ethyl 4,6-diphenylpyrimidin-2(1H)-thione-5-carboxylate | 1257325-64-6

• 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: ethyl 4,6-diphenylpyrimidin-2(1H)-thione-5-carboxylate
• 英文别名: ethyl 4,6-diphenyl-2-sulfanylidene-1H-pyrimidine-5-carboxylate
• CAS: 1257325-64-6
• 化学式: C₁₉H₁₆N₂O₂S
• 分子量: 336.414
• InChiKey: NYVAUHWVIPCBLB-UHFFFAOYSA-N

物化性质

• 熔点：
  148-150 °C
• 沸点：
  490.0±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  82.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 4,6-diphenylpyrimidin-2(1H)-thione-5-carboxylate 、 2,3,5-tri-O-benzoyl-D-ribofuranosyl fluoride 在 三氟化硼乙醚 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 1-2',3',5'-tri-O-benzoyl-β-D-ribopentofuranosyl-5-(ethoxycarbonyl)-4,6-diphenylpyrimidin-2-thione
  参考文献：
  名称：

  Synthesis of novel nucleosides and stereoselectivity of N-glycosidation

  摘要：

  An efficient synthetic route for novel nucleosides has been realized. We report the formation of alpha-isomers in spite of neighboring group participation by the benzoyl group at the 2-position in N-glycosidation as well as discuss the stereoselectivity observed. We also found that non-silylated pyrimidin-2(1H)-ones and pyrimidin-2(1H)-thiones having aromatic structures reacted with 1-fluororibose in the presence of a Lewis acid to give the corresponding nucleosides in good to high yield. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.017
• 作为产物：
  描述：

  2-oxo-4,6-diphenyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester 在 劳森试剂 、 甲烷 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 苯 为溶剂， 反应 3.0h， 生成 ethyl 4,6-diphenylpyrimidin-2(1H)-thione-5-carboxylate
  参考文献：
  名称：

  Synthesis of novel nucleosides and stereoselectivity of N-glycosidation

  摘要：

  An efficient synthetic route for novel nucleosides has been realized. We report the formation of alpha-isomers in spite of neighboring group participation by the benzoyl group at the 2-position in N-glycosidation as well as discuss the stereoselectivity observed. We also found that non-silylated pyrimidin-2(1H)-ones and pyrimidin-2(1H)-thiones having aromatic structures reacted with 1-fluororibose in the presence of a Lewis acid to give the corresponding nucleosides in good to high yield. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.017

文献信息

• Oxidative transformation of thiols to disulfides promoted by activated carbon–air system
  作者：Masahiko Hayashi、Ken-ichi Okunaga、Shunsuke Nishida、Kenjiro Kawamura、Kazuo Eda

  DOI：10.1016/j.tetlet.2010.10.070

  日期：2010.12

  Efficient oxidative transformation of thiols to disulfides took place in the presence of activated carbon under an oxygen (or air) atmosphere. The present oxidation method is available not only for a variety of thiols such as simple aromatic and aliphatic thiols but also for 3,4-dihydropyrimidin-2(1H)-thiones and N-Boc-l-cysteine.

  在氧气（或空气）气氛下，在存在活性炭的情况下，硫醇进行了有效的氧化转化为二硫化物。本氧化方法不仅可用于多种硫醇，例如简单的芳族和脂族硫醇，而且可用于3,4-二氢嘧啶-2（1 H）-硫酮和N- Boc- 1-半胱氨酸。
• O- and N-Glycosidation of d-glycals using Ferrier rearrangement under Mitsunobu reaction conditions. Application to N-nucleoside synthesis
  作者：Kyosuke Michigami、Masahiko Hayashi

  DOI：10.1016/j.tet.2011.11.084

  日期：2012.1

  We have disclosed the reaction of 3-hydroxy free glycals with O- or N-nucleophiles under Mitsunobu reaction conditions proceeded to produce 2,3-unsaturated glycosides in good to high yield and moderate stereoselectivity. The reaction would take place via allyloxycarbenium ion. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of novel nucleosides and stereoselectivity of N-glycosidation
  作者：Kyosuke Michigami、Satoshi Uchida、Miho Adachi、Masahiko Hayashi

  DOI：10.1016/j.tet.2012.11.017

  日期：2013.1

  An efficient synthetic route for novel nucleosides has been realized. We report the formation of alpha-isomers in spite of neighboring group participation by the benzoyl group at the 2-position in N-glycosidation as well as discuss the stereoselectivity observed. We also found that non-silylated pyrimidin-2(1H)-ones and pyrimidin-2(1H)-thiones having aromatic structures reacted with 1-fluororibose in the presence of a Lewis acid to give the corresponding nucleosides in good to high yield. (c) 2012 Elsevier Ltd. All rights reserved.