(+)-(1R,4S)-1-(2-bromomethylbenzyl)-3-ethoxy-4-methyl-1,4-dihydropyrazino[2,1-b]quinazolin-6-one | 870674-06-9

• 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: (+)-(1R,4S)-1-(2-bromomethylbenzyl)-3-ethoxy-4-methyl-1,4-dihydropyrazino[2,1-b]quinazolin-6-one
• CAS: 870674-06-9
• 化学式: C₂₂H₂₂BrN₃O₂
• 分子量: 440.34
• InChiKey: VRMZYWTWACNEGE-IFXJQAMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.58
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  56.48
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (+)-(1R,4S)-1-(2-bromomethylbenzyl)-3-ethoxy-4-methyl-1,4-dihydropyrazino[2,1-b]quinazolin-6-one 在 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以67%的产率得到(-)-(8S)-8-methyl-5H,8H-isoquinolino[2',3'-4,3]pyrazino[2,1-b]quinazoline-7,10-dione
  参考文献：
  名称：

  A new stereocontrolled approach to fused polycyclic compounds containing a diketopiperazine ring

  摘要：

  Representative (1S)- and (4S)-alkyl-1,4-dihydropyrazino[2,1-b]quinazoline-3,6-dione lactim ethers were regio- and diastereoselectively alkylated after metallation to give the corresponding 1,4-trans-isomers with retention of the stereocentres. The results were compared with the previously studied lactams. The (1R,4S)-dialkyl derivatives obtained by C(1)-alkyation with bifunctional reagents were lately cyclized to complex polycyclic compounds through a second N(2)-alkylation promoted by sodium iodide. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.034
• 作为产物：
  描述：

  (+)-(4S)-3-ethoxy-4-methyl-1,4-dihydropyrazino[2,1-b]quinazolin-6-one 、 1,2-二(溴甲基)苯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 16.17h， 以47%的产率得到(+)-(1R,4S)-1-(2-bromomethylbenzyl)-3-ethoxy-4-methyl-1,4-dihydropyrazino[2,1-b]quinazolin-6-one
  参考文献：
  名称：

  A new stereocontrolled approach to fused polycyclic compounds containing a diketopiperazine ring

  摘要：

  Representative (1S)- and (4S)-alkyl-1,4-dihydropyrazino[2,1-b]quinazoline-3,6-dione lactim ethers were regio- and diastereoselectively alkylated after metallation to give the corresponding 1,4-trans-isomers with retention of the stereocentres. The results were compared with the previously studied lactams. The (1R,4S)-dialkyl derivatives obtained by C(1)-alkyation with bifunctional reagents were lately cyclized to complex polycyclic compounds through a second N(2)-alkylation promoted by sodium iodide. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.034