1-二苯甲基-5-甲基嘧啶-2,4-二酮 | 696617-65-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-二苯甲基-5-甲基嘧啶-2,4-二酮
• 英文名称: 1-benzhydrylthymine
• 英文别名: 1-benzhydryl-5-methyl-1H-pyrimidine-2,4-dione；1-benzhydryl-5-methyl-2,4(1H,3H)-pyrimidinedione；1-benzhydryl-5-methylpyrimidine-2,4-dione
• CAS: 696617-65-9
• 化学式: C₁₈H₁₆N₂O₂
• mdl: MFCD04220783
• 分子量: 292.337
• InChiKey: IIBBCXBSHWRASL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  1-二苯甲基-5-甲基嘧啶-2,4-二酮 在 三氟甲磺酸 作用下， 以 三氟乙酸 为溶剂， 生成 Ethyl thyminylacetate
  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：

  胸腺嘧啶 、 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95%的产率得到1-二苯甲基-5-甲基嘧啶-2,4-二酮
  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。
• 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.