3,6-二乙氧基-2-甲基-2,5-二氢吡嗪 | 151369-36-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 中文名称: 3,6-二乙氧基-2-甲基-2,5-二氢吡嗪
• 英文名称: 3,6-Diethoxy-2,5-dihydro-2-methylpyrazine
• 英文别名: 3,6-Diethoxy-2-methyl-2,5-dihydropyrazine
• CAS: 151369-36-7
• 化学式: C₉H₁₆N₂O₂
• 分子量: 184.238
• InChiKey: MDUTVABPKZOLDL-UHFFFAOYSA-N

物化性质

• 沸点：
  252.1±33.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  43.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  邻氨基苯甲酸 、 3,6-二乙氧基-2-甲基-2,5-二氢吡嗪 反应 2.5h， 生成 1-methyl-2H-pyrazino[2,1-b]quinazoline-3,6-(1H,4H)-dione 、 4-methyl-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：

  triethyloxonium fluoroborate 、 3-methylpiperazine-2,5-dione 在 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 3,6-二乙氧基-2-甲基-2,5-二氢吡嗪
  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

• Groth, Ulrich; Huhn, Thomas; Porsch, Bettina, Liebigs Annalen der Chemie, 1993, # 7, p. 715 - 720
  作者：Groth, Ulrich、Huhn, Thomas、Porsch, Bettina、Schmeck, Carsten、Schoellkopf, Ulrich

  DOI：——

  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.