(-)-(1R,4S)-1-hydroxy-4-methyl-2-phenethyl-1-phenyl-2,4-dihydro-(1H)-pyrazino[2,1-b]quinazoline-3,6-dione | 420110-14-1

• 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: (-)-(1R,4S)-1-hydroxy-4-methyl-2-phenethyl-1-phenyl-2,4-dihydro-(1H)-pyrazino[2,1-b]quinazoline-3,6-dione
• CAS: 420110-14-1
• 化学式: C₂₆H₂₃N₃O₃
• 分子量: 425.487
• InChiKey: SMGRLLYKJXZETF-HFJWLAOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  75.43
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (-)-(1R,4S)-1-hydroxy-4-methyl-2-phenethyl-1-phenyl-2,4-dihydro-(1H)-pyrazino[2,1-b]quinazoline-3,6-dione 在 硫酸 作用下， 以54%的产率得到(-)-(9S,16bR)-9-methyl-16b-phenyl-5,6,9,16b-tetrahydroisoquino[1',2':3,4]pyrazino[2,1-b]quinazoline-8,11-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)-4-methyl-2-phenethyl-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione 在 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (-)-(1R,4S)-1-hydroxy-4-methyl-2-phenethyl-1-phenyl-2,4-dihydro-(1H)-pyrazino[2,1-b]quinazoline-3,6-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