4,8-dibromo-3-(dec-1-ynyl)-6-methylcinnoline | 1197991-04-0

• 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: 4,8-dibromo-3-(dec-1-ynyl)-6-methylcinnoline
• 英文别名: 4,8-Dibromo-3-dec-1-ynyl-6-methylcinnoline
• CAS: 1197991-04-0
• 化学式: C₁₉H₂₂Br₂N₂
• 分子量: 438.205
• InChiKey: ORVFUYCSTZBBLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-[(2-bromo-6-dodeca-1,3-diynyl-4-methylphenyl)diazenyl]-N-ethylaniline 在 氢溴酸 作用下， 以 丙酮 为溶剂， 以75%的产率得到4,8-dibromo-3-(dec-1-ynyl)-6-methylcinnoline
  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.