tert-butyl 2-oxo-3-(pyridin-2-ylmethyl)indoline-1-carboxylate | 1229652-58-7

• 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: tert-butyl 2-oxo-3-(pyridin-2-ylmethyl)indoline-1-carboxylate
• CAS: 1229652-58-7
• 化学式: C₁₉H₂₀N₂O₃
• 分子量: 324.379
• InChiKey: WRDRTYDLFVZPNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  59.5
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 tert-butyl 2-oxo-3-(pyridin-2-ylmethyl)indoline-1-carboxylate 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， 生成 (S)-tert-butyl-3-(hydroxymethyl)-2-oxo-3-(pyridin-2-ylmethyl)indoline-1-carboxylate 、 (R)-tert-butyl-3-(hydroxymethyl)-2-oxo-3-(pyridin-2-ylmethyl)indoline-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 asymmetric Michael addition of 3-substituted oxindoles to α,β-unsaturated acyl phosphonates for the synthesis of 3,3′-disubstituted oxindoles with chiral squaramides
  作者：Lin Chen、Yong You、Ming-Liang Zhang、Jian-qiang Zhao、Jian Zuo、Xiao-Mei Zhang、Wei-Cheng Yuan、Xiao-Ying Xu

  DOI：10.1039/c5ob00317b

  日期：——

  The first Michael addition of 3-monosubstituted oxindoles to α,β-unsaturated acyl phosphonates is investigated to give 3,3′-disubstituted oxindoles with excellent results.

  第一次将3-单取代氧化吲哚加到α，β-不饱和酰基膦酸酯中进行的Michael加成反应被研究，结果表明可以获得3,3'-二取代氧化吲哚，且反应效果优异。