3-diethylamino-5-phenylethynyl-1,4-naphthoquinone | 110574-62-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-diethylamino-5-phenylethynyl-1,4-naphthoquinone
• 英文别名: 2-(diethylamino)-8-(2-phenylethynyl)naphthalene-1,4-dione
• CAS: 110574-62-4
• 化学式: C₂₂H₁₉NO₂
• 分子量: 329.398
• InChiKey: RJXWQEAECDNFNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-diethylamino-5-phenylethynyl-1,4-naphthoquinone 在 吡啶 、 一水合肼 作用下， 反应 8.0h， 以59%的产率得到3-benzyl-9-diethylaminobenzo[de]cinnolin-7-one
  参考文献：
  名称：

  摘要：

  Condensation of 5-arylethynyl-3-diethylaminonaphthoquinones with NH2NH2 afford 3-benzyl-9-diethylaminobenzo[de]cinnolin-7-ones. The substituents in the phenyl ring have a pronounced effect on the reaction time and the yields of benzocinnolinones and by-products. The replacement of the arylethynyl substituent in the starting naphthoquinone by the 3-hydroxyalk-1-ynyl group leads to a change in the direction of cyclization resulting in substituted naphtho[1,8-cd]-1,2-diazepin-8-ones as condensation products.

  DOI：

  10.1023/a:1013007223337
• 作为产物：
  描述：

  苯乙炔 、 3-diethylamino-5-iodo-1,4-naphthoquinone 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二乙胺 作用下， 反应 1.5h， 以74%的产率得到3-diethylamino-5-phenylethynyl-1,4-naphthoquinone
  参考文献：
  名称：

  Synthesis of 5-ethynyl-l,4-naphthoquinone and its derivatives

  摘要：

  DOI：

  10.1007/bf00953338

文献信息

• An unknown route of cyclocondensation of peri-acetylenylquinones with hydrazine
  作者：Mark S Shvartsberg、Irena D Ivanchikova

  DOI：10.1016/s0040-4039(99)02151-6

  日期：2000.1

  Cyclocondensation of 3-diethylamino-5-phenylethynyl-1,4-naphthoquinone with NH2NH2 resulting in the closure of a pyridazine ring is reported. This hydrazine condensation was unknown for peri-acetylenic derivatives of polycyclic quinones. (C) 2000 Elsevier Science Ltd. All rights reserved.
• SHVARTSBERG M. S.; MOROZ A. A.; IVASHKINA N. V.; CHEREPANOV S. B., IZV. AN CCCP. CEP. XIM.,(1986) N 11, 2485-2491
  作者：SHVARTSBERG M. S.、 MOROZ A. A.、 IVASHKINA N. V.、 CHEREPANOV S. B.

  DOI：——

  日期：——
• Synthesis of 5-ethynyl-l,4-naphthoquinone and its derivatives
  作者：M. S. Shvartsberg、A. A. Moroz、N. V. Ivashkina、S. B. Cherepanov

  DOI：10.1007/bf00953338

  日期：1986.11
• ——
  作者：I. D. Ivanchikova、R. N. Myasnikova、M. S. Shvartsberg

  DOI：10.1023/a:1013007223337

  日期：——

  Condensation of 5-arylethynyl-3-diethylaminonaphthoquinones with NH2NH2 afford 3-benzyl-9-diethylaminobenzo[de]cinnolin-7-ones. The substituents in the phenyl ring have a pronounced effect on the reaction time and the yields of benzocinnolinones and by-products. The replacement of the arylethynyl substituent in the starting naphthoquinone by the 3-hydroxyalk-1-ynyl group leads to a change in the direction of cyclization resulting in substituted naphtho[1,8-cd]-1,2-diazepin-8-ones as condensation products.