(E,E,E)-1,6-bis(2-thienyl)-3-nitro-1,3,5-hexatriene | 401814-56-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (E,E,E)-1,6-bis(2-thienyl)-3-nitro-1,3,5-hexatriene
• 英文别名: 2-[(1E,3E,5E)-4-nitro-6-thiophen-2-ylhexa-1,3,5-trienyl]thiophene
• CAS: 401814-56-0
• 化学式: C₁₄H₁₁NO₂S₂
• 分子量: 289.379
• InChiKey: QECLSBRNDMQBEK-XAICMWRQSA-N

物化性质

• 沸点：
  497.7±45.0 °C(Predicted)
• 密度：
  1.330±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E,E,E)-1,6-bis(2-thienyl)-3-nitro-1,3,5-hexatriene 以 氘代氯仿 为溶剂， 生成 cis-5,6-bis(2-thienyl)-2-nitro-1,3-cyclohexadiene
  参考文献：
  名称：

  From 3,4-dinitrothiophene to 1,2-diaryl-4-nitrobenzenes through ( E , E , E )-1,6-diaryl-3-nitro-1,3,5-hexatrienes

  摘要：

  The reactions between 1,2-bis(diethylamino)-2,3-dinitro-1,3-butadiene, easily obtainable by ring-opening of 3,4-dinitrothiophene with diethylamine, and arylmethylmagnesium chlorides in THF at 0 degreesC furnished good yields of (E,E,E)-1,6-diaryl-3-nitro-1,3,5-hexatrienes. To explain the formation of the hexatrienes, a mechanism is advanced which involves, in particular, tautomerisation of the intermediate 1,6-diaryl-3,4-dinitro-2,4-hexadienes followed by base-induced elimination of nitrous acid. The electrocyclic disrotatory conversion of the hexatrienes into the corresponding 5,6-diaryl-2-nitro-1,3-cyclohexadienes was analysed by H-1 NMR spectroscopy and exploited for the high-yielding synthesis of 1,2-diaryl-4-nitrobenzenes employing, as oxidants, either DDQ or iodine in the presence of cyclohexene oxide as HI scavenger. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00898-5
• 作为产物：
  描述：

  magnesium,2-methanidylthiophene,chloride 、 (E,E)-1,4-bis(diethylamino)-2,3-dinitro-1,3-butadiene 在 盐酸 作用下， 以 四氢呋喃 、 xylene 、 二氯甲烷 为溶剂， 反应 0.25h， 以41%的产率得到(E,E,E)-1,6-bis(2-thienyl)-3-nitro-1,3,5-hexatriene
  参考文献：
  名称：

  From 3,4-dinitrothiophene to 1,2-diaryl-4-nitrobenzenes through ( E , E , E )-1,6-diaryl-3-nitro-1,3,5-hexatrienes

  摘要：

  The reactions between 1,2-bis(diethylamino)-2,3-dinitro-1,3-butadiene, easily obtainable by ring-opening of 3,4-dinitrothiophene with diethylamine, and arylmethylmagnesium chlorides in THF at 0 degreesC furnished good yields of (E,E,E)-1,6-diaryl-3-nitro-1,3,5-hexatrienes. To explain the formation of the hexatrienes, a mechanism is advanced which involves, in particular, tautomerisation of the intermediate 1,6-diaryl-3,4-dinitro-2,4-hexadienes followed by base-induced elimination of nitrous acid. The electrocyclic disrotatory conversion of the hexatrienes into the corresponding 5,6-diaryl-2-nitro-1,3-cyclohexadienes was analysed by H-1 NMR spectroscopy and exploited for the high-yielding synthesis of 1,2-diaryl-4-nitrobenzenes employing, as oxidants, either DDQ or iodine in the presence of cyclohexene oxide as HI scavenger. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00898-5