(1S,4S)-2,4-dimethyl-1-hydroxy-2,4-dihydro-1H-pyrazino<2,1-b>quinazoline-3,6-dione | 221663-70-3

• 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)-2,4-dimethyl-1-hydroxy-2,4-dihydro-1H-pyrazino<2,1-b>quinazoline-3,6-dione
• 英文别名: (+)-(1S,4S)-2,4-dimethyl-1-hydroxy-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione；(1S,4S)-1-hydroxy-2,4-dimethyl-1,4-dihydropyrazino[2,1-b]quinazoline-3,6-dione
• CAS: 221663-70-3
• 化学式: C₁₃H₁₃N₃O₃
• 分子量: 259.265
• InChiKey: DTNYRHQVKJKMEH-CPFSXVBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  73.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,4S)-2,4-dimethyl-1-hydroxy-2,4-dihydro-1H-pyrazino<2,1-b>quinazoline-3,6-dione 在 pyridinium chlorochromate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (-)-(1R,4S)-1-hydroxy-2,4-dimethyl-1-phenyl-2,4-dihydro-(1H)-pyrazino[2,1-b]quinazoline-3,6-dione
  参考文献：
  名称：

  Cyclisation of (4S)-4-methyl-2-phenethyl-2,4-dihydro-(1H)-pyrazino[2,1-b]quinazoline-3,6-dione derivatives via N-acyliminium ions

  摘要：

  Enantiomerically pure 1-methylene and 1-oxo derivatives (compounds 4 and 10, respectively) of compounds 1 were obtained and studied as precursors of N-acyliminium ions. 1-Substituted-1-hydroxyderivatives, obtained by regioselective syn-addition of organometallics to compounds 10 gave the desired species under acid treatment while compounds 4 did not. -Phenethyl substituted N-acyliminium ions gave isoquino[1',2':3,4]pyrazino[2, l-b]quinazoline-8,11-diones through a Pictet-Spengler-type cyclisation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00492-x
• 作为产物：
  描述：

  (4S)-2,4-dimethyl-2,4-dihydro-(1H)-pyrazino<2,1-b>quinazoline-3,6-dione 在 氯化铵 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 14.0h， 生成 (1S,4S)-2,4-dimethyl-1-hydroxy-2,4-dihydro-1H-pyrazino<2,1-b>quinazoline-3,6-dione
  参考文献：
  名称：

  (4S)-2,4-Dimethyl-2,4-dihydro-3,6-dioxo-(1H)-pyrazino[2,1-b]quinazolyl tosylate as an electrophilic glycine template

  摘要：

  (4S)-2,4-二甲基-2,4-二氢(1H)-吡嗪并[2,1-b]喹唑啉-3,6-二酮被转化为顺式硫酸酯2，文中讨论了其作为电亲性甘氨酸模板的活性。发现该化合物不会直接发生S(N)2型的硫酸酯基取代反应。然而，其通过水解获得的1-羟基衍生物3（保留了立体化学），及其1-甲氧基衍生物4a则是电亲性甘氨酸模板。 © 1999 Elsevier Science Ltd. 保留所有权利。

  DOI：

  10.1016/s0040-4020(98)01188-0

文献信息

• (4S)-2,4-Dimethyl-2,4-dihydro-3,6-dioxo-(1H)-pyrazino[2,1-b]quinazolyl tosylate as an electrophilic glycine template
  作者：Sonsoles Martín-Santamaría、Modesta Espada、Carmen Avendaño

  DOI：10.1016/s0040-4020(98)01188-0

  日期：1999.2

  (4S)-2,4-Dimethyl-2,4-dihydro-(1H)-pyrazino[2,1- b]quinazoline-3,6-dione was converted into to the cis- tosylate 2, whose reactivity as an electrophilic glycine template is discussed. It was found that this compound does not give direct S(N)2-type displacement of the tosyloxy group. However, the 1-hydoxy derivative 3, obtained by hydrolysis of 2 with net retention of the stereochemistry, and its 1-methoxy derivative 4a are electrophilic glycine templates. (C) 1999 Elsevier Science Ltd. All rights reserved.

  (4S)-2,4-二甲基-2,4-二氢(1H)-吡嗪并[2,1-b]喹唑啉-3,6-二酮被转化为顺式硫酸酯2，文中讨论了其作为电亲性甘氨酸模板的活性。发现该化合物不会直接发生S(N)2型的硫酸酯基取代反应。然而，其通过水解获得的1-羟基衍生物3（保留了立体化学），及其1-甲氧基衍生物4a则是电亲性甘氨酸模板。 © 1999 Elsevier Science Ltd. 保留所有权利。
• Cyclisation of (4S)-4-methyl-2-phenethyl-2,4-dihydro-(1H)-pyrazino[2,1-b]quinazoline-3,6-dione derivatives via N-acyliminium ions
  作者：Marı́a Luisa Heredia、Elena de la Cuesta、Carmen Avendaño

  DOI：10.1016/s0957-4166(01)00492-x

  日期：2001.11

  Enantiomerically pure 1-methylene and 1-oxo derivatives (compounds 4 and 10, respectively) of compounds 1 were obtained and studied as precursors of N-acyliminium ions. 1-Substituted-1-hydroxyderivatives, obtained by regioselective syn-addition of organometallics to compounds 10 gave the desired species under acid treatment while compounds 4 did not. -Phenethyl substituted N-acyliminium ions gave isoquino[1',2':3,4]pyrazino[2, l-b]quinazoline-8,11-diones through a Pictet-Spengler-type cyclisation. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 1-Bromo-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones as α-bromoglycine templates
  作者：Marı́a Luisa Heredia、Marı́a Fernández、Elena de la Cuesta、Carmen Avendaño

  DOI：10.1016/s0957-4166(01)00067-2

  日期：2001.3

  The title compounds behaved as α-bromoglycine templates. Radical substitutions and SN1-type nucleophilic additions proceeded with retention of stereochemistry, while SN2-type displacements occurred with net inversion of configuration. A homocoupling product was obtained in attempting a Stille cross-coupling reaction.

  标题化合物表现为α-溴甘氨酸模板。自由基取代和S N 1型亲核加成继续保留立体化学，而S N 2型置换发生净构型倒置。在尝试进行Stille交叉偶联反应时获得了均偶联产物。