2-amino-3-(2-bromophenyl)-1,4-naphthoquinone | 1567382-74-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-amino-3-(2-bromophenyl)-1,4-naphthoquinone
• 英文别名: 2-amino-3-(2-bromophenyl)naphthalene-1,4-dione；2-Amino-3-(2-bromophenyl)naphthalene-1,4-dione
• CAS: 1567382-74-4
• 化学式: C₁₆H₁₀BrNO₂
• 分子量: 328.165
• InChiKey: NEYBDQSKUHVUCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-3-(2-bromophenyl)-1,4-naphthoquinone 在 copper(l) iodide 、 1,10-菲罗啉 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.3h， 以85%的产率得到5H-benzo[b]carbazole-6,11-dione
  参考文献：
  名称：

  Transition metal mediated selective C vs N arylation of 2-aminonaphthoquinone and its application toward the synthesis of benzocarbazoledione

  摘要：

  Selective C vs N-arylation of 2-aminonaphthoquinone was achieved using different transition metal salts and arylboronic acids. Mn(OAc)(3)center dot 2H(2)O provided C-arylated product whereas NiCl2 center dot 6H(2)O and Cu (OAc)(2)center dot H2O provided N-mono arylated and N,N-diarylated products respectively. Usefulness of the C and N arylated product was demonstrated by converting it into benzocarbazoledione. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2017.10.075
• 作为产物：
  描述：

  2-氨基-1,4-萘醌 、 2-溴苯基硼酸 在 manganese(III) triacetate dihydrate 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以43%的产率得到2-amino-3-(2-bromophenyl)-1,4-naphthoquinone
  参考文献：
  名称：

  Transition metal mediated selective C vs N arylation of 2-aminonaphthoquinone and its application toward the synthesis of benzocarbazoledione

  摘要：

  Selective C vs N-arylation of 2-aminonaphthoquinone was achieved using different transition metal salts and arylboronic acids. Mn(OAc)(3)center dot 2H(2)O provided C-arylated product whereas NiCl2 center dot 6H(2)O and Cu (OAc)(2)center dot H2O provided N-mono arylated and N,N-diarylated products respectively. Usefulness of the C and N arylated product was demonstrated by converting it into benzocarbazoledione. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2017.10.075

文献信息

• Aryl-Free Radical-Mediated Oxidative Arylation of Naphthoquinones Using <i>o</i>-Iodoxybenzoic Acid and Phenylhydrazines and Its Application toward the Synthesis of Benzocarbazoledione
  作者：Pravin Patil、Abhay Nimonkar、Krishnacharya G. Akamanchi

  DOI：10.1021/jo500131h

  日期：2014.3.7

  Oxidative arylation of naphthoquinones has been developed through combination of o-iodoxybenzoic acid with arylhydrazines under mild conditions at open atmosphere. Arylated naphthoquinones with different electronic properties were obtained in moderate to good yields. The postulated radical mediated mechanism is supported by radical trapping experiments. Developed protocol for direct arylation of naphthoquinones has been extended toward short, high yielding, and an effective synthesis of antitumor-antibiotic precursor such as benzocarbazoledione.