diisopropyl 4,6-diamino-1,3,5-triazine-2-yl phosphonate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: diisopropyl 4,6-diamino-1,3,5-triazine-2-yl phosphonate
• 英文别名: diisopropyl 4,6-diamino-1,3,5-triazin-2-ylphosphonate；6-Di(propan-2-yloxy)phosphoryl-1,3,5-triazine-2,4-diamine
• 化学式: C₉H₁₈N₅O₃P
• 分子量: 275.247
• InChiKey: KWWRBYNOBJASQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  diisopropyl 4,6-diamino-1,3,5-triazine-2-yl phosphonate 在 三甲基溴硅烷 作用下， 以 乙腈 为溶剂， 以80%的产率得到4,6-diamino-1,3,5-triazin-2-ylphosphonic acid
  参考文献：
  名称：

  An efficient microwave-assisted synthesis and biological properties of polysubstituted pyrimidinyl- and 1,3,5-triazinylphosphonic acids

  摘要：

  Polysubstituted pyrimidinylphosphonic and 1,3,5-triazinylphosphonic acids with potential biological properties were prepared in high yields by the microwave-assisted Michaelis Arbuzov reaction of trialkyl phosphite with the corresponding halopyrimidines and halo-1,3,5-triazines, respectively, followed by the standard deprotection of the phosphonate group using TMSBr in acetonitrile. 4,6-Diamino-5chloropyrimidin-2-ylphosphonic acid (7a) was found to exhibit a weak to moderate anti-influenza activity (28-50 uM) and may represent a novel hit for further SAR studies and antiviral improvement. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.040
• 作为产物：
  描述：

  亚磷酸二异丙酯 在 sodium isopropylate 、 sodium hydride 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 5.0h， 生成 diisopropyl 4,6-diamino-1,3,5-triazine-2-yl phosphonate
  参考文献：
  名称：

  N-氰基-膦酰基/S-甲基硫代碳酸酯：用于合成杂环膦酸酯的简便、有用的试剂

  摘要：

  N-氰基亚胺基-(O,O-二烷基)膦酰基/S-甲基硫代碳酸酯 2 被合成为方便、有用的合成子，用于制备 1,3,5-三嗪-、1,2,4-三唑-和 1,2 ,4-恶二唑膦酸酯通过与各种亲核试剂的环化反应生成。此外，当2a用邻苯二胺处理时，通过加消反应得到苯并咪唑-2-基膦酸酯。

  DOI：

  10.1081/scc-100108232

文献信息

• PHOSPHORUS-CONTAINING TRIAZINE COMPOUNDS AND THEIR USE
  申请人：COURTAULDS PLC

  公开号：EP0617717A1

  公开（公告）日：1994-10-05
• US5534573A
  申请人：——

  公开号：US5534573A

  公开（公告）日：1996-07-09
• [EN] PHOSPHORUS-CONTAINING TRIAZINE COMPOUNDS AND THEIR USE
  申请人：——

  公开号：WO1993012173A2

  公开（公告）日：1993-06-24

  [EN] Triazine compounds useful as flame retardants have the formula (I) where Am represents an amino group, Pp represents a phosphonic group and Z represents an amino group or a phosphonic group, or are polymers comprising repeating units of formula (II), where (a) is a diamine residue. The triazine compounds are used as flame retardants in plastic materials, particularly polyurethane foam or artificial fibres, or in intumescent fire protection compositions.
  [FR] Les composés de triazine utilisés comme retardateurs de flamme répondent à la formule (I) où Am représente un groupe amino, Pp représente un groupe phosphonique et Z représente un groupe amino ou un groupe phosphonique, ou sont des polymères contenant des motifs répétitifs répondant à la formule (II) où (a) est un reste diamine. Les composés de triazine sont utilisés comme retardateurs de flamme dans les matières plastiques, en particulier la mousse de polyuréthane ou les fibres artificielles, on encore dans des compositions intumescentes de protection contre les incendies.
• An efficient microwave-assisted synthesis and biological properties of polysubstituted pyrimidinyl- and 1,3,5-triazinylphosphonic acids
  作者：Petr Jansa、Ondřej Hradil、Ondřej Baszczyňski、Martin Dračínský、Blanka Klepetářová、Antonín Holý、Jan Balzarini、Zlatko Janeba

  DOI：10.1016/j.tet.2011.11.040

  日期：2012.1

  Polysubstituted pyrimidinylphosphonic and 1,3,5-triazinylphosphonic acids with potential biological properties were prepared in high yields by the microwave-assisted Michaelis Arbuzov reaction of trialkyl phosphite with the corresponding halopyrimidines and halo-1,3,5-triazines, respectively, followed by the standard deprotection of the phosphonate group using TMSBr in acetonitrile. 4,6-Diamino-5chloropyrimidin-2-ylphosphonic acid (7a) was found to exhibit a weak to moderate anti-influenza activity (28-50 uM) and may represent a novel hit for further SAR studies and antiviral improvement. (C) 2011 Elsevier Ltd. All rights reserved.
• <i>N</i>-CYANOIMIDO-PHOSPHONYL/<i>S</i>-METHYL THIOCARBONATES: FACILE, USEFUL REAGENTS FOR THE SYNTHESES OF HETEROCYCLIC PHOSPHONATES
  作者：Fangzhong Hu、Huazheng Yang

  DOI：10.1081/scc-100108232

  日期：2001.1.1

  N-Cyanoimido-(O,O-dialkyl) phosphonyl/S-methyl thiocarbonates 2 were synthesized as facile, useful synthons for preparation of 1,3,5-triazine-, 1,2,4-triazole-, and 1,2,4-oxadiazole-phosphonates through cyclization reaction with various binucleophilic reagents. In addition, when 2a was treated with o-phenylenediamine, benzimidazole-2-yl phosphonate was obtained through addition–elimination reaction.

  N-氰基亚胺基-(O,O-二烷基)膦酰基/S-甲基硫代碳酸酯 2 被合成为方便、有用的合成子，用于制备 1,3,5-三嗪-、1,2,4-三唑-和 1,2 ,4-恶二唑膦酸酯通过与各种亲核试剂的环化反应生成。此外，当2a用邻苯二胺处理时，通过加消反应得到苯并咪唑-2-基膦酸酯。