(S)-tert-butyl-3-(4-chlorobenzyl)-3-(hydroxymethyl)-2-oxoindoline-1-carboxylate | 1229652-63-4

• 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: (S)-tert-butyl-3-(4-chlorobenzyl)-3-(hydroxymethyl)-2-oxoindoline-1-carboxylate
• 英文别名: tert-butyl (3S)-3-[(4-chlorophenyl)methyl]-3-(hydroxymethyl)-2-oxoindole-1-carboxylate
• CAS: 1229652-63-4
• 化学式: C₂₁H₂₂ClNO₄
• 分子量: 387.863
• InChiKey: BUAWGVPFXJTUEZ-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-t-butoxycarbonyl-3-(4-chlorobenzyl)-2-oxindole 、 聚合甲醛 在 1-[(1R,2R)-2-(dimethylamino)-1,2-diphenylethyl]-3-(4-nitrophenyl)thiourea 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 15.0h， 以89%的产率得到(S)-tert-butyl-3-(4-chlorobenzyl)-3-(hydroxymethyl)-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

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.