methyl 3-(dodeca-1,3-diynyl)-4-[(3-phenyl-3-ethyl)triazene-1-yl]benzoate | 1197991-01-7

• 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: methyl 3-(dodeca-1,3-diynyl)-4-[(3-phenyl-3-ethyl)triazene-1-yl]benzoate
• 英文别名: methyl 3-dodeca-1,3-diynyl-4-[(N-ethylanilino)diazenyl]benzoate
• CAS: 1197991-01-7
• 化学式: C₂₈H₃₃N₃O₂
• 分子量: 443.589
• InChiKey: JWZDQKGHYZLPGC-UHFFFAOYSA-N

物化性质

• 沸点：
  581.3±60.0 °C(predicted)
• 密度：
  0.99±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  54.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-(dodeca-1,3-diynyl)-4-[(3-phenyl-3-ethyl)triazene-1-yl]benzoate 在 氢溴酸 、 碘 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 17.75h， 生成 methyl 3-iodo-2-octylthieno[3,2-C]cinnoline-8-carboxylate
  参考文献：
  名称：

  Study of cyclyzation of o-(1-Alkynyl)- and o-(1,3-Butadiynyl)aryltriazenes under the action of acids

  摘要：

  The investigation of Richter cyclization of o-(1-alkynyl)- and o-(1,3-butadiynyl)arenediazonium salts generated by acid cleavage of triazenes was carried out by the methods of NMR and ESI MS (Electrospray Ionization Mass Spectrometry). The effect was shown of the substituents at the carbon atom of the triple bond and in the aromatic ring, of the solvent, temperature, and the reagents ratio on the rate of the cyclization and the yield of its products, 4-bromo-3-alkyl- and 4-bromo-3-ethynylcinnolines; the conditions of their synthesis were optimized. The possibility to use 4-bromo-3-ethynylcinnolines as substrates of electrophilic cyclization was demonstrated.

  DOI：

  10.1134/s1070428012110048
• 作为产物：
  描述：

  methyl 3-iodo-4-(3-ethyl-3-phenyltriaz-1-ene-1-yl)benzoate 、 dodeca-1,3-diyne 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 反应 8.0h， 以95%的产率得到methyl 3-(dodeca-1,3-diynyl)-4-[(3-phenyl-3-ethyl)triazene-1-yl]benzoate
  参考文献：
  名称：

  A short route to 3-alkynyl-4-bromo(chloro)cinnolines by Richter-type cyclization of ortho-(dodeca-1,3-diynyl)aryltriaz-1-enes

  摘要：

  Cleavage of ortho-(dodeca-1,3-diynyl)triazenes in HCl or HBr medium and subsequent cyclization of the resulting diazonium salts is investigated. In the absence of a strong electron-withdrawing substituent, the reaction affords 3-alkynyl-4-bromo(chloro)cinnolines as the only product. A methoxycarbonyl group promotes hydrolysis of 4-halocinnolines which results in the formation of by-products: furo[3,2-c]cinnoline and cinnolinone. Substitution of bromine in 3-(alk-1-ynyl)-4-bromocinnolines is achieved with methylamine, Na2S and ethynylbenzene affording pyrrolo[3,2-c]cinnoline, thieno[3,2-c]cinnoline and 3,4-diethynylcinnoline, respectively. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.08.103

文献信息

• A short route to 3-alkynyl-4-bromo(chloro)cinnolines by Richter-type cyclization of ortho-(dodeca-1,3-diynyl)aryltriaz-1-enes
  作者：Olga V. Vinogradova、Viktor N. Sorokoumov、Irina A. Balova

  DOI：10.1016/j.tetlet.2009.08.103

  日期：2009.11

  Cleavage of ortho-(dodeca-1,3-diynyl)triazenes in HCl or HBr medium and subsequent cyclization of the resulting diazonium salts is investigated. In the absence of a strong electron-withdrawing substituent, the reaction affords 3-alkynyl-4-bromo(chloro)cinnolines as the only product. A methoxycarbonyl group promotes hydrolysis of 4-halocinnolines which results in the formation of by-products: furo[3,2-c]cinnoline and cinnolinone. Substitution of bromine in 3-(alk-1-ynyl)-4-bromocinnolines is achieved with methylamine, Na2S and ethynylbenzene affording pyrrolo[3,2-c]cinnoline, thieno[3,2-c]cinnoline and 3,4-diethynylcinnoline, respectively. (C) 2009 Elsevier Ltd. All rights reserved.
• Study of cyclyzation of o-(1-Alkynyl)- and o-(1,3-Butadiynyl)aryltriazenes under the action of acids
  作者：N. A. Danilkina、E. G. Gorbunova、V. N. Sorokoumov、I. A. Balova

  DOI：10.1134/s1070428012110048

  日期：2012.11

  The investigation of Richter cyclization of o-(1-alkynyl)- and o-(1,3-butadiynyl)arenediazonium salts generated by acid cleavage of triazenes was carried out by the methods of NMR and ESI MS (Electrospray Ionization Mass Spectrometry). The effect was shown of the substituents at the carbon atom of the triple bond and in the aromatic ring, of the solvent, temperature, and the reagents ratio on the rate of the cyclization and the yield of its products, 4-bromo-3-alkyl- and 4-bromo-3-ethynylcinnolines; the conditions of their synthesis were optimized. The possibility to use 4-bromo-3-ethynylcinnolines as substrates of electrophilic cyclization was demonstrated.