4-bromo-3-(dec-1-ynyl)-6-cinnolinecarboxylic acid methyl ester | 1197991-05-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-bromo-3-(dec-1-ynyl)-6-cinnolinecarboxylic acid methyl ester
• 英文别名: methyl 4-bromo-3-(dec-1-yn-1-yl)-6-cinnolinecarboxylate；Methyl 4-bromo-3-dec-1-ynylcinnoline-6-carboxylate
• CAS: 1197991-05-1
• 化学式: C₂₀H₂₃BrN₂O₂
• 分子量: 403.319
• InChiKey: KVTYSIALBHBTSO-UHFFFAOYSA-N

物化性质

• 熔点：
  137-139 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  520.7±60.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-bromo-3-(dec-1-ynyl)-6-cinnolinecarboxylic acid methyl ester 在 sodium sulfide nonahydrate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以51%的产率得到2-octylthieno[3,2-c]cinnoline-8-carboxylic acid
  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
• 作为产物：
  描述：

  dodeca-1,3-diyne 在 copper(l) iodide 、 四(三苯基膦)钯 、 氢溴酸 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 0.25h， 生成 Methyl 3-dodeca-1,3-diynylbenzoate 、 4-bromo-3-(dec-1-ynyl)-6-cinnolinecarboxylic acid methyl ester
  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

文献信息

• 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.
• 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.