Tetraethyl 6,12-bis(2,4,5-trimethoxyphenyl)-3,9-diazapentacyclo[6.4.0.02,7.04,11.05,10]dodecane-1,5,7,11-tetracarboxylate | 1231763-87-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Tetraethyl 6,12-bis(2,4,5-trimethoxyphenyl)-3,9-diazapentacyclo[6.4.0.02,7.04,11.05,10]dodecane-1,5,7,11-tetracarboxylate
• 英文别名: tetraethyl 6,12-bis(2,4,5-trimethoxyphenyl)-3,9-diazapentacyclo[6.4.0.02,7.04,11.05,10]dodecane-1,5,7,11-tetracarboxylate
• CAS: 1231763-87-3
• 化学式: C₄₀H₅₀N₂O₁₄
• 分子量: 782.842
• InChiKey: YEEVTKRRGKMTIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  56
• 可旋转键数：
  20
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  185
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  diethyl 4-(2,4,5-trimethoxylphenyl)-1,4-dihydropyridine-3,5-dicarboxylate 在 1-methyl-3-(2-(naphthalen-2-yl)-2-oxoethyl)-1H-imidazol-3-ium bromide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 以47%的产率得到Tetraethyl 6,12-bis(2,4,5-trimethoxyphenyl)-3,9-diazapentacyclo[6.4.0.02,7.04,11.05,10]dodecane-1,5,7,11-tetracarboxylate
  参考文献：
  名称：

  Triplet phenacylimidazoliums-catalyzed photocycloaddition of 1,4-dihydropyridines: An experimental and theoretical study

  摘要：

  The photocycloadditions of 1,4-dihydropyridines (DHPs) were achieved by using phenacylimidazoliums (Plms) as photosensitizers. Irradiation of DHPs 3a-g in the presence of Plms 1a-e and 2 performed an efficient formation of 3,9-diazatetraasteranes in shorter times under a lower power lamp. The mechanism of photocycloaddition catalyzed by Plm was studied by laser flash photolysis and theoretical OFT computation. These time-resolved results showed that the triplet excited states of Plms were generated with high efficiency and detected by their characteristic ultraviolet absorptions, which were quenched by DHP at almost diffusion controlled rate. Theoretical studies suggest that Plm is involved in the photocycloaddition process through the (3)(DHP center dot center dot center dot Plm)* triplet complexes and assists the stabilization of intermediates. All subsequent steps are predicted to be favorable and exothermic, leading to the cage dimers. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2012.05.013

文献信息

• Triplet phenacylimidazoliums-catalyzed photocycloaddition of 1,4-dihydropyridines: An experimental and theoretical study
  作者：Xiaohe Zhu、Weipeng Li、Hong Yan、Rugang Zhong

  DOI：10.1016/j.jphotochem.2012.05.013

  日期：2012.8

  The photocycloadditions of 1,4-dihydropyridines (DHPs) were achieved by using phenacylimidazoliums (Plms) as photosensitizers. Irradiation of DHPs 3a-g in the presence of Plms 1a-e and 2 performed an efficient formation of 3,9-diazatetraasteranes in shorter times under a lower power lamp. The mechanism of photocycloaddition catalyzed by Plm was studied by laser flash photolysis and theoretical OFT computation. These time-resolved results showed that the triplet excited states of Plms were generated with high efficiency and detected by their characteristic ultraviolet absorptions, which were quenched by DHP at almost diffusion controlled rate. Theoretical studies suggest that Plm is involved in the photocycloaddition process through the (3)(DHP center dot center dot center dot Plm)* triplet complexes and assists the stabilization of intermediates. All subsequent steps are predicted to be favorable and exothermic, leading to the cage dimers. (C) 2012 Elsevier B.V. All rights reserved.