Methyl 9,10-dioxo-1-(3-phenoxyprop-1-ynyl)anthracene-2-carboxylate | 146135-84-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: Methyl 9,10-dioxo-1-(3-phenoxyprop-1-ynyl)anthracene-2-carboxylate
• CAS: 146135-84-4
• 化学式: C₂₅H₁₆O₅
• 分子量: 396.399
• InChiKey: MSSQGUCPDSSWTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 9,10-dioxo-1-(3-phenoxyprop-1-ynyl)anthracene-2-carboxylate 在 吡啶 、 copper(I) phenylacetylenide 、 氢氧化钾 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.58h， 生成 1-(2-phenoxyethylidene)naphtho[3,2-e][2]benzofuran-3,6,11-trione
  参考文献：
  名称：

  Cyclization of acetylenic derivatives of aromatic carboxylic acids

  摘要：

  The Cu(I)-catalyzed intramolecular cyclization of 1-phenylethynyl-and 1-hexyn-1-yl-anthraquinone-2-carboxylic acid is a 6-endo-dig-addition, whereas the reaction for 1-(3-phenoxypropyn-1-yl)anthraquinone-2-carboxylic acid proceeds in a directionally nonspecific way. It is shown that the cyclization of vicinal acetylenic derivatives of aromatic carboxylic acids leads to the formation of the more stable of the possible cyclic, structures.

  DOI：

  10.1007/bf00863591
• 作为产物：
  描述：

  1-iodoanthraquinone-2-carboxylic acid 在 吡啶 、 硫酸 作用下， 反应 40.0h， 生成 Methyl 9,10-dioxo-1-(3-phenoxyprop-1-ynyl)anthracene-2-carboxylate
  参考文献：
  名称：

  Cyclization of acetylenic derivatives of aromatic carboxylic acids

  摘要：

  The Cu(I)-catalyzed intramolecular cyclization of 1-phenylethynyl-and 1-hexyn-1-yl-anthraquinone-2-carboxylic acid is a 6-endo-dig-addition, whereas the reaction for 1-(3-phenoxypropyn-1-yl)anthraquinone-2-carboxylic acid proceeds in a directionally nonspecific way. It is shown that the cyclization of vicinal acetylenic derivatives of aromatic carboxylic acids leads to the formation of the more stable of the possible cyclic, structures.

  DOI：

  10.1007/bf00863591

文献信息

• Reactions of methyl 1-acetylenyl-9,10-anthraquinone-2-carboxylates with hydrazine
  作者：I. D. Ivanchikova、R. N. Myasnikova、M. S. Shvartsberg

  DOI：10.1007/bf02494509

  日期：1998.10

  Methyl 1-acetylenyl-9,10-anthraquinone-2-carboxylates react with NH2NH2 in ethanol at 80°C to give commensurable amounts of substituted 7H-dibenzo[de,h]quinolin-7-ones and 3,4-dihydro-3-aminonaphtho[2,3-f]isoquinoline-4,7,12-triones. The main, route of the reaction apparently includes nucleophilic addition of the reagent to the triple bond of the ester followed by intramolecular cyclization of the

  1-乙炔基-9,10-蒽醌-2-羧酸甲酯在 80°C 的乙醇中与 NH2NH2 反应，生成相当数量的取代 7H-二苯并[de,h]quinolin-7-ones 和 3,4-dihydro-3 -aminonaphtho[2,3-f]isoquinoline-4,7,12-triones。反应的主要途径显然包括将试剂亲核加成到酯的三键上，然后加合物与所涉及的羰基或甲氧基羰基进行分子内环化。