1-bromo-4-(ethylamino)anthracene-9,10-dione | 23873-67-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-bromo-4-(ethylamino)anthracene-9,10-dione
• 英文别名: 1-Bromo-4-(ethylamino)-9,10-anthracenedione
• CAS: 23873-67-8
• 化学式: C₁₆H₁₂BrNO₂
• 分子量: 330.181
• InChiKey: QKBWYRPXNDNVSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  1-(ethylamino)anthraquinone 在 氢溴酸 、 双氧水 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以85%的产率得到1-bromo-4-(ethylamino)anthracene-9,10-dione
  参考文献：
  名称：

  Efficient, facile metal free protocols for the bromination of commercially important deactivated aminoanthracene-9,10-diones

  摘要：

  Highly efficient, mild synthetic protocols were developed for the oxidative bromination of deactivated aminoanthracene-9,10-diones by using H2O2-HBr and m-CPBA-HBr in methanolic medium. Both the protocols offer excellent bromine atom economy, good conversion (100%) along with high yield (82-93%) and high purity of desired product. The N-alkylated amines undergo regio-selective bromination to give selective p-bromo product. The commercial availability of all the starting materials, simple reaction procedure and ease of work up, and easily amenable for scale up demonstrated commercial feasibility of both the protocols. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2017.05.078

文献信息

• Anthrapyridone compounds and their production process
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0353031A2

  公开（公告）日：1990-01-31

  An anthrapyridone compound of the following formula (I), which is useful for coloring synthetic resins: wherein Q is -NH₂, -NHCH₃ or -NHCOZ where Z is phenyl or alkyl which may be substituted; X₁, X₂ and X₃ are each hydrogen, halogen, alkyl, alkoxy, hydroxy, -NHCOR¹, -CONR²R³, -COR⁴, -COOR⁵, -SO₂R⁶ or -SO₂NR⁷R⁸ where R¹ and R⁴ are each C₁₋₄ alkyl R² and R³ are each hydrogen or C₁₋₄ alkyl, R⁵ and R⁶ are each alkyl or hydroxyalkyl and R⁷ and R⁸ are each hydrogen or C₁₋₄ alkyl, with proviso that when Q is -NHCH₃, X₁, X₂ and X₃ are each hydrogen, halogen, alkoxy, hydroxy, -NHCOR¹, -CONR²R³, -COR⁴, -COOR⁵, -SO₂R⁶ or -SO₂NR⁷R⁸. Process for producing the anthrapyridone compound is also provided.

  一种下式(I)的蒽吡啶酮化合物，可用于合成树脂着色： 其中 Q 为 -NH₂、-NHCH₃ 或 -NHCOZ，Z 为苯基或可被取代的烷基；X₁、X₂ 和 X₃ 各为氢、卤素、烷基、烷氧基、羟基、-NHCOR¹、-CONR²R³、-COR⁴、-COR⁵、-SO₂R⁶ 或 -SOR⁸ 其中 R¹ 和 R⁴ 各为 C₁₋₄ 烷基 R² 和 R³ 各为氢或 C₁₋₄ 烷基、R⁵和R⁶各自为烷基或羟烷基，R⁷和R⁸各自为氢或C₁₋₄烷基，但当Q为-NHCH₃时、X₁、X₂和X₃各自为氢、卤素、烷氧基、羟基、-NHCOR¹、-CONR²R³、-COR⁴、-COR⁵、-SO₂R⁶或-SO₂NR⁷R⁸。 还提供了生产蒽吡啶酮化合物的工艺。
• Verfahren zur Herstellung kationischer Anthrachinon-Farbstoffe
  申请人：BAYER AG

  公开号：EP0014899B1

  公开（公告）日：1981-10-21
• US4296044A
  申请人：——

  公开号：US4296044A

  公开（公告）日：1981-10-20
• US5183892A
  申请人：——

  公开号：US5183892A

  公开（公告）日：1993-02-02
• Efficient, facile metal free protocols for the bromination of commercially important deactivated aminoanthracene-9,10-diones
  作者：Vilas V. Patil、Eknath M. Gayakwad、Khushbu P. Patel、Ganapati S. Shankarling

  DOI：10.1016/j.tetlet.2017.05.078

  日期：2017.6

  Highly efficient, mild synthetic protocols were developed for the oxidative bromination of deactivated aminoanthracene-9,10-diones by using H2O2-HBr and m-CPBA-HBr in methanolic medium. Both the protocols offer excellent bromine atom economy, good conversion (100%) along with high yield (82-93%) and high purity of desired product. The N-alkylated amines undergo regio-selective bromination to give selective p-bromo product. The commercial availability of all the starting materials, simple reaction procedure and ease of work up, and easily amenable for scale up demonstrated commercial feasibility of both the protocols. (C) 2017 Elsevier Ltd. All rights reserved.