dibenzyl 2-Hexyl-3-oxo-5,7-dihydro-2H-cyclopenta[c]-pyridine-6,6(3H)-dicarboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dibenzyl 2-Hexyl-3-oxo-5,7-dihydro-2H-cyclopenta[c]-pyridine-6,6(3H)-dicarboxylate
• 英文别名: Dibenzyl 2-hexyl-3-oxo-5,7-dihydrocyclopenta[c]pyridine-6,6-dicarboxylate；dibenzyl 2-hexyl-3-oxo-5,7-dihydrocyclopenta[c]pyridine-6,6-dicarboxylate
• 化学式: C₃₀H₃₃NO₅
• 分子量: 487.596
• InChiKey: LMYLHGCLLRUINH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  异氰酸己酯 、 dibenzyl dipropargylmalonate 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以68%的产率得到dibenzyl 2-Hexyl-3-oxo-5,7-dihydro-2H-cyclopenta[c]-pyridine-6,6(3H)-dicarboxylate
  参考文献：
  名称：

  [2+2+2] Cyclotrimerization of Alkynes and Isocyanates/Isothiocyanates Catalyzed by Ruthenium–Alkylidene Complexes

  摘要：

  Ruthenium carbene catalysts are able to catalyze crossed [2+2+2] cyclotrimerizations of alpha,omega-diynes with isocyanates, isothiocyanates, and carbon disulfide. Both aliphatic and aromatic isocyanates can be used to produce fused 2-pyridones, although aliphatic isocyanates were more reactive. Aromatic isocyanates give better results when they bear electron donating substituents. The reaction of unsymmetrical alpha,beta-diynes gave a product only with the substituent adjacent to the 2-pyridone nitrogen. Isothiocyanates gave thiopyranimines upon reaction with the C=S bond, whereas CS2 reacted efficiently to give a thioxothiopyrane.

  DOI：

  10.1021/jo401538p

文献信息

• [2+2+2] Cyclotrimerization of Alkynes and Isocyanates/Isothiocyanates Catalyzed by Ruthenium–Alkylidene Complexes
  作者：Silvia Alvarez、Sandra Medina、Gema Domínguez、Javier Pérez-Castells

  DOI：10.1021/jo401538p

  日期：2013.10.4

  Ruthenium carbene catalysts are able to catalyze crossed [2+2+2] cyclotrimerizations of alpha,omega-diynes with isocyanates, isothiocyanates, and carbon disulfide. Both aliphatic and aromatic isocyanates can be used to produce fused 2-pyridones, although aliphatic isocyanates were more reactive. Aromatic isocyanates give better results when they bear electron donating substituents. The reaction of unsymmetrical alpha,beta-diynes gave a product only with the substituent adjacent to the 2-pyridone nitrogen. Isothiocyanates gave thiopyranimines upon reaction with the C=S bond, whereas CS2 reacted efficiently to give a thioxothiopyrane.