(R)-5-chloro-3-hydroxy-1-methyl-3-(2-phenylallyl)indolin-2-one | 1373320-77-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (R)-5-chloro-3-hydroxy-1-methyl-3-(2-phenylallyl)indolin-2-one
• 英文别名: (3R)-5-chloro-3-hydroxy-1-methyl-3-(2-phenylprop-2-enyl)indol-2-one
• CAS: 1373320-77-4
• 化学式: C₁₈H₁₆ClNO₂
• 分子量: 313.784
• InChiKey: HWTDYTJIJPBRGO-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-氯-1-甲基-1H-吲哚-2,3-二酮 、 三甲基(2-苯基丙-2-烯基)硅烷 在 三甲基氯硅烷 、 sodium hexafluoroantimonate 、 2,6-双[(3aS,8aR)-3a,8a-二氢-8H-indeno[1,2-d]恶唑啉-2-基]吡啶 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 乙腈 为溶剂， 反应 0.16h， 以88%的产率得到(R)-5-chloro-3-hydroxy-1-methyl-3-(2-phenylallyl)indolin-2-one
  参考文献：
  名称：

  Scandium(III)-Catalyzed Enantioselective Allylation of Isatins Using Allylsilanes

  摘要：

  The scandium(III)-catalyzed enantioselective Hosomi-Sakurai allylation of isatins with various substituted allylic silanes is described. A catalyst loading as low as 0.05 mol % Is utilized at room temperature to afford the 3-allyl-3-hydroxy-2-oxindoles in excellent yields and enantioselectivity up to 99% ee, including a demonstration of a gram-scale reaction. The effects of additives and varying silyl groups were explored to demonstrate the scope and application.

  DOI：

  10.1021/ol300496v

文献信息

• Scandium(III)-Catalyzed Enantioselective Allylation of Isatins Using Allylsilanes
  作者：Nadine V. Hanhan、Yng C. Tang、Ngon T. Tran、Annaliese K. Franz

  DOI：10.1021/ol300496v

  日期：2012.5.4

  The scandium(III)-catalyzed enantioselective Hosomi-Sakurai allylation of isatins with various substituted allylic silanes is described. A catalyst loading as low as 0.05 mol % Is utilized at room temperature to afford the 3-allyl-3-hydroxy-2-oxindoles in excellent yields and enantioselectivity up to 99% ee, including a demonstration of a gram-scale reaction. The effects of additives and varying silyl groups were explored to demonstrate the scope and application.