(2S,3S,E)-3-(1-(tert-butyldiphenylsilyl)pent-1-enyl)-N-phenyloxirane-2-carboxamide | 949164-33-4

• 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: (2S,3S,E)-3-(1-(tert-butyldiphenylsilyl)pent-1-enyl)-N-phenyloxirane-2-carboxamide
• 英文别名: (2S,3S)-3-[(E)-1-[tert-butyl(diphenyl)silyl]pent-1-enyl]-N-phenyloxirane-2-carboxamide
• CAS: 949164-33-4
• 化学式: C₃₀H₃₅NO₂Si
• 分子量: 469.699
• InChiKey: FJOLDZJUVNFZRM-ZNYSUIPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.72
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S,E)-3-(1-(tert-butyldiphenylsilyl)pent-1-enyl)-N-phenyloxirane-2-carboxamide 在 碘 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,5R)-4-(tert-butyldiphenylsilyl)-N-phenyl-5-propyl-2,5-dihydrofuran-2-carboxamide
  参考文献：
  名称：

  Aluminum-Catalyzed Enantio- and Diastereoselective Carbonyl Addition of Propargylsilanes. A New Approach to Enantioenriched Vinyl Epoxides

  摘要：

  A new pathway involving a Lewis acid-catalyzed carbonyl addition reaction of propargylsilanes and its subsequent development into a general enantio- and diastereoselective process are described. Aliphatic propargylsilanes with both saturated and unsaturated sidechains were effective nucleophiles affording highly functionalized chiral vinyl epoxides in good enantioselectivities (85-94% ee), excellent diastereoselectivities (> 99:1 E:Z; > 99:1 anti:syn) and in moderate to good yields (49-97%).

  DOI：

  10.1021/ja0740420
• 作为产物：
  描述：

  tert-butyldiphenyl-(1-propyl-propa-1,2-dienyl)silane 在 silver trifluoromethanesulfonate 正丁基锂 、 4 A molecular sieve 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 30.0h， 生成 (2S,3S,E)-3-(1-(tert-butyldiphenylsilyl)pent-1-enyl)-N-phenyloxirane-2-carboxamide
  参考文献：
  名称：

  Aluminum-Catalyzed Enantio- and Diastereoselective Carbonyl Addition of Propargylsilanes. A New Approach to Enantioenriched Vinyl Epoxides

  摘要：

  A new pathway involving a Lewis acid-catalyzed carbonyl addition reaction of propargylsilanes and its subsequent development into a general enantio- and diastereoselective process are described. Aliphatic propargylsilanes with both saturated and unsaturated sidechains were effective nucleophiles affording highly functionalized chiral vinyl epoxides in good enantioselectivities (85-94% ee), excellent diastereoselectivities (> 99:1 E:Z; > 99:1 anti:syn) and in moderate to good yields (49-97%).

  DOI：

  10.1021/ja0740420