1-Amino-2-methylcarbamoyl-anthrachinon | 75534-98-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-Amino-2-methylcarbamoyl-anthrachinon
• 英文别名: 1-amino-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid methylamide；1-Amino-9,10-dioxo-N-methyl-9,10-dihydro-anthracencarbamid-(2)；1-Amino-9,10-dioxo-9,10-dihydro-anthracen-2-carbonsaeure-methylamid；1-amino-N-methyl-9,10-dioxoanthracene-2-carboxamide
• CAS: 75534-98-4
• 化学式: C₁₆H₁₂N₂O₃
• 分子量: 280.283
• InChiKey: XLBHESQMTFYWIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  89.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 ammonium hydroxide 作用下， 生成 1-Amino-2-methylcarbamoyl-anthrachinon
  参考文献：
  名称：

  DE604279

  摘要：

  公开号：

文献信息

• Production of 1-aminoanthraquinone-2-carboxylic acid amides
  申请人：BASF AG

  公开号：US02717898A1

  公开（公告）日：1955-09-13

  1 - Aminoanthraquinone - 2 - carboxylic acid amides and also certain oxdiazoles, hydroxypyrimidines, imidazoles, thiazoles, and oxazoles are obtained by reacting 3,4-phthaloylisatoic acid anhydrides with amino compounds having at least one hydrogen atom attached to nitrogen, and, if desired, when the amino compound is a hydrazide, an amidine, or an aminoanthraquinone having in ortho-position to the amino group a further amino group or a mercapto or hydroxy group or a halogen atom, converting the products first obtained into oxdiazoles, hydroxypyrimidines, imidazoles, thiazoles, and oxazoles by splitting off water, ammonia, or hydrogen halide by heating or by treatment with sulphuric acid, oleum, chlorsulphonic acid, arylsulphonic acids, phosphoric acid, phosphorus pentoxide, or thionyl chloride. The 3,4-phthaloylisatoic acid anhydride may be substituted, e.g. by halogen, hydroxy, alkoxy, nitro, acylamino, carbonamido, alkyl, or aryl, and benzene, pyridine, or triazole nuclei may also be attached. In examples, 3,4-phthaloylisatoic acid anhydride is reacted with (1) methylamine; (2) di-isobutylamine; (3) aniline; (4) monomethylaniline; (5) 1-amino-5-benzoylaminoanthraquinone; (6) 2-hydroxy-3-aminoanthraquinone, followed by heating with p-toluenesulphonic acid to give 2-(1-aminoanthraquinonyl - 2 -) anthraquinone - 21(N),31 - 4,5 - oxazole; (7) benzamidine, to give 1-aminoanthraquinone-2-carboxylic acid benzamidide, which on heating gives 2-phenyl-4-hydroxy-7,8-phthaloylquinazoline; (8) hydrazine, giving either 1-aminoanthraquinone-2-carboxylic acid hydrazide or N,N1-di-(1-aminoanthraquinone-2-carbonyl)-hydrazine and condensing the latter in presence of thionyl chloride to give di-(1-aminoanthraquinonyl-2) oxdiazole; (9) benzidine, tolidine, dianisidine, benzidine-3,31-dicarbonylic acid, or 2,21-diamino-4,41-dithiazolyl. Also in examples: (10) 3,4-phthaloyl-5-nitroisatoic anhydride is reacted with aniline; and (11) 3,4-phthaloyl-5-methoxy isatoic anhydride is reacted with hydrazine, benzidine, tolidine, or dianisidine; and (12) 3,4-phthaloyl-5-chlorisatoic anhydride is reacted with tolidine.

  1- 氨基蒽醌-2-羧酸酰胺以及某些噁二唑、羟基嘧啶、咪唑、噻唑和噁唑醇可通过将3,4-苯二甲酰异间苯二甲酸酐与至少有一个氢原子连接到氮的氨基化合物反应而得到，如果需要，当氨基化合物是酰肼，酰胺或在氨基团的邻位具有进一步氨基团或巯基或羟基或卤素原子的氨基蒽醌时，通过加热或用硫酸、油酸、氯磺酸、芳基磺酸、磷酸、五氧化二磷或亚磺酰氯处理，将最初得到的产物转化为噁二唑、羟基嘧啶、咪唑、噻唑和噁唑醇。3,4-苯二甲酰异间苯二甲酸酐可以被取代，例如通过卤素、羟基、烷氧基、硝基、酰胺基、碳酰胺基、烷基或芳基，还可以连接苯环、吡啶或三唑核。在示例中，3,4-苯二甲酰异间苯二甲酸酐与（1）甲胺；（2）二异丁基胺；（3）苯胺；（4）单甲基苯胺；（5）1-氨基-5-苯甲酰氨基蒽醌；（6）2-羟基-3-氨基蒽醌，随后与对甲苯磺酸加热，得到2-(1-氨基蒽醌基-2-)蒽醌-21（N），31-4,5-噁二唑；（7）苯甲酰胺，得到1-氨基蒽醌-2-羧酸苯甲酰胺，加热后得到2-苯基-4-羟基-7,8-苯二甲酰喹唑啉；（8）肼，得到1-氨基蒽醌-2-羧酸肼或N，N1-二（1-氨基蒽醌-2-羰基）-肼，并在亚磺酰氯存在下缩合后得到二（1-氨基蒽醌基-2）噁二唑；（9）苯二胺，甲苯二胺，二甲氧基苯二胺，苯二甲酸-3,31-二羧酸或2,21-二氨基-4,41-二噻唑基。在其他示例中：（10）3,4-苯二甲酰-5-硝基异间苯二甲酸酐与苯胺反应；（11）3,4-苯二甲酰-5-甲氧基异间苯二甲酸酐与肼，苯二胺，甲苯二胺或二甲氧基苯二胺反应；（12）3,4-苯二甲酰-5-氯异间苯二甲酸酐与甲苯二胺反应。