基色酮 、 异氰环已烷 、 丁炔二酸二甲酯 以 苯 为溶剂， 反应 12.0h， 以48%的产率得到dimethyl 2-(cyclohexylamino)-5-(6'-isopropyl-4'-oxo-4H-chromen-3'-yl)furan-3,4-dicarboxylate
  参考文献：
  名称：

  One-Pot Synthesis of Chromenylfurandicarboxylates and Cyclopenta[b]chromenedicarboxylates Involving Zwitterionic Intermediates. A DFT Investigation on the Regioselectivity of the Reaction

  摘要：

  The reaction of 1:1 zwitterionic intermediates generated in situ from either tert-butylisocyanide or cyclohexylisocyanide and acetylenedicarboxylates with 3-formylchromones is described, whereupon either chromenylfurandicarboxylates or cyclopenta[b]chromenedicarboxylates are formed, depending on the nature of the chromone 6-position substituent and also on the acetylene ester group. In addition, from the reaction with a 1:2 zwitterionic intermediate, cyclohepta[b]chromenetetra-carboxylates are isolated. The regioselectivity of the reaction was also investigated by DFT calculations. The geometries of the reactants, intermediate zwitterions, transition structures, and intermediate products, leading to the final products, were optimized using the B3LYP functional with the 6-31G(d) basis set. The structures of the products were elucidated by 1D and 2D NMR experiments. Full assignment of all H-1 and C-13 NMR chemical shifts has been achieved. Plausible mechanistic schemes are provided.

  DOI：

  10.1021/jo902702j

文献信息

• One-Pot Synthesis of Chromenylfurandicarboxylates and Cyclopenta[<i>b</i>]chromenedicarboxylates Involving Zwitterionic Intermediates. A DFT Investigation on the Regioselectivity of the Reaction
  作者：Michael A. Terzidis、Julia Stephanidou-Stephanatou、Constantinos A. Tsoleridis

  DOI：10.1021/jo902702j

  日期：2010.3.19

  The reaction of 1:1 zwitterionic intermediates generated in situ from either tert-butylisocyanide or cyclohexylisocyanide and acetylenedicarboxylates with 3-formylchromones is described, whereupon either chromenylfurandicarboxylates or cyclopenta[b]chromenedicarboxylates are formed, depending on the nature of the chromone 6-position substituent and also on the acetylene ester group. In addition, from the reaction with a 1:2 zwitterionic intermediate, cyclohepta[b]chromenetetra-carboxylates are isolated. The regioselectivity of the reaction was also investigated by DFT calculations. The geometries of the reactants, intermediate zwitterions, transition structures, and intermediate products, leading to the final products, were optimized using the B3LYP functional with the 6-31G(d) basis set. The structures of the products were elucidated by 1D and 2D NMR experiments. Full assignment of all H-1 and C-13 NMR chemical shifts has been achieved. Plausible mechanistic schemes are provided.