(S)-3-((tert-butyldimethylsilyloxy)methyl)-3-methylindolin-2-one | 1229652-90-7

• 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: (S)-3-((tert-butyldimethylsilyloxy)methyl)-3-methylindolin-2-one
• 英文别名: (3S)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-methyl-1H-indol-2-one
• CAS: 1229652-90-7
• 化学式: C₁₆H₂₅NO₂Si
• 分子量: 291.466
• InChiKey: YDPXWCSWCVQYLJ-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-3-((tert-butyldimethylsilyloxy)methyl)-3-methylindolin-2-one 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.17h， 以92%的产率得到(S)-3-((tert-butyldimethylsilyloxy)methyl)-1,3-dimethylindolin-2-one
  参考文献：
  名称：

  Organocatalytic Enantioselective Hydroxymethylation of Oxindoles with Paraformaldehyde as C1 Unit

  摘要：

  A bifunctional thiourea-tertiary amine-catalyzed asymmetric hydroxymethylation of 3-substituted oxindoles using paraformaldehyde as the C1 unit was developed. A wide scope of oxindoles, bearing C3 sterically congested quaternary carbon centers, were smoothly obtained in good to excellent yields (up to 99%) and high enantioselectivities (up to 91% ee) under mild reaction conditions. A more significant feature of this approach employs cheap and readily available paraformaldehyde as a hydroxymethylation Cl unit, which is activated by chiral bifunctional thiourea organocatalysts.

  DOI：

  10.1021/jo100769n
• 作为产物：
  描述：

  (S)-tert-butyl-3-((tert-butyldimethylsilyloxy)methyl)-3-methyl-2-oxoindoline-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以98%的产率得到(S)-3-((tert-butyldimethylsilyloxy)methyl)-3-methylindolin-2-one
  参考文献：
  名称：

  Organocatalytic Enantioselective Hydroxymethylation of Oxindoles with Paraformaldehyde as C1 Unit

  摘要：

  A bifunctional thiourea-tertiary amine-catalyzed asymmetric hydroxymethylation of 3-substituted oxindoles using paraformaldehyde as the C1 unit was developed. A wide scope of oxindoles, bearing C3 sterically congested quaternary carbon centers, were smoothly obtained in good to excellent yields (up to 99%) and high enantioselectivities (up to 91% ee) under mild reaction conditions. A more significant feature of this approach employs cheap and readily available paraformaldehyde as a hydroxymethylation Cl unit, which is activated by chiral bifunctional thiourea organocatalysts.

  DOI：

  10.1021/jo100769n

文献信息

• Organocatalytic Enantioselective Hydroxymethylation of Oxindoles with Paraformaldehyde as C1 Unit
  作者：Xiong-Li Liu、Yu-Hua Liao、Zhi-Jun Wu、Lin-Feng Cun、Xiao-Mei Zhang、Wei-Cheng Yuan

  DOI：10.1021/jo100769n

  日期：2010.7.16

  A bifunctional thiourea-tertiary amine-catalyzed asymmetric hydroxymethylation of 3-substituted oxindoles using paraformaldehyde as the C1 unit was developed. A wide scope of oxindoles, bearing C3 sterically congested quaternary carbon centers, were smoothly obtained in good to excellent yields (up to 99%) and high enantioselectivities (up to 91% ee) under mild reaction conditions. A more significant feature of this approach employs cheap and readily available paraformaldehyde as a hydroxymethylation Cl unit, which is activated by chiral bifunctional thiourea organocatalysts.