2,5-bis[bis(3-methoxycarbonyl-1-azulenyl)methyl]thiophene | 1024656-16-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: 2,5-bis[bis(3-methoxycarbonyl-1-azulenyl)methyl]thiophene
• CAS: 1024656-16-3
• 化学式: C₅₄H₄₀O₈S
• 分子量: 848.973
• InChiKey: IYFRNNJGJIEFBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.67
• 重原子数：
  63.0
• 可旋转键数：
  10.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  105.2
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  2,5-噻吩二甲醛 、 甲基1-薁羧酸酯 在 盐酸 、 溶剂黄146 作用下， 反应 2.0h， 以97%的产率得到2,5-bis[bis(3-methoxycarbonyl-1-azulenyl)methyl]thiophene
  参考文献：
  名称：

  An efficient preparation and spectroscopic and electrochemical properties of quinodimethane derivatives with four 3-(methoxycarbonyl)azulen-1-yl groups

  摘要：

  Reaction of methyl 1-azuienecarboxylate (8) with terephthalaldehyde (9) in acetic acid in the presence of hydrochloric acid at 25 degrees C for 2 It gives 1,4-bis[bis(3-methoxycarbonyl-1-azulenyl)methyl]benzene (12), in 93% yield, which upon oxidation with 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) in dichloromethane in the presence of hexafluorophosphoric acid at 25 degrees C for I h affords the dicarbenium-ion compound 15 in 94% yield. Furthermore, reduction of 15 with zinc powder in a mixed solvent of acetonitrile and chloroform at 25 T for I h yields the target quinodi-methane 18 in 90% yield. Similarly, as in the case of 18, the quinoid compounds 19 and 20 can be derived from the dicarbenium-ion compounds 16 and 17, quantitatively. A facile preparation as well as spectroscopic and electrochemical properties of 15-20 is reported. (c) 2008 Elsevier Ltd. All fights reserved.

  DOI：

  10.1016/j.tet.2008.02.012