(E)-benzyl 5-(methoxycarbonyloxy)-1-(4-nitrophenyl)pent-3-enyl(tosylcarbamoyl)carbamate | 1245904-44-2

• 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: (E)-benzyl 5-(methoxycarbonyloxy)-1-(4-nitrophenyl)pent-3-enyl(tosylcarbamoyl)carbamate
• CAS: 1245904-44-2
• 化学式: C₂₉H₂₉N₃O₁₀S
• 分子量: 611.629
• InChiKey: SWRYJPCEGVVOLG-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  43.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  171.45
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (E)-benzyl 5-(methoxycarbonyloxy)-1-(4-nitrophenyl)pent-3-enyl(tosylcarbamoyl)carbamate 在 四(三苯基膦)钯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 anti-benzyl 6-(4-nitrophenyl)-2-oxo-3-tosyl-4-vinyltetrahydropyrimidine-1(2H)-carboxylate 、 syn-benzyl 6-(4-nitrophenyl)-2-oxo-3-tosyl-4-vinyltetrahydropyrimidine-1(2H)-carboxylate
  参考文献：
  名称：

  Stereodivergent Synthesis of 1,3-syn- and -anti-Tetrahydropyrimidinones

  摘要：

  An efficient protocol for the stereoselective synthesis of 1,3-syn and -anti-tetrahydropyrimidinones (syn- and anti-11a) is reported The modular procedure is based on a stereodivergent cyclization of readily available urea-type substrates (10a) by intramolecular allylic substitution The cyclization proceeds with excellent yield (up to 99%) and selectivity (up to dr > 20:1), purely based on substrate control The product pyrimidines can be readily transformed into the corresponding free syn- and anti-amines

  DOI：

  10.1021/ol101755m
• 作为产物：
  描述：

  (E)-benzyl 5-(methoxycarbonyloxy)-1-(4-nitrophenyl)pent-3-enylcarbamate 、 对甲基苯磺酰异氰酸酯 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.33h， 以43%的产率得到(E)-benzyl 5-(methoxycarbonyloxy)-1-(4-nitrophenyl)pent-3-enyl(tosylcarbamoyl)carbamate
  参考文献：
  名称：

  Stereodivergent Synthesis of 1,3-syn- and -anti-Tetrahydropyrimidinones

  摘要：

  An efficient protocol for the stereoselective synthesis of 1,3-syn and -anti-tetrahydropyrimidinones (syn- and anti-11a) is reported The modular procedure is based on a stereodivergent cyclization of readily available urea-type substrates (10a) by intramolecular allylic substitution The cyclization proceeds with excellent yield (up to 99%) and selectivity (up to dr > 20:1), purely based on substrate control The product pyrimidines can be readily transformed into the corresponding free syn- and anti-amines

  DOI：

  10.1021/ol101755m