(S)-1-[1-Methoxy-meth-(Z)-ylidene]-2,4-dimethyl-1,2-dihydro-2,4a,9-triaza-anthracene-3,10-dione | 204513-05-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (S)-1-[1-Methoxy-meth-(Z)-ylidene]-2,4-dimethyl-1,2-dihydro-2,4a,9-triaza-anthracene-3,10-dione
• CAS: 204513-05-3
• 化学式: C₁₅H₁₅N₃O₃
• 分子量: 285.302
• InChiKey: WKVWCXZVTQGCGZ-RILYUOAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  64.43
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-1-[1-Methoxy-meth-(Z)-ylidene]-2,4-dimethyl-1,2-dihydro-2,4a,9-triaza-anthracene-3,10-dione 在 air 作用下， 生成 (4S)-2,4-dihydro-2,4-dimethylpyrazino[2,1-b]quinazoline-1,3,6-trione
  参考文献：
  名称：

  Vilsmeier and Mannich reactions on (4S)-N2-substituted 4-methyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones

  摘要：

  The enamine character of the CH2-C(11a)=N(11) fragment in the title compounds was studied. Compounds 1 gave 1-dimethylaminomethylene products 5 after Vilsmeier reaction. The l-formyl derivatives, obtained by alkaline hydrolysis of 5, were isolated as enol tautomers and were very unstable in acid media. On the other hand, acid-promoted elimination of dimethylamine from the Mannich reaction products 7 gave I-methylene derivatives 8, which showed an interesting reactivity. Thus, 8a dimerized in acid to the ethylidene derivative 9a. 1,4-Dialkyl-compounds 7 and 9a showed a 1,4-syn-stereochemistry. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)83013-5
• 作为产物：
  描述：

  (4S)-2,4-dimethyl-2,4-dihydro-(1H)-pyrazino<2,1-b>quinazoline-3,6-dione 在 sodium acetate 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 15.5h， 生成 (S)-1-[1-Methoxy-meth-(Z)-ylidene]-2,4-dimethyl-1,2-dihydro-2,4a,9-triaza-anthracene-3,10-dione
  参考文献：
  名称：

  Vilsmeier and Mannich reactions on (4S)-N2-substituted 4-methyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones

  摘要：

  The enamine character of the CH2-C(11a)=N(11) fragment in the title compounds was studied. Compounds 1 gave 1-dimethylaminomethylene products 5 after Vilsmeier reaction. The l-formyl derivatives, obtained by alkaline hydrolysis of 5, were isolated as enol tautomers and were very unstable in acid media. On the other hand, acid-promoted elimination of dimethylamine from the Mannich reaction products 7 gave I-methylene derivatives 8, which showed an interesting reactivity. Thus, 8a dimerized in acid to the ethylidene derivative 9a. 1,4-Dialkyl-compounds 7 and 9a showed a 1,4-syn-stereochemistry. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)83013-5