(4S)-2,4-dihydro-2,4-dimethylpyrazino[2,1-b]quinazoline-1,3,6-trione | 204513-01-9

• 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: (4S)-2,4-dihydro-2,4-dimethylpyrazino[2,1-b]quinazoline-1,3,6-trione
• 英文别名: (4S)-2,4-dimethyl-4H-pyrazino[2,1-b]quinazoline-1,3,6-trione
• CAS: 204513-01-9
• 化学式: C₁₃H₁₁N₃O₃
• 分子量: 257.249
• InChiKey: CCCZZBUXKKYLHW-ZETCQYMHSA-N

物化性质

• 熔点：
  166-168 °C
• 沸点：
  411.726±28.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.489±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  70
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S)-2,4-dihydro-2,4-dimethylpyrazino[2,1-b]quinazoline-1,3,6-trione 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 生成 (4S)-(-)-2,4-dimethyl-1-methylidene-1,2-dihydro-6H-pyrazino[2,1-b]quinazoline-3(4H),6-dione
  参考文献：
  名称：

  Cyclisation of (4S)-4-methyl-2-phenethyl-2,4-dihydro-(1H)-pyrazino[2,1-b]quinazoline-3,6-dione derivatives via N-acyliminium ions

  摘要：

  Enantiomerically pure 1-methylene and 1-oxo derivatives (compounds 4 and 10, respectively) of compounds 1 were obtained and studied as precursors of N-acyliminium ions. 1-Substituted-1-hydroxyderivatives, obtained by regioselective syn-addition of organometallics to compounds 10 gave the desired species under acid treatment while compounds 4 did not. -Phenethyl substituted N-acyliminium ions gave isoquino[1',2':3,4]pyrazino[2, l-b]quinazoline-8,11-diones through a Pictet-Spengler-type cyclisation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00492-x
• 作为产物：
  描述：

  (4S)-2,4-dimethyl-2,4-dihydro-(1H)-pyrazino<2,1-b>quinazoline-3,6-dione 在 air 、 sodium acetate 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 15.5h， 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

文献信息

• Cledera, Pilar; Villacampa, Mercedes; Avendano, Carmen, ARKIVOC, 2011, vol. 2011, # 3, p. 72 - 98
  作者：Cledera, Pilar、Villacampa, Mercedes、Avendano, Carmen、Menendez, J. Carlos

  DOI：——

  日期：——
• Vilsmeier and Mannich reactions on (4S)-N2-substituted 4-methyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones
  作者：María Fernandez、María L. Heredia、Elena de la Cuesta、Carmen Avendaño

  DOI：10.1016/s0040-4020(98)83013-5

  日期：1998.3

  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.
• Cyclisation of (4S)-4-methyl-2-phenethyl-2,4-dihydro-(1H)-pyrazino[2,1-b]quinazoline-3,6-dione derivatives via N-acyliminium ions
  作者：Marı́a Luisa Heredia、Elena de la Cuesta、Carmen Avendaño

  DOI：10.1016/s0957-4166(01)00492-x

  日期：2001.11

  Enantiomerically pure 1-methylene and 1-oxo derivatives (compounds 4 and 10, respectively) of compounds 1 were obtained and studied as precursors of N-acyliminium ions. 1-Substituted-1-hydroxyderivatives, obtained by regioselective syn-addition of organometallics to compounds 10 gave the desired species under acid treatment while compounds 4 did not. -Phenethyl substituted N-acyliminium ions gave isoquino[1',2':3,4]pyrazino[2, l-b]quinazoline-8,11-diones through a Pictet-Spengler-type cyclisation. (C) 2001 Elsevier Science Ltd. All rights reserved.