(S)-tert-butyl-3-(hydroxymethyl)-3-methyl-2-oxoindoline-1-carboxylate | 1229652-85-0

• 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)-tert-butyl-3-(hydroxymethyl)-3-methyl-2-oxoindoline-1-carboxylate
• 英文别名: tert-butyl (3S)-3-(hydroxymethyl)-3-methyl-2-oxoindole-1-carboxylate
• CAS: 1229652-85-0
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: LIAGZDSGUFWVTQ-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl-3-(hydroxymethyl)-3-methyl-2-oxoindoline-1-carboxylate 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以98%的产率得到(S)-tert-butyl-3-((tert-butyldimethylsilyloxy)methyl)-3-methyl-2-oxoindoline-1-carboxylate
  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：

  聚合甲醛 、 tert-butyl 3-methyl-2-oxoindoline-1-carboxylate 在 吡啶 、 scandium dodecyl sulfate 、 sodium dodecyl sulfate 、 (αS,α'S)-α,α'-双(叔丁基)-[2,2'-联吡啶]-6,6'-二甲醇 作用下， 以 水 为溶剂， 反应 24.0h， 生成 (R)-tert-butyl-3-(hydroxymethyl)-3-methyl-2-oxoindoline-1-carboxylate 、 (S)-tert-butyl-3-(hydroxymethyl)-3-methyl-2-oxoindoline-1-carboxylate
  参考文献：
  名称：

  手性Scan催化酮在水中的对映体选择性羟甲基化

  摘要：

  与福尔马林形成的形式：已在水中使用甲醛水溶液（福尔马林）开发了Scan催化的酮的对映体选择性羟甲基化方法。加入催化量的吡啶使得能够将酮直接用于不对称的羟甲基化反应中。

  DOI：

  10.1002/asia.200900442

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.
• Chiral Scandium-Catalyzed Enantioselective Hydroxymethylation of Ketones in Water
  作者：Shū Kobayashi、Masaya Kokubo、Katsuaki Kawasumi、Takashi Nagano

  DOI：10.1002/asia.200900442

  日期：2010.3.1

  Form with formalin: Scandium‐catalyzed enantioselective hydroxymethylation of ketones has been developed using aqueous formaldehyde (formalin) in water. The addition of a catalytic amount of pyridine enables the use of ketones directly in asymmetric hydroxymethylation reactions.

  与福尔马林形成的形式：已在水中使用甲醛水溶液（福尔马林）开发了Scan催化的酮的对映体选择性羟甲基化方法。加入催化量的吡啶使得能够将酮直接用于不对称的羟甲基化反应中。