1-(4-tert-butylbenzyl)-1H-pyrimidine-2,4-dione | 915316-24-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-tert-butylbenzyl)-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(4-Tert-butylphenyl)methyl]pyrimidine-2,4-dione
• CAS: 915316-24-4
• 化学式: C₁₅H₁₈N₂O₂
• 分子量: 258.32
• InChiKey: YDCRHLKTJJJART-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-tert-butylbenzyl)-1H-pyrimidine-2,4-dione 、 2-氯乙酰苯胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以90%的产率得到2-{3-[(4-tert-butylphenyl)methyl]-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-1-yl}-N-phenylacetamide
  参考文献：
  名称：

  A highly facile approach to the synthesis of novel 2-(3-benzyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-N-phenylacetamides

  摘要：

  A series of heterocyclic compounds were designed as potential nonnucleoside HIV reverse transcriptase inhibitors. Although the compounds ultimately proved inactive against HIV, during the course of the synthesis, a new and highly facile method to realize N-phenylacetamides was developed. Notably, the new route avoids the intractable workups and byproducts previously reported procedures have been associated with, thereby making this approach highly attractive to adaptation with other heterocyclics. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.090
• 作为产物：
  描述：

  4-叔丁基苄溴 、 尿嘧啶 在 N,O-双三甲硅基乙酰胺 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 1-(4-tert-butylbenzyl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Selective product amplification of thymine photodimer by recognition-directed supramolecular assistance

  摘要：

  合成了两种对称的双位点超分子模板（1和2），每种模板都呈现出两个氢键识别子单元。每个这样的子单元包含相同的供体和受体模式，能够与具有互补氢键基团的底物分子结合，形成超分子复合物。例如胸腺嘧啶或尿嘧啶衍生物等底物分子，与受体形成2 : 1的复合物，每个子单元通过两个氢键在理想方向上结合，便于光照射后发生[2 + 2]二聚化反应。客体核碱基在模板裂隙内的定向排列有利于选择性syn光产物形成，同时抑制trans异构体。互补的供体和受体氢键诱导的底物定位以及模板裂隙内的空间位阻是选择性产物形成的原因。

  DOI：

  10.1039/b605658j

文献信息

• <scp>DABCO</scp> mediated one pot synthesis of 2‐(3‐benzyl‐2, 6‐dioxo‐3, 6‐dihydropyrimidin‐1[ <scp>2</scp> <i>H</i> ]‐yl)‐ <i>N</i> ‐(4‐(1, <scp>3‐dioxo‐1</scp> <i>H</i> ‐benzo [ <i>de</i> ]isoquinolin‐2[ <scp>3</scp> <i>H</i> ]‐yl) aryl) acetamides as antimicrobial agents
  作者：Rambabu Sirgamalla、Kurumanna Adem、Sakram Boda、Ashok Kommakula、Suryam Neradi、Shyam Perka、Kiran Bojja、Mohammed Arifuddin

  DOI：10.1002/jhet.4055

  日期：——

  We report herein DABCO mediated one pot synthesis of 2‐(3‐benzyl‐2, 6‐dioxo‐3,6‐dihydropyrimidin‐1[2H]‐yl)‐N‐(4‐(1,3‐dioxo‐1H‐benzo[de]isoquinolin‐2[3H]‐yl) aryl) acetamides (4a‐j). The silent features of this new one pot synthesis include the shorter reaction time, high yields, simple workup, and simultaneous formation of N‐Amide and N‐benzyl bonds in the one pot. The newly synthesized compounds (4a‐j)

  我们在此报告DABCO介导的一锅合成2-（3-苄基-2-，2,6-二氧代-3-，6-二氢嘧啶-1 [2H] -基）-N-（4-（1，3-二氧代-1H-苯并[[]]异喹啉-2 [3H]-基）芳基）乙酰胺（4a-j）。这种新的一锅合成方法的沉默特性包括反应时间更短，产率高，后处理简单以及在一个锅中同时形成N-氨基和N-苄基键。新合成的化合物（4a-j）通过不同的光谱技术进行表征，例如IR，1 H-NMR，13C-NMR，HRMS。对所有合成的化合物的抗菌和抗真菌活性进行了评估。抗菌活性结果表明，化合物4a，4g，4i和4j对金黄色葡萄球菌最具活性。在枯草芽孢杆菌的情况下，发现化合物4a，4i和4j最具活性。化合物4c，4e，4i和4j对大肠杆菌的活性最高。对于铜绿假单胞菌 4a，4i和4j被发现更活跃。另一方面，抗真菌活性结果表明化合物4d，4f，4i和4j对黑曲霉具有更高的活性。发现化合物4
• Visible Light‐Induced Imide Alkylation of Azauracils with Aryl Diazoesters
  作者：Sudhir Kumar Hota、Sandip Murarka

  DOI：10.1002/asia.202301027

  日期：2024.2

  additive-free visible light-induced N−H functionalization of (aza)uracils with α-diazo esters leading to imide alkylation in good to excellent yields. The reaction proceeds through a N−H insertion in dichloromethane as a solvent, whereas, a photochemical three-component coupling product was obtained upon performing the reaction in cyclic ethers (1,4-dioxane, THF) as a solvent.

  我们开发了一种不含金属和添加剂的可见光诱导的（氮杂）尿嘧啶与 α-重氮酯的 NH 官能化，导致酰亚胺烷基化，收率良好至优异。该反应通过在二氯甲烷作为溶剂中进行NH插入进行，而在环醚（1,4-二恶烷，THF）作为溶剂中进行反应时得到光化学三组分偶联产物。
• Selective product amplification of thymine photodimer by recognition-directed supramolecular assistance
  作者：W. G. Skene、Volker Berl、H?l?ne Risler、Richard Khoury、Jean-Marie Lehn

  DOI：10.1039/b605658j

  日期：——

  Two symmetric ditopic supramolecular templates (1 and 2) each presenting two hydrogen bonding recognition subunits were synthesized. Each such subunit comprises the same donor and acceptor pattern, capable of binding a substrate molecule with complementary hydrogen bonding groups to form a supramolecular complex. Substrate molecules, such as thymine or uracil derivatives, yield 2 : 1 complexes with the acceptors involving two hydrogen bonds to each subunit with ideal orientation for subsequent [2 + 2] dimerization upon photoirradiation. Selective syn photoproduct formation and concomitant suppression of the trans isomer are favored by orientation of the two guest nucleobases within the template cleft. Complementary donor and acceptor hydrogen bonding induced positioning of the two substrates and steric hindrance within the template clefts are responsible for the selective product formation.

  合成了两种对称的双位点超分子模板（1和2），每种模板都呈现出两个氢键识别子单元。每个这样的子单元包含相同的供体和受体模式，能够与具有互补氢键基团的底物分子结合，形成超分子复合物。例如胸腺嘧啶或尿嘧啶衍生物等底物分子，与受体形成2 : 1的复合物，每个子单元通过两个氢键在理想方向上结合，便于光照射后发生[2 + 2]二聚化反应。客体核碱基在模板裂隙内的定向排列有利于选择性syn光产物形成，同时抑制trans异构体。互补的供体和受体氢键诱导的底物定位以及模板裂隙内的空间位阻是选择性产物形成的原因。
• A highly facile approach to the synthesis of novel 2-(3-benzyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-N-phenylacetamides
  作者：Mikhail S. Novikov、Denis A. Babkov、Maria P. Paramonova、Alexander O. Chizhov、Anastasia L. Khandazhinskaya、Katherine L. Seley-Radtke

  DOI：10.1016/j.tetlet.2012.11.090

  日期：2013.2

  A series of heterocyclic compounds were designed as potential nonnucleoside HIV reverse transcriptase inhibitors. Although the compounds ultimately proved inactive against HIV, during the course of the synthesis, a new and highly facile method to realize N-phenylacetamides was developed. Notably, the new route avoids the intractable workups and byproducts previously reported procedures have been associated with, thereby making this approach highly attractive to adaptation with other heterocyclics. (c) 2012 Elsevier Ltd. All rights reserved.