1-benzyl-3'-methyl-3'-phenylspiro[indoline-3,2'-oxetane]-2,4'-dione | 1505519-13-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 1-benzyl-3'-methyl-3'-phenylspiro[indoline-3,2'-oxetane]-2,4'-dione
• 英文别名: (3S,3'S)-1-benzyl-3'-methyl-3'-phenylspiro[indole-3,4'-oxetane]-2,2'-dione
• CAS: 1505519-13-0
• 化学式: C₂₄H₁₉NO₃
• 分子量: 369.42
• InChiKey: IDLBICGGNDIFNF-DNQXCXABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.94
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1-苄基-1H-吲哚-2,3-二酮 、 methyl phenyl ketene 在 C₃₉H₆₀N₄O₄ 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 1-benzyl-3'-methyl-3'-phenylspiro[indoline-3,2'-oxetane]-2,4'-dione
  参考文献：
  名称：

  Chiral Lewis Acid Catalyzed Asymmetric Cycloadditions of Disubstituted Ketenes for the Synthesis of β-Lactones and δ-Lactones

  摘要：

  Highly diastereo- and enantioselective [2 + 2]- and [4 + 2]-cycloadditions of disubstituted ketenes were realized by chiral Lewis acid catalysis. A series of arylalkylketenes underwent the reaction smoothly with isatins and beta,gamma-unsaturated alpha-ketoesters, providing optically active beta-lactones and delta-lactones with vicinal chiral centers in excellent yields (up to 99%) and enantioselectivities (up to 99% ee), as well as exclusively high diastereoselectivities under 0.2-2 mol % catalyst loading.

  DOI：

  10.1021/ol4031217