2-bromo-3-propylamino-1,4-naphthoquinone | 70979-69-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-bromo-3-propylamino-1,4-naphthoquinone
• 英文别名: 2-Brom-3-propylamino-α-naphthochinon；2-Bromo-3-(propylamino)naphthalene-1,4-dione
• CAS: 70979-69-0
• 化学式: C₁₃H₁₂BrNO₂
• 分子量: 294.148
• InChiKey: JTJTVRCNKBHKNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  正丙胺 、 2,3-二溴-1,4-萘醌 以 二氯甲烷 为溶剂， 反应 24.0h， 以78.1%的产率得到2-bromo-3-propylamino-1,4-naphthoquinone
  参考文献：
  名称：

  Synthesis, characterization and molecular structures of homologated analogs of 2-bromo-3-(n-alkylamino)-1,4-napthoquinone

  摘要：

  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.

  DOI：

  10.1016/j.molstruc.2013.10.016

文献信息

• One-Step Synthesis of 1,2,3,4-Tetrahydrobenzo(g)quinazoline-5,10-dione Derivatives from Vitamin K3.
  作者：Shunsaku OHTA、Yasunari HINATA、Masayuki YAMASHITA、Ikuo KAWASAKI、Yoko JINDA、Shinobu HORIE

  DOI：10.1248/cpb.42.1730

  日期：——

  The reactions of 2-halogenonaphthoquinones (5, 13, 14 and 15) and 2-methyl-1, 4-naphthoquinone (20; vitamin K3) with primary and secondary amines were examined. 1, 3-Dialkyl-1, 2, 3, 4-tetrahydrobenzo[g]quinazoline-5, 10-diones (9) were obtained in moderate yields by treating 20 with formaldehyde in primary amines. A plausible reaction path-way is also presented.

  对2-卤代萘醌（5、13、14和15）和2-甲基-1,4-萘醌（20；维生素K3）与一级和二级胺的反应进行了研究。通过在一级胺中用甲醛处理20，获得了1,3-二烷基-1,2,3,4-四氢苯并[g]喹唑啉-5,10-二酮（9），产率适中。同时也提出了一个合理的反应路径。
• Chemoselective Substitution Reaction of 2-Bromo-3-methoxy-1,4-naphthoquinone
  作者：Bryanne L. Stills、Carolyn B. Lauzon、Tetsuo Otsuki

  DOI：10.1246/cl.2002.306

  日期：2002.3

  Chemoselective substitution reactions of 2-bromo-3-methoxy-1,4-naphthoquinone were studied here. In the reactions of 2-bromo-3-methoxy-1,4-naphthoquinone with a variety of alkylamines, 2-alkylamino-3-bromo-1,4-naphthoquinones resulted in high yields. Alkylthiols, on the other hand, were found to form 2-alkylthio-3-methoxy-1,4-naphthoquinones in their reactions with 2-bromo-3-methoxy-1,4-naphthoquinone in the presence of an amine.

  本文研究了 2-溴-3-甲氧基-1,4-萘醌的化学选择性取代反应。在 2-溴-3-甲氧基-1,4-萘醌与多种烷基胺的反应中，2-烷基氨基-3-溴-1,4-萘醌的产率很高。另一方面，烷基硫醇在胺的存在下与 2-溴-3-甲氧基-1,4-萘醌反应生成 2-烷硫基-3-甲氧基-1,4-萘醌。
• OERIU, Pharmazie, 1961, vol. 16, p. 266 - 272
  作者：OERIU

  DOI：——

  日期：——
• 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.