(S)-3-[(S,E)-1-(p-methylbenzenesulfonylamino)-1-(2-phenylvinyl)methyl]-3-methylindolin-2-one | 1160644-97-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-3-[(S,E)-1-(p-methylbenzenesulfonylamino)-1-(2-phenylvinyl)methyl]-3-methylindolin-2-one
• 英文别名: 4-methyl-N-[(E,1S)-1-[(3S)-3-methyl-2-oxo-1H-indol-3-yl]-3-phenylprop-2-enyl]benzenesulfonamide
• CAS: 1160644-97-2
• 化学式: C₂₅H₂₄N₂O₃S
• 分子量: 432.543
• InChiKey: SAPBNPLOJAQINI-HAJQFONZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-甲基羟基吲哚 、 苯磺酰胺,4-甲基-N-(3-苯基-2-亚丙烯基)-,(E,E)- 在 4-((R)-(phenanthren-9-yloxy)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methyl)quinolin-6-ol 作用下， 以 氯仿 为溶剂， 生成 3-[(E)-1-(p-methylbenzenesulfonylamino)-1-(2-phenylvinyl)methyl]-3-methylindolin-2-one 、 (S)-3-[(S,E)-1-(p-methylbenzenesulfonylamino)-1-(2-phenylvinyl)methyl]-3-methylindolin-2-one 、 (R)-3-[(R,E)-1-(p-methylbenzenesulfonylamino)-1-(2-phenylvinyl)methyl]-3-methylindolin-2-one
  参考文献：
  名称：

  Enantioselective Organocatalytic anti-Mannich-Type Reaction of N-Unprotected 3-Substituted 2-Oxindoles with Aromatic N-Ts-aldimines

  摘要：

  The modified cinchona alkaloid-catalyzed direct Mannich-type reaction of N-unprotected 2-oxindoles with N-Ts-imine was developed to afford anti-3,3-disubstituted 2-oxindoles with vicinal chiral quaternary and tertiary carbon centers in yields up to 90% with excellent diastereoselectivities (antil syn up to 95:5) and good enantioselectivies (up to 89% ee). A transition model for the anti-diastereo- and enantioselectivity of the reaction was proposed.

  DOI：

  10.1021/jo9006688

文献信息

• Enantioselective Organocatalytic <i>anti</i>-Mannich-Type Reaction of <i>N</i>-Unprotected 3-Substituted 2-Oxindoles with Aromatic <i>N</i>-Ts-aldimines
  作者：Liang Cheng、Li Liu、Han Jia、Dong Wang、Yong-Jun Chen

  DOI：10.1021/jo9006688

  日期：2009.6.19

  The modified cinchona alkaloid-catalyzed direct Mannich-type reaction of N-unprotected 2-oxindoles with N-Ts-imine was developed to afford anti-3,3-disubstituted 2-oxindoles with vicinal chiral quaternary and tertiary carbon centers in yields up to 90% with excellent diastereoselectivities (antil syn up to 95:5) and good enantioselectivies (up to 89% ee). A transition model for the anti-diastereo- and enantioselectivity of the reaction was proposed.