(S)-3-[(S)-1-(p-methylbenzenesulfonylamino)-1-(benzo[d][1,3]dioxol-5-yl)methyl]-3-methylindolin-2-one | 1160644-94-9

• 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)-1-(p-methylbenzenesulfonylamino)-1-(benzo[d][1,3]dioxol-5-yl)methyl]-3-methylindolin-2-one
• 英文别名: N-[(S)-1,3-benzodioxol-5-yl-[(3S)-3-methyl-2-oxo-1H-indol-3-yl]methyl]-4-methylbenzenesulfonamide
• CAS: 1160644-94-9
• 化学式: C₂₄H₂₂N₂O₅S
• 分子量: 450.515
• InChiKey: WSQCMUDPVBXNOA-UPVQGACJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-甲基羟基吲哚 、 N-[1-Benzo[1,3]dioxol-5-yl-meth-(E)-ylidene]-4-methyl-benzenesulfonamide 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， 反应 48.0h， 生成 (R)-3-[(R)-1-(p-methylbenzenesulfonylamino)-1-(benzo[d][1,3]dioxol-5-yl)methyl]-3-methylindolin-2-one 、 (S)-3-[(S)-1-(p-methylbenzenesulfonylamino)-1-(benzo[d][1,3]dioxol-5-yl)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.