2-amino-4,6-bis(benzyloxy)-5-nitrosopyrimidine | 434937-46-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-amino-4,6-bis(benzyloxy)-5-nitrosopyrimidine
• 英文别名: 2-amino-4,6-bisbenzyloxy-5-nitrosopyrimidine；2-Amino-4,6-bis(benzyloxy)-5-nitrosopyrimidine；5-nitroso-4,6-bis(phenylmethoxy)pyrimidin-2-amine
• CAS: 434937-46-9
• 化学式: C₁₈H₁₆N₄O₃
• 分子量: 336.35
• InChiKey: XMUCICFYNVSCTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  99.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙烯胺 、 2-amino-4,6-bis(benzyloxy)-5-nitrosopyrimidine 以 乙醇 为溶剂， 生成 4-(allylamino)-2-amino-6-benzyloxy-5-nitrosopyrimidine
  参考文献：
  名称：

  4-(Allylamino)-2-amino-6-benzyloxy-5-nitrosopyrimidine from synchrotron data at 150 K: double chains built from N—H...N, N—H...O, N—H...π(arene) and aromatic π–π-stacking interactions

  摘要：

  In the title compound, C14H15N5O2, the intramolecular dimensions are consistent with a highly polarized electronic structure. The molecules are linked into chains by a combination of N-H...N, N-H...O and N-H...pi(arene) hydrogen bonds, and the chains are linked in pairs by aromatic pi-pi-stacking interactions.

  DOI：

  10.1107/s0108270102010387
• 作为产物：
  描述：

  苄基钠 在 亚硝酸异戊酯 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 生成 2-amino-4,6-bis(benzyloxy)-5-nitrosopyrimidine
  参考文献：
  名称：

  2-Amino-4,6-bis(benzyloxy)-5-nitrosopyrimidine: chains built from three-centre N—H...(N,O) and N—H...π(arene) hydrogen bonds

  摘要：

  The molecules of the title compound, C(18)H(16)N(4)O(3), exhibit a very polarized molecular-electronic structure. The molecules are linked into chains by a combination of an asymmetric three-centre N[bond]H...(N,O) hydrogen bond [H...N 2.19, H...O 2.54, N...N 3.041 (4) and N...O 2.977 (4) A, and N[bond]H...N 168, N[bond]H...O 112 and N...H...O 67 degrees ] and an N[bond]H...pi(arene) interaction [H...Cg 2.67 A, N...Cg 3.496 (4) A and N[bond]H...Cg 163 degrees; Cg is a benzyl ring centroid].

  DOI：

  10.1107/s0108270102008181

文献信息

• Alkoxy-5-nitrosopyrimidines: Useful Building Block for the Generation of Biologically Active Compounds
  作者：Antonio Marchal、Manuel Nogueras、Adolfo Sánchez、John N. Low、Lieve Naesens、Erik De Clercq、Manuel Melguizo

  DOI：10.1002/ejoc.201000195

  日期：——

  Several alkoxy-5-nitrosopyrimidines were synthesised and high regioselective and sequential nucleophilic aromatic substitution of methoxy groups in 2-amino-4,6-dimethoxy-5-nitrosopyrimidine was observed. The approach was applied to the synthesis of valuable polyfunctionalised aminopyrimidines capable of mimicking fused heterobicyclic derivatives of biological interest. In addition, new compounds were

  合成了几种烷氧基-5-亚硝基嘧啶，并观察到 ​​2-氨基-4,6-二甲氧基-5-亚硝基嘧啶中甲氧基的高区域选择性和顺序亲核芳香取代。该方法用于合成有价值的多官能化氨基嘧啶，其能够模拟具有生物学意义的稠合杂双环衍生物。此外，新化合物被评估为抗病毒药物，并证明了它们作为合成中间体的有用性。
• Novel Procedure for Selective C-Nitrosation of Aminopyrimidine Derivatives Under Neutral Conditions. Scope and Synthetic Applications
  作者：Antonio Marchal、Manuel Melguizo、Manuel Nogueras、Adolfo Sánchez、John N. Low

  DOI：10.1055/s-2002-19760

  日期：——

  A novel simple method, based on treatment with isoamyl nitrite (IAN) in DMSO without any added acid, to produce selective C(5)-nitrosation of aminopyrimidine derivatives is described. It proved to be suitable for a multigram scale and applicable to a larger range of pyrimidine derivatives, including amino-dialkoxypyrimidines, than the procedures previously known. Its scope is analyzed and some example on the usefulness of the newly prepared substances as intermediates in the synthesis of fused heterobicyclic derivatives of potential biological interest is presented.

  描述了一种新颖简单的方法，该方法基于在无任何添加酸的DMSO中用异戊醇硝酸酯（IAN）处理，实现对氨基嘧啶衍生物的选择性C(5)-亚硝化。该方法证明适合于多克级规模，并且适用于比之前已知程序更广泛的嘧啶衍生物，包括氨基-二烷氧基嘧啶。分析了其适用范围，并展示了一些新制备物作为潜在生物兴趣的融合杂环衍生物合成中的中间体的实用性示例。
• 4-(Allylamino)-2-amino-6-benzyloxy-5-nitrosopyrimidine from synchrotron data at 150 K: double chains built from N—H...N, N—H...O, N—H...π(arene) and aromatic π–π-stacking interactions
  作者：Elizabeth J. MacLean、John N. Low、Antonio Quesada、Manuel Melguizo、Manuel Nogueras、Christopher Glidewell

  DOI：10.1107/s0108270102010387

  日期：2002.7.15

  In the title compound, C14H15N5O2, the intramolecular dimensions are consistent with a highly polarized electronic structure. The molecules are linked into chains by a combination of N-H...N, N-H...O and N-H...pi(arene) hydrogen bonds, and the chains are linked in pairs by aromatic pi-pi-stacking interactions.
• 2-Amino-4,6-bis(benzyloxy)-5-nitrosopyrimidine: chains built from three-centre N—H...(N,O) and N—H...π(arene) hydrogen bonds
  作者：Antonio Quesada、John N. Low、Manuel Melguizo、Manuel Nogueras、Christopher Glidewell

  DOI：10.1107/s0108270102008181

  日期：2002.6.15

  The molecules of the title compound, C(18)H(16)N(4)O(3), exhibit a very polarized molecular-electronic structure. The molecules are linked into chains by a combination of an asymmetric three-centre N[bond]H...(N,O) hydrogen bond [H...N 2.19, H...O 2.54, N...N 3.041 (4) and N...O 2.977 (4) A, and N[bond]H...N 168, N[bond]H...O 112 and N...H...O 67 degrees ] and an N[bond]H...pi(arene) interaction [H...Cg 2.67 A, N...Cg 3.496 (4) A and N[bond]H...Cg 163 degrees; Cg is a benzyl ring centroid].