3-(hydroxymethyl)-1,3-dimethylindolin-2-one | 210642-73-2

• 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: 3-(hydroxymethyl)-1,3-dimethylindolin-2-one
• 英文别名: (S)-3-(hydroxymethyl)-1,3-dimethylindolin-2-one；(3S)-3-(hydroxymethyl)-1,3-dimethylindol-2-one
• CAS: 210642-73-2
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: QOIAGHZMCYOZIB-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (S)-3-((tert-butyldimethylsilyloxy)methyl)-1,3-dimethylindolin-2-one 在 盐酸 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 10.0h， 以96%的产率得到3-(hydroxymethyl)-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

文献信息

• Palladium‐Catalysed Carboborylation for the Synthesis of Borylated Indanes
  作者：Andrzej Zieba、Joel F. Hooper

  DOI：10.1002/ejoc.202100309

  日期：2021.8.6

  The interception of σ-alkyl-palladium complexes in catalysis is a powerful strategy for the generation of molecular complexity. We have demonstrated a palladium-catalysed carboborylation reaction for the synthesis of borylated indanes, which proceeds in good yields and moderate enantioselectivity.

  σ-烷基-钯配合物在催化中的拦截是产生分子复杂性的有力策略。我们已经证明了用于合成硼化茚满的钯催化的碳硼化反应，该反应以良好的产率和适度的对映选择性进行。