1-benzhydryl-1H-pyrimidine-2,4-dione | 697237-44-8

• 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-benzhydryl-1H-pyrimidine-2,4-dione
• 英文别名: 1-(diphenylmethyl)uracil；1-(Diphenylmethyl)-1,3-dihydropyrimidine-2,4-dione；1-benzhydrylpyrimidine-2,4-dione
• CAS: 697237-44-8
• 化学式: C₁₇H₁₄N₂O₂
• 分子量: 278.31
• InChiKey: XKYBWMWINUDREB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  54.86
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-benzhydryl-1H-pyrimidine-2,4-dione 、 溴甲苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以94%的产率得到1-Benzhydryl-3-benzylpyrimidine-2,4-dione
  参考文献：
  名称：

  Benzhydryl as an Efficient Selective Nitrogen Protecting Group for Uracils

  摘要：

  Regioselective N-substitution of the less active nitrogen within uracil analogues has been achieved following preliminary N-protection at the more active N-position with a benzhydryl protecting group. This protecting group is stable to concentrated HCl (aqueous) at reflux temperature, TFA at room temperature, and Pd-C-catalyzed normal pressure hydrogenation at room temperature; the benzhydryl group can be removed quantitatively and selectively with a 10% triflic acid solution in TFA at 0 degreesC.

  DOI：

  10.1021/jo0485076
• 作为产物：
  描述：

  尿嘧啶 、 二苯基溴甲烷 在 N,O-双三甲硅基乙酰胺 、 碘 作用下， 以 乙腈 为溶剂， 以80%的产率得到1-benzhydryl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Benzhydryl as an Efficient Selective Nitrogen Protecting Group for Uracils

  摘要：

  Regioselective N-substitution of the less active nitrogen within uracil analogues has been achieved following preliminary N-protection at the more active N-position with a benzhydryl protecting group. This protecting group is stable to concentrated HCl (aqueous) at reflux temperature, TFA at room temperature, and Pd-C-catalyzed normal pressure hydrogenation at room temperature; the benzhydryl group can be removed quantitatively and selectively with a 10% triflic acid solution in TFA at 0 degreesC.

  DOI：

  10.1021/jo0485076

文献信息

• Regioselective synthesis of 1-allyl- and 1-arylmethyl uracil and thymine derivatives
  作者：Vaishali Malik、Palwinder Singh、Subodh Kumar

  DOI：10.1016/j.tet.2005.02.047

  日期：2005.4

  in the presence of I2 regioselectively provide 1-allyl-/1-arylmethyl-uracil and thymine derivatives. The secondary aryl alkyl and diaryl methyl halides with 1 provide chiral 1-arylalkyl/1-(diarylmethyl) uracil/thymine derivatives. The procedure has been extended to the synthesis of fluorescent uracil/thymine derivatives.

  在I 2存在下，在1,2-二氯乙烷中的2,4-双（三甲基甲硅烷氧基）嘧啶1与烯丙基卤化物和芳基甲基卤化物可以选择性地提供1-烯丙基/ 1-芳基甲基尿嘧啶和胸腺嘧啶衍生物。具有1的仲芳基烷基和二芳基甲基卤化物提供手性1-芳基烷基/ 1-（二芳基甲基）尿嘧啶/胸腺嘧啶衍生物。该程序已扩展到荧光尿嘧啶/胸腺嘧啶衍生物的合成。
• <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
• 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.
• US9181199B2
  申请人：——

  公开号：US9181199B2

  公开（公告）日：2015-11-10
• Benzhydryl as an Efficient Selective Nitrogen Protecting Group for Uracils
  作者：Fan Wu、Musole G. Buhendwa、Donald F. Weaver

  DOI：10.1021/jo0485076

  日期：2004.12.1

  Regioselective N-substitution of the less active nitrogen within uracil analogues has been achieved following preliminary N-protection at the more active N-position with a benzhydryl protecting group. This protecting group is stable to concentrated HCl (aqueous) at reflux temperature, TFA at room temperature, and Pd-C-catalyzed normal pressure hydrogenation at room temperature; the benzhydryl group can be removed quantitatively and selectively with a 10% triflic acid solution in TFA at 0 degreesC.