(4S)-2-acetyl-4-methyl-1,2,3,4-tetrahydro-5H-pyrazino[2.1-b]quinazoline-3,6-dione | 264236-30-8

• 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-acetyl-4-methyl-1,2,3,4-tetrahydro-5H-pyrazino[2.1-b]quinazoline-3,6-dione
• 英文别名: (4S)-2-acetyl-1,2,3,4-tetrahydro-4-methyl-5H-pyrazino[2,1-b]quinazoline-3,6-dione；(4S)-2-acetyl-4-methyl-1,4-dihydropyrazino[2,1-b]quinazoline-3,6-dione
• CAS: 264236-30-8
• 化学式: C₁₄H₁₃N₃O₃
• 分子量: 271.276
• InChiKey: PDAFXRVKPPFYKG-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  70
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S)-2-acetyl-4-methyl-1,2,3,4-tetrahydro-5H-pyrazino[2.1-b]quinazoline-3,6-dione 在 一水合肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以66%的产率得到(4S)-4-methyl-1,2,3,4-tetrahydro-5H-pyrazino[2,1-b]quinazoline-3,6-dione
  参考文献：
  名称：

  A New Route toward 4-Substituted Pyrazino[2,1-b]quinazoline-3,6-dione Systems. Total Synthesis of Glyantrypine

  摘要：

  Treatment of sodium N-(o-azidobenzoyl)aminoacylglycinates 8 with acetic anhydride afforded 1-acetyl-4-(o-azidobenzoyl)-2,5-piperazinediones 7, with complete retention of the stereochemistry. The intramolecular aza Wittig reactions of compounds 7 in the presence of tributylphosphine followed by deacetylation gave 1,2-unsubstituted pyrazino[2,1-b]quinazoline-3,6-diones 1. This route was adapted to the synthesis of both enantiomers of the alkaloid glyantrypine.

  DOI：

  10.1021/jo991626e
• 作为产物：
  描述：

  ethyl N-(benzyloxycarbonyl)-L-alanylglycinate 在 palladium on activated charcoal 4-二甲氨基吡啶 、 sodium hydroxide 、 三丁基膦 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 43.0h， 生成 (4S)-2-acetyl-4-methyl-1,2,3,4-tetrahydro-5H-pyrazino[2.1-b]quinazoline-3,6-dione
  参考文献：
  名称：

  A New Route toward 4-Substituted Pyrazino[2,1-b]quinazoline-3,6-dione Systems. Total Synthesis of Glyantrypine

  摘要：

  Treatment of sodium N-(o-azidobenzoyl)aminoacylglycinates 8 with acetic anhydride afforded 1-acetyl-4-(o-azidobenzoyl)-2,5-piperazinediones 7, with complete retention of the stereochemistry. The intramolecular aza Wittig reactions of compounds 7 in the presence of tributylphosphine followed by deacetylation gave 1,2-unsubstituted pyrazino[2,1-b]quinazoline-3,6-diones 1. This route was adapted to the synthesis of both enantiomers of the alkaloid glyantrypine.

  DOI：

  10.1021/jo991626e

文献信息

• Cledera, Pilar; Villacampa, Mercedes; Avendano, Carmen, ARKIVOC, 2011, vol. 2011, # 3, p. 72 - 98
  作者：Cledera, Pilar、Villacampa, Mercedes、Avendano, Carmen、Menendez, J. Carlos

  DOI：——

  日期：——
• A New Route toward 4-Substituted Pyrazino[2,1-<i>b</i>]quinazoline-3,6-dione Systems. Total Synthesis of Glyantrypine
  作者：Pilar Cledera、Carmen Avendaño、J. Carlos Menéndez

  DOI：10.1021/jo991626e

  日期：2000.3.1

  Treatment of sodium N-(o-azidobenzoyl)aminoacylglycinates 8 with acetic anhydride afforded 1-acetyl-4-(o-azidobenzoyl)-2,5-piperazinediones 7, with complete retention of the stereochemistry. The intramolecular aza Wittig reactions of compounds 7 in the presence of tributylphosphine followed by deacetylation gave 1,2-unsubstituted pyrazino[2,1-b]quinazoline-3,6-diones 1. This route was adapted to the synthesis of both enantiomers of the alkaloid glyantrypine.