N-[[1-(2,2-dimethylpropanoyl)indol-3-yl]methylidene]-4-methylbenzenesulfonamide | 1170012-89-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[[1-(2,2-dimethylpropanoyl)indol-3-yl]methylidene]-4-methylbenzenesulfonamide
• CAS: 1170012-89-1
• 化学式: C₂₁H₂₂N₂O₃S
• 分子量: 382.483
• InChiKey: XCNDZFQUYOYDRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  76.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[[1-(2,2-dimethylpropanoyl)indol-3-yl]methylidene]-4-methylbenzenesulfonamide 、 carbonic acid methyl ester 2-oxo-2-phenyl-ethyl ester 在 N-甲基吗啉 、 2,2'-联吡啶 、 magnesium(II) perchlorate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 [(1S,2S)-1-[1-(2,2-dimethylpropanoyl)indol-3-yl]-1-[(4-methylphenyl)sulfonylamino]-3-oxo-3-phenylpropan-2-yl] methyl carbonate 、
  参考文献：
  名称：

  Direct catalytic diastereoselective Mannich reactions: the synthesis of protected α-hydroxy-β-aminoketones

  摘要：

  The combination of Mg(ClO4)(2), 2,2'-bipyridine and N-methylmorpholine generates an effective catalyst system for the direct addition of alpha-carbonate-substituted ketones to aryl N-Ts imines. Methyl-carbonate-substituted ketones deliver acyclic alpha-hydroxy-beta-aminoketone derivates, while ketones Substituted with alpha-iso-propenyl-carbonates furnish cyclic carbamate adducts. In both cases the anti-configured Mannich products dominate. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.03.026

文献信息

• Direct catalytic diastereoselective Mannich reactions: the synthesis of protected α-hydroxy-β-aminoketones
  作者：Nikki E. Stainforth、Gary A. Cutting、Matthew P. John、Michael C. Willis

  DOI：10.1016/j.tetasy.2009.03.026

  日期：2009.5

  The combination of Mg(ClO4)(2), 2,2'-bipyridine and N-methylmorpholine generates an effective catalyst system for the direct addition of alpha-carbonate-substituted ketones to aryl N-Ts imines. Methyl-carbonate-substituted ketones deliver acyclic alpha-hydroxy-beta-aminoketone derivates, while ketones Substituted with alpha-iso-propenyl-carbonates furnish cyclic carbamate adducts. In both cases the anti-configured Mannich products dominate. (C) 2009 Elsevier Ltd. All rights reserved.