(4S)-(-)-2,4-dimethyl-1-methylidene-1,2-dihydro-6H-pyrazino[2,1-b]quinazoline-3(4H),6-dione | 204513-08-6

• 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-dimethyl-1-methylidene-1,2-dihydro-6H-pyrazino[2,1-b]quinazoline-3(4H),6-dione
• 英文别名: (4S)-2,4-dimethyl-1-methylidene-4H-pyrazino[2,1-b]quinazoline-3,6-dione
• CAS: 204513-08-6
• 化学式: C₁₄H₁₃N₃O₂
• 分子量: 255.276
• InChiKey: MQSZCMWWLFKCJC-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  53
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  sodium thiophenolate 、 (4S)-(-)-2,4-dimethyl-1-methylidene-1,2-dihydro-6H-pyrazino[2,1-b]quinazoline-3(4H),6-dione 以 四氢呋喃 为溶剂， 以52%的产率得到
  参考文献：
  名称：

  （4 S）-1-亚烷基-2,4-二氢-1 H-吡嗪并[2,1 - b ]喹唑啉-3,6-二酮的亲核加成

  摘要：

  标题化合物为双氢氨基酸模板的研究表明，它们在铜（I）催化下对胺或格氏试剂缺乏反应性，但硫醇盐或稳定的碳负离子有效地加到了环外双键上。在C（3）-位发生有机金属试剂的区域和非对映选择性加成，在1-亚甲基衍生物中，这些反应之后是中间氧阴离子的重排，从而得到吡啶并[2,1- b ]喹唑啉。

  DOI：

  10.1016/s0040-4020(01)00046-1
• 作为产物：
  描述：

  (1S,4S)-2,4-dimethyl-1-hydroxy-2,4-dihydro-1H-pyrazino<2,1-b>quinazoline-3,6-dione 在 对甲苯磺酸 、 pyridinium chlorochromate 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

文献信息

• 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.