6-amino-5-(1-(4-(dimethylamino)phenyl)-2-nitroethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione | 95834-25-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 6-amino-5-(1-(4-(dimethylamino)phenyl)-2-nitroethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione
• 英文别名: 6-Amino-5-[1-[4-(dimethylamino)phenyl]-2-nitroethyl]-1,3-dimethylpyrimidine-2,4-dione
• CAS: 95834-25-6
• 化学式: C₁₆H₂₁N₅O₄
• 分子量: 347.374
• InChiKey: JUOSPQSAJWBDQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-amino-5-(1-(4-(dimethylamino)phenyl)-2-nitroethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 在 sodium dithionite 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以46%的产率得到5-(4-(dimethylamino)phenyl)-1,3-dimethyl-1H-pyrrolo[2,3-d]pyrimidine-2,4(3H,7H)-dione
  参考文献：
  名称：

  A one pot, two-step synthesis of 5-arylpyrrolo[2,3- d ]pyrimidines and screening of their preliminary antibacterial properties

  摘要：

  A one pot two step methodology for the synthesis of ten derivatives of 5-arylpyrrolo[2,3-d]pyrimidine has been reported. The methodology exploits the strong reducing nature of alkaline Na2S2O4 solution coupled with favorability of Michael type addition reaction in alkaline medium. The methodology demands attraction as it is non-catalytic, quite general for wide range of nitrostyrenes and possesses comprehensive advantages over most of the earlier methods in terms of reaction time as well as yield. The methodology enjoys additional advantage of utilizing cheaper and easily available chemicals as reagent for the purpose. Some of the synthesized compounds are found to possess remarkable activity against some of the tested bacterial strains. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.12.047
• 作为产物：
  描述：

  1,3-二甲基-6-氨基脲嘧啶 、 1-nitro-2-(4'-dimethylaminophenyl)ethene 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以54%的产率得到6-amino-5-(1-(4-(dimethylamino)phenyl)-2-nitroethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  A one pot, two-step synthesis of 5-arylpyrrolo[2,3- d ]pyrimidines and screening of their preliminary antibacterial properties

  摘要：

  A one pot two step methodology for the synthesis of ten derivatives of 5-arylpyrrolo[2,3-d]pyrimidine has been reported. The methodology exploits the strong reducing nature of alkaline Na2S2O4 solution coupled with favorability of Michael type addition reaction in alkaline medium. The methodology demands attraction as it is non-catalytic, quite general for wide range of nitrostyrenes and possesses comprehensive advantages over most of the earlier methods in terms of reaction time as well as yield. The methodology enjoys additional advantage of utilizing cheaper and easily available chemicals as reagent for the purpose. Some of the synthesized compounds are found to possess remarkable activity against some of the tested bacterial strains. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.12.047

文献信息

• Studies on pyrimidine derivatives. Michael addition of β-nitrostyrenes to substituted 6-aminouracils
  作者：A. Siva Prasad、J. S. Sandhu、J. N. Baruah

  DOI：10.1002/jhet.5570210617

  日期：1984.11

  A series of 5-(2-nitro-l-phenyl)ethyluracils were obtained when β-nitrostyrenes were reacted with 1,3-di-methyl-6-substituted uracil derivatives, instead of cyclic compounds. The structures of the compounds 5, 6, and 7 were proved by spectroscopic methods and their mass fragmentation patterns are discussed.

  当β-硝基苯乙烯与1,3-二甲基-6-取代的尿嘧啶衍生物而不是环状化合物反应时，获得了一系列的5-（2-硝基-1-苯基）乙基尿嘧啶。通过光谱方法证明了化合物5、6和7的结构，并讨论了其质量碎片模式。
• PRASAD, A. S.;SANDHU, J. S.;BARUAH, J. N., J. HETEROCYCL. CHEM., 1984, 21, N 6, 1657-1659
  作者：PRASAD, A. S.、SANDHU, J. S.、BARUAH, J. N.

  DOI：——

  日期：——
• A one pot, two-step synthesis of 5-arylpyrrolo[2,3- d ]pyrimidines and screening of their preliminary antibacterial properties
  作者：Lakhinath Saikia、P. Roudragouda、Ashim J. Thakur

  DOI：10.1016/j.bmcl.2015.12.047

  日期：2016.2

  A one pot two step methodology for the synthesis of ten derivatives of 5-arylpyrrolo[2,3-d]pyrimidine has been reported. The methodology exploits the strong reducing nature of alkaline Na2S2O4 solution coupled with favorability of Michael type addition reaction in alkaline medium. The methodology demands attraction as it is non-catalytic, quite general for wide range of nitrostyrenes and possesses comprehensive advantages over most of the earlier methods in terms of reaction time as well as yield. The methodology enjoys additional advantage of utilizing cheaper and easily available chemicals as reagent for the purpose. Some of the synthesized compounds are found to possess remarkable activity against some of the tested bacterial strains. (C) 2015 Elsevier Ltd. All rights reserved.