1-Amino-2-(3-oxo-hex-1-ynyl)-anthraquinone | 159971-58-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-Amino-2-(3-oxo-hex-1-ynyl)-anthraquinone
• 英文别名: 1-Amino-2-(3-oxohex-1-yn-1-yl)anthracene-9,10-dione；1-amino-2-(3-oxohex-1-ynyl)anthracene-9,10-dione
• CAS: 159971-58-1
• 化学式: C₂₀H₁₅NO₃
• 分子量: 317.344
• InChiKey: KFRODYRHFGPJMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  77.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-Amino-2-(3-oxo-hex-1-ynyl)-anthraquinone 在 potassium dichromate 、 硫酸 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 溶剂黄146 为溶剂， 生成 6,11-dioxo-2H-naphtho[2,3-g]indazole-3-carboxylic acid
  参考文献：
  名称：

  An unusual direction of the Richter synthesis. 1H-naphtho[2,3-g]indazole-6,11-diones

  摘要：

  Diazotization of 2-acetylenic derivatives of 1-aminoanthraquinone followed by intramolecular cyclization leads to the formation is good yields of 1H-3-acyl- or 1H-3-(1,1-dichloroalkyl)naphtho[2,3-g]indazole-6,11-diones, rather than 3-substituted 4-hydroxynahtho[2,3-h]cinnoline-7,1 2-diones, the normal Richter synthesis products.

  DOI：

  10.1016/s0040-4039(00)73485-x

文献信息

• Reaction of 1-amino-2-phenylethynyl-and 2-acylethynyl-1-amino-9,10-anthraquinones with HNO2. Synthesis of 1H-3-acylnaphtho[2,3-g]indazole-6,11-diones
  作者：I. D. Ivanchikova、L. G. Fedenok、M. S. Shvartsberg

  DOI：10.1007/bf02495357

  日期：1997.1

  The reactions of 1-amino-2-phenylethynyl- and 2-acylethynyl-1-amino-9,10-anthraquinones with HNO2 in a mixture of dioxane and a mineral acid at 20 degrees C were studied. Under these conditions, 2-alkynyl-1-amino-9,10-anthraquinones, irrespective of the structure of the C=CR substituent, are cyclized into 3-substituted 1H-naphtho[2,3-g]indazole-6,11-diones. The nature of the acetylenic group in the initial compound and the choice of the mineral acid determine the structure of the substituent in position 3 of the product (1,1-dichloroalkyl or acyl) but have no effect on the regiospecificity of cyclization.