(R)-3-allyl-3-hydroxy-5-(trifluoromethoxy)indolin-2-one | 1373320-74-1

• 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)-3-allyl-3-hydroxy-5-(trifluoromethoxy)indolin-2-one
• 英文别名: (3R)-3-hydroxy-3-prop-2-enyl-5-(trifluoromethoxy)-1H-indol-2-one
• CAS: 1373320-74-1
• 化学式: C₁₂H₁₀F₃NO₃
• 分子量: 273.212
• InChiKey: PWFXWFXGEIINFT-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-三氟甲氧基吲哚-2,3-二酮 、 烯丙基三甲基硅烷 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 22.08h， 生成 (R)-3-allyl-3-hydroxy-5-(trifluoromethoxy)indolin-2-one 、 (S)-3-allyl-3-hydroxy-5-(trifluoromethoxy)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.