2-bromo-3-butylamino-1,4-naphthoquinone | 18690-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-bromo-3-butylamino-1,4-naphthoquinone
• 英文别名: 2-Brom-3-butylamino-1,4-naphthochinon；2-Brom-3-butylamino-naphthochinon-1,4；2-Bromo-3-(butylamino)naphthalene-1,4-dione
• CAS: 18690-84-1
• 化学式: C₁₄H₁₄BrNO₂
• 分子量: 308.175
• InChiKey: NSZIIDLIBOSHOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  2-bromo-3-butylamino-1,4-naphthoquinone 、 2-溴苯基硼酸 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 四(三苯基膦)钯 、 2-二环己基磷-2',6'-二异丙氧基-1,1'-联苯 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以38 mg的产率得到5-butyl-5H-benzo[b]carbazole-6,11-dione
  参考文献：
  名称：

  One-Pot Palladium-Catalyzed Synthesis of Benzo[b]carbazolediones

  摘要：

  A palladium-catalyzed one-pot reaction for the synthesis of benzo[b]carbazolediones is described which proceeds by amination of 2,3-dibromonaphthoquinone, Suzuki cross-coupling with (2-bromophenyl)boronic acid, and subsequent intramolecular C-N Buchwald-Hartwig cyclization with amines.

  DOI：

  10.1055/s-0035-1560212
• 作为产物：
  描述：

  2,3-二溴-1,4-萘醌 、 正丁胺 以 水 为溶剂， 反应 6.0h， 生成 2-bromo-3-butylamino-1,4-naphthoquinone
  参考文献：
  名称：

  One-Pot Palladium-Catalyzed Synthesis of Benzo[b]carbazolediones

  摘要：

  A palladium-catalyzed one-pot reaction for the synthesis of benzo[b]carbazolediones is described which proceeds by amination of 2,3-dibromonaphthoquinone, Suzuki cross-coupling with (2-bromophenyl)boronic acid, and subsequent intramolecular C-N Buchwald-Hartwig cyclization with amines.

  DOI：

  10.1055/s-0035-1560212

文献信息

• Synthesis of some 1,4-naphthoquinones and reactions relating to their use in the study of bacterial growth inhibition
  作者：R. F. Silver、H. L. Holmes

  DOI：10.1139/v68-309

  日期：1968.6.1

  A series of 107 1,4-naphthoquinones and related products has been synthesized to study their mode of action in bacterial growth inhibition. The in vitro reactions of a number of these with aniline, n-butylamine, sodium methoxide, and an n-buthanethiol–triethylamine mixture have been examined. A series of epoxides of C-2 monosubstituted and C-2,C-3 disubstituted 1,4-naphthoquinones has been synthesized and their reactions with amines, thiols, and halogen acids have been studied. The ultraviolet absorption maxima of many of these quinones are also tabulated.

  合成了一系列107种1,4-萘醌和相关产物，以研究它们在抑制细菌生长中的作用方式。已经研究了其中一些与苯胺、正丁胺、甲氧基钠和正丁硫醇-三乙胺混合物的体外反应。合成了一系列C-2单取代和C-2、C-3双取代1,4-萘醌的环氧化物，并研究了它们与胺、硫醇和卤素酸的反应。这些醌类化合物中许多的紫外吸收极值也已列出。
• 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。
• 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.
• One-Pot Palladium-Catalyzed Synthesis of Benzo[b]carbazolediones
  作者：Peter Langer、Hoang Do、Hung Tran、Lars Ohlendorf、Thang Ngo、Tuan Dang、Peter Ehlers、Alexander Villinger

  DOI：10.1055/s-0035-1560212

  日期：——

  A palladium-catalyzed one-pot reaction for the synthesis of benzo[b]carbazolediones is described which proceeds by amination of 2,3-dibromonaphthoquinone, Suzuki cross-coupling with (2-bromophenyl)boronic acid, and subsequent intramolecular C-N Buchwald-Hartwig cyclization with amines.