1-amino-2-(3-hydroxyhex-1-ynyl)-9,10-anthraquinone | 335379-02-7

• 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-hydroxyhex-1-ynyl)-9,10-anthraquinone
• 英文别名: 1-amino-2-(3-hydroxyhex-1-ynyl)anthracene-9,10-dione
• CAS: 335379-02-7
• 化学式: C₂₀H₁₇NO₃
• 分子量: 319.36
• InChiKey: HEFDTUQKTSYVNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-amino-2-(3-hydroxyhex-1-ynyl)-9,10-anthraquinone 在 哌啶 作用下， 反应 18.0h， 以76.7%的产率得到2-(1-hydroxybutyl)naphtho[2,3-g]indole-6,11-dione
  参考文献：
  名称：

  摘要：

  When heated in piperidine, 1-amino-2-(3-hydroxyalk-1-ynyl)-9,10-anthraquinones undergo cyclization into 2-(1-hydroxyalkyl) naphthol 2,3-g]indole-6,11-diones. In contrast, 1-amino-2-(3-hydroxy-3-phenylpropynyl)-9,10-anthraquinone reacts with primary and secondary amines to give the corresponding 1-amino-2-(1-amino-2-benzoylvinyl)-9,10-anthraquinones, which undergo cyclization into 4-dialkylamino- or 4-alkylamino-2-phenylnaphtho[2,3-h]quinoline-7,12-diones. Heating of the starting phenylpropynol with Et3N causes its dehydrogenation and isomerization.

  DOI：

  10.1023/a:1013055106499
• 作为产物：
  描述：

  1-己炔-3-醇 、 1-amino-2-iodo-9,10-anthraquinone 在 bis-triphenylphosphine-palladium(II) chloride 吡啶 、 copper(l) iodide 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 0.25h， 以91.2%的产率得到1-amino-2-(3-hydroxyhex-1-ynyl)-9,10-anthraquinone
  参考文献：
  名称：

  摘要：

  When heated in piperidine, 1-amino-2-(3-hydroxyalk-1-ynyl)-9,10-anthraquinones undergo cyclization into 2-(1-hydroxyalkyl) naphthol 2,3-g]indole-6,11-diones. In contrast, 1-amino-2-(3-hydroxy-3-phenylpropynyl)-9,10-anthraquinone reacts with primary and secondary amines to give the corresponding 1-amino-2-(1-amino-2-benzoylvinyl)-9,10-anthraquinones, which undergo cyclization into 4-dialkylamino- or 4-alkylamino-2-phenylnaphtho[2,3-h]quinoline-7,12-diones. Heating of the starting phenylpropynol with Et3N causes its dehydrogenation and isomerization.

  DOI：

  10.1023/a:1013055106499

文献信息

• Two routes of heterocyclization of 2-alkynylanthraquinone-1-diazonium salts. The synthesis of 1 H -naphtho[2,3- h ]cinnoline-4,7,12-trione
  作者：Lidiya G Fedenok、Igor I Barabanov、Irena D Ivanchikova

  DOI：10.1016/s0040-4020(00)01101-7

  日期：2001.2

  The possibility of the heterocyclization of vic-alkynylanthraquinonediazonium salts with the formation of a 5- or 6-membered ring, depending on the reaction conditions, is established. The heterocyclization of 2-alkynyl-9,10-anthraquinone-1-diazonium salts to form 1H-naphtho[2,3-h]cinnoline-4,7,12-triones is reported.

  根据反应条件，确定了形成5-或6-元环的vic-炔基蒽醌二重氮盐杂环化的可能性。据报道2-炔基-9，10-蒽醌-1-重氮盐的杂环形成1 H-萘[2,3 - h ] cinnoline-4,7,12-三酮。
• ——
  作者：I. I. Barabanov、L. G. Fedenok、N. E. Polyakov、M. S. Shvartsberg

  DOI：10.1023/a:1013055106499

  日期：——

  When heated in piperidine, 1-amino-2-(3-hydroxyalk-1-ynyl)-9,10-anthraquinones undergo cyclization into 2-(1-hydroxyalkyl) naphthol 2,3-g]indole-6,11-diones. In contrast, 1-amino-2-(3-hydroxy-3-phenylpropynyl)-9,10-anthraquinone reacts with primary and secondary amines to give the corresponding 1-amino-2-(1-amino-2-benzoylvinyl)-9,10-anthraquinones, which undergo cyclization into 4-dialkylamino- or 4-alkylamino-2-phenylnaphtho[2,3-h]quinoline-7,12-diones. Heating of the starting phenylpropynol with Et3N causes its dehydrogenation and isomerization.