6-amino-1,3-dimethyl-5-(2-nitro-1-phenylethyl)pyrimidine-2,4(1H,3H)-dione | 95834-23-4

• 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: 6-amino-1,3-dimethyl-5-(2-nitro-1-phenylethyl)pyrimidine-2,4(1H,3H)-dione
• 英文别名: 1,3-Dimethyl-5-(1'-phenyl-2'-nitroethyl)-6-aminouracil；6-Amino-1,4(1H,3H)-pyrimidinedione；6-amino-1,3-dimethyl-5-(2-nitro-1-phenylethyl)pyrimidine-2,4-dione
• CAS: 95834-23-4
• 化学式: C₁₄H₁₆N₄O₄
• 分子量: 304.305
• InChiKey: DPHNQIQOHLNRDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-amino-1,3-dimethyl-5-(2-nitro-1-phenylethyl)pyrimidine-2,4(1H,3H)-dione 在 sodium dithionite 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 1.0h， 以92%的产率得到1,3-dimethyl-5-phenyl-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：

  反式硝基苯乙烯 、 6-氨基二氢-1,3-二甲基-2,4(1H,3H) -嘧啶二酮 在 2Zn⁽²⁺⁾*2NO₃^(1-)*2C₃H₇NO*2Y⁽³⁺⁾*4C₁₄H₁₁NO₃^(2-) 作用下， 以 乙醇 、 水 为溶剂， 反应 0.25h， 以100%的产率得到6-amino-1,3-dimethyl-5-(2-nitro-1-phenylethyl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  3d / 4f配位簇作为高非对映选择性迈克尔加成反应的合作催化剂

  摘要：

  迈克尔加成（MA）是合成化学中研究最深入的化学转化之一。在这里，我们报告的合成和晶体结构的3d / 4f配位簇（CCs）配制为[Zn II 2 Y III 2 L 4（solv）X（Z）Y ]并研究其对MA的催化性能。硝基苯乙烯与巴比妥酸衍生物。每个CC都具有两个临界的硬/软路易斯酸性Zn II中心和两个硬的路易斯酸性Y III中心中心位于缺陷的二分体拓扑中，使两种不同的金属相距约3.3Å。密度泛函理论的计算研究表明，这些四金属CC在溶液中解离生成两个催化活性二聚体，每个二聚体包含一种3d和一种4f协同作用的金属。催化作用的机制已通过NMR，电子顺磁共振和UV-vis得到了证实。本工作首次证明了3d / 4f CC在MA反应中作为高效，高非对映选择性催化剂的成功应用。

  DOI：

  10.1021/acs.inorgchem.7b01011

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.
• 3d/4f Coordination Clusters as Cooperative Catalysts for Highly Diastereoselective Michael Addition Reactions
  作者：Kieran Griffiths、Athanassios C. Tsipis、Prashant Kumar、Oliver P. E. Townrow、Alaa Abdul-Sada、Geoffrey R. Akien、Amgalanbaatar Baldansuren、Alan C. Spivey、George E. Kostakis

  DOI：10.1021/acs.inorgchem.7b01011

  日期：2017.8.21

  Michael addition (MA) is one of the most well studied chemical transformation in synthetic chemistry. Here, we report the synthesis and crystal structures of a library of 3d/4f coordination clusters (CCs) formulated as [ZnII2YIII2L4(solv)X(Z)Y] and study their catalytic properties toward the MA of nitrostyrenes with barbituric acid derivatives. Each CC presents two borderline hard/soft Lewis acidic

  迈克尔加成（MA）是合成化学中研究最深入的化学转化之一。在这里，我们报告的合成和晶体结构的3d / 4f配位簇（CCs）配制为[Zn II 2 Y III 2 L 4（solv）X（Z）Y ]并研究其对MA的催化性能。硝基苯乙烯与巴比妥酸衍生物。每个CC都具有两个临界的硬/软路易斯酸性Zn II中心和两个硬的路易斯酸性Y III中心中心位于缺陷的二分体拓扑中，使两种不同的金属相距约3.3Å。密度泛函理论的计算研究表明，这些四金属CC在溶液中解离生成两个催化活性二聚体，每个二聚体包含一种3d和一种4f协同作用的金属。催化作用的机制已通过NMR，电子顺磁共振和UV-vis得到了证实。本工作首次证明了3d / 4f CC在MA反应中作为高效，高非对映选择性催化剂的成功应用。