ethyl (1-amino-9,10-anthraquinon-2-yl)propynoate | 192703-71-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: ethyl (1-amino-9,10-anthraquinon-2-yl)propynoate
• 英文别名: (1-aminoanthraquinon-2-yl)propiolic acid ethyl ester；ethyl 3-(1-amino-9,10-dioxoanthracen-2-yl)prop-2-ynoate
• CAS: 192703-71-2
• 化学式: C₁₉H₁₃NO₄
• 分子量: 319.317
• InChiKey: HVGJCVUWLLALLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  86.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (1-amino-9,10-anthraquinon-2-yl)propynoate 在 三氯氧磷 作用下， 以 1,4-二氧六环 为溶剂， 反应 9.5h， 生成 4-butylamino-2-chloronaphtho<2,3-h>quinoline-7,12-dion
  参考文献：
  名称：

  Functionalized naphthol[2,3-h] quinoline-7,12-diones

  摘要：

  The addition of secondary and primary amines to ethyl (1-amino-9,10-anthraquinon-2-yl)propynoate affords an easily separable mixture of the corresponding ethyl 3-dialkylamino- or 3-alkylamino-3-(1-amino-9, 10-anthraquinon-2-yl)acrylate and 3-dialkylamino- or 3-alkylaminonaphtho[2,3-h]quinoline-2(1H),7,12-trione (in similar to 4: 1 ratio). Intramolecular cyclization of the resulting substituted ethyl acrylates results in the formation of 4-dialkylamino- or 4-alkylamino-2-chlorinated pyridine rings. Subsequent nucleophilic substitution of the chlorine atom gives 2-functionalized 4-dialkylamino- or 4-alkylaminonaphtho[2,3-h]quinoline-7,12-diones.

  DOI：

  10.1007/bf02494292
• 作为产物：
  描述：

  1-amino-2-iodo-9,10-anthraquinone 、 丙炔酸乙酯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.08h， 以74.4%的产率得到ethyl (1-amino-9,10-anthraquinon-2-yl)propynoate
  参考文献：
  名称：

  Functionalized naphthol[2,3-h] quinoline-7,12-diones

  摘要：

  The addition of secondary and primary amines to ethyl (1-amino-9,10-anthraquinon-2-yl)propynoate affords an easily separable mixture of the corresponding ethyl 3-dialkylamino- or 3-alkylamino-3-(1-amino-9, 10-anthraquinon-2-yl)acrylate and 3-dialkylamino- or 3-alkylaminonaphtho[2,3-h]quinoline-2(1H),7,12-trione (in similar to 4: 1 ratio). Intramolecular cyclization of the resulting substituted ethyl acrylates results in the formation of 4-dialkylamino- or 4-alkylamino-2-chlorinated pyridine rings. Subsequent nucleophilic substitution of the chlorine atom gives 2-functionalized 4-dialkylamino- or 4-alkylaminonaphtho[2,3-h]quinoline-7,12-diones.

  DOI：

  10.1007/bf02494292

文献信息

• New method for the synthesis of thieno[2,3-d]pyrimidines
  作者：O. B. Ryabova、M. I. Evstratova、V. A. Makarov、V. A. Tafeenko、V. G. Granik

  DOI：10.1007/s10593-005-0082-y

  日期：2004.10
• Functionalized naphthol[2,3-h] quinoline-7,12-diones
  作者：I. I. Barabanov、L. G. Fedenok、M. S. Shvartsberg

  DOI：10.1007/bf02494292

  日期：1998.11

  The addition of secondary and primary amines to ethyl (1-amino-9,10-anthraquinon-2-yl)propynoate affords an easily separable mixture of the corresponding ethyl 3-dialkylamino- or 3-alkylamino-3-(1-amino-9, 10-anthraquinon-2-yl)acrylate and 3-dialkylamino- or 3-alkylaminonaphtho[2,3-h]quinoline-2(1H),7,12-trione (in similar to 4: 1 ratio). Intramolecular cyclization of the resulting substituted ethyl acrylates results in the formation of 4-dialkylamino- or 4-alkylamino-2-chlorinated pyridine rings. Subsequent nucleophilic substitution of the chlorine atom gives 2-functionalized 4-dialkylamino- or 4-alkylaminonaphtho[2,3-h]quinoline-7,12-diones.