(4S)-2-(2'',4''-dimethoxybenzyl)-4-methyl-2,3,4,6-tetrahydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione | 204770-73-0

• 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-(2'',4''-dimethoxybenzyl)-4-methyl-2,3,4,6-tetrahydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione
• 英文别名: (4S)-2-[(2,4-dimethoxyphenyl)methyl]-4-methyl-1,4-dihydropyrazino[2,1-b]quinazoline-3,6-dione
• CAS: 204770-73-0
• 化学式: C₂₁H₂₁N₃O₄
• 分子量: 379.415
• InChiKey: CAAVUCDSMJLLQH-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S)-2-(2'',4''-dimethoxybenzyl)-4-methyl-2,3,4,6-tetrahydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione 在 苯甲醚 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 反应 7.83h， 生成 (+)-(1S,4S)-4-methyl-1-(p-methylbenzyl)-2,4-dihydro-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：

  N-(2,4-二甲氧基苄基)甘氨酸乙酯 在 palladium on activated charcoal 氢气 、 sodium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 25.0~140.0 ℃ 、241.32 kPa 条件下， 反应 28.5h， 生成 (4S)-2-(2'',4''-dimethoxybenzyl)-4-methyl-2,3,4,6-tetrahydro-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

文献信息

• Synthesis of a Seco Analogue of Ardeemin
  作者：Carmen Avendaño、Esmeralda Caballero、J. Carlos Menéndez

  DOI：10.3987/com-00-8942

  日期：——
• 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.