2-bromo-3-(N-ethylamino)-1,4-naphthoquinone | 70979-68-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-bromo-3-(N-ethylamino)-1,4-naphthoquinone
• 英文别名: 2-bromo-3-ethylamino-1,4-naphthoquinone；2-Bromo-3-(ethylamino)naphthalene-1,4-dione
• CAS: 70979-68-9
• 化学式: C₁₂H₁₀BrNO₂
• 分子量: 280.121
• InChiKey: NIBLKUNVOUQENZ-UHFFFAOYSA-N

物化性质

• 沸点：
  350.5±42.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2-bromo-3-(N-ethylamino)-1,4-naphthoquinone 在 硫酸 作用下， 生成 2-Bromo-3-(N-acetylethylamino)-1,4-naphthoquinone
  参考文献：
  名称：

  Ignatovich, L. G.; Dregeris, Ya. Ya.; Freimanis, Ya. F., Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, p. 520 - 526

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-二溴-1,4-萘醌 、 乙胺 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以70%的产率得到2-bromo-3-(N-ethylamino)-1,4-naphthoquinone
  参考文献：
  名称：

  Ignatovich, L. G.; Dregeris, Ya. Ya.; Freimanis, Ya. F., Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, p. 520 - 526

  摘要：

  DOI：

文献信息

• Synthesis, characterization and molecular structures of homologated analogs of 2-bromo-3-(n-alkylamino)-1,4-napthoquinone
  作者：Sunita Salunke-Gawali、Omkar Pawar、Milind Nikalje、Rishikesh Patil、Thomas Weyhermüller、Vedavati G. Puranik、V. Badireenath Konkimalla

  DOI：10.1016/j.molstruc.2013.10.016

  日期：2014.1

  Four analogues of 2-bromo-3-(n-alkylamino)-1,4-napthoquinone (where n-alkyl is methyl in L-1Br, ethyl in L-2Br, propyl in L-3Br and butyl in L-4Br) are synthesized and characterized. A reaction mechanism is proposed for the formation of L-1 Br to L-4Br from the starting material 2,3-dibromo-1,4-naphthoquinone. The v(N-H) frequency in the FT-IR spectra is affected by the intramolecular hydrogen bonding in L-1Br to L-4Br and is observed similar to 3267 cm(-1) in L-2Br. A shift of similar to 25 cm(-1) is observed in the v(C-Br) frequency in all the compounds as compared to 2,3-dibromo-1,4-naphthoquinone (627 cm(-1)). A broad charge transfer band is observed between 400 and 600 nm in the UV-Vis spectra, which imparts red colour to all the compounds. Molecular structures of L-2Br and L-3Br were studied by single crystal X-ray diffraction studies. Molecules of L-2Br crystallize in Pca2(1), whereas the molecule L-3Br crystallizes in the P-1 space group. Molecules of L-2Br forms a polymeric chain through N-H...O interaction and forms beautiful butterfly like arrangement of molecules when viewed down the 'a' axis. Ladder like polymeric chain of molecules is observed in L-3Br via C-H...O and N-H...O interactions. Every alternating neighbouring chains of L-3Br, show pi-pi stacking interactions between the quinonoid rings of the molecules, however this interaction is not observed in L-2Br. (C) 2013 Elsevier B.V. All rights reserved.