(1S,4S)-2-benzyl-4-methyl-1-[(4-methylphenyl)methyl]-1,4-dihydropyrazino[2,1-b]quinazoline-3,6-dione

• 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: (1S,4S)-2-benzyl-4-methyl-1-[(4-methylphenyl)methyl]-1,4-dihydropyrazino[2,1-b]quinazoline-3,6-dione
• 化学式: C₂₇H₂₅N₃O₂
• 分子量: 423.514
• InChiKey: JUTDMVLKVHFYAG-CYFREDJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  4-甲基苄溴 、 (1S,4S)-2-benzyl-4-methyl-1-[(4-methylphenyl)methyl]-1,4-dihydropyrazino[2,1-b]quinazoline-3,6-dione 在 lithium hexamethyldisilazane 作用下， 生成 (1S,4R)-2-benzyl-4-methyl-1,4-bis[(4-methylphenyl)methyl]-1H-pyrazino[2,1-b]quinazoline-3,6-dione
  参考文献：
  名称：

  New findings in the alkylation and N-deprotection of (4S)-4-methyl-2-benzyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones

  摘要：

  Alkyl halides behave differently to benzyl halides in C-1 alkylation of the title compounds. The syn and anti 1,4-disubstituted diastereomers thus obtained show different regioselectivity by further alkylation leading to the 1,4,4- and 1,1,4-trisubstituted compounds, respectively. Alkylation is always directed anti with respect to the bulkier substituent at C-1 or C-4. Debenzylation attempts on 2-benzyl-derivatives 1b by treatment with HCOOH and C/Pd or H-2/C-Pd/MeOH/H+ led to C-1 oxidised or 7,8,9,10-tetrahydro-derivatives. Deprotection of 2-p-methoxybenzyl- and 2-(2,4-dimethoxybenzyl)-derivatives with CAN and with TFA/anisole, respectively, was successful, but in the latter case epimerization at C-1 occurred. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00629-0
• 作为产物：
  描述：

  2,5-哌嗪二酮,3-甲基-1-(苯基甲基)-,(3S)- 在 triethyloxonium fluoroborate 、 sodium carbonate 、 lithium hexamethyldisilazane 作用下， 反应 3.75h， 生成 (1S,4S)-2-benzyl-4-methyl-1-[(4-methylphenyl)methyl]-1,4-dihydropyrazino[2,1-b]quinazoline-3,6-dione
  参考文献：
  名称：

  Regio- and Diastereoselective Alkylation of 2-Substituted 2,4-Dihydro-1H- pyrazino[2,1-b]quinazoline-3,6-diones

  摘要：

  DOI：

  10.1021/jo970037a

文献信息

• New findings in the alkylation and N-deprotection of (4S)-4-methyl-2-benzyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones
  作者：Félix L. Buenadicha、M.Teresa Bartolomé、M.Jesús Aguirre、Carmen Avendaño、Mónica Söllhuber

  DOI：10.1016/s0957-4166(97)00629-0

  日期：1998.2

  Alkyl halides behave differently to benzyl halides in C-1 alkylation of the title compounds. The syn and anti 1,4-disubstituted diastereomers thus obtained show different regioselectivity by further alkylation leading to the 1,4,4- and 1,1,4-trisubstituted compounds, respectively. Alkylation is always directed anti with respect to the bulkier substituent at C-1 or C-4. Debenzylation attempts on 2-benzyl-derivatives 1b by treatment with HCOOH and C/Pd or H-2/C-Pd/MeOH/H+ led to C-1 oxidised or 7,8,9,10-tetrahydro-derivatives. Deprotection of 2-p-methoxybenzyl- and 2-(2,4-dimethoxybenzyl)-derivatives with CAN and with TFA/anisole, respectively, was successful, but in the latter case epimerization at C-1 occurred. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Regio- and Diastereoselective Alkylation of 2-Substituted 2,4-Dihydro-1<b><i>H</i></b>- pyrazino[2,1-<b><i>b</i></b>]quinazoline-3,6-diones
  作者：Sonsoles Martín-Santamaría、Félix L. Buenadicha、Modesta Espada、Mónica Söllhuber、Carmen Avendaño

  DOI：10.1021/jo970037a

  日期：1997.9.1