N-(1-benzyl-1H-indole-2-carbonyl)-4-methyl-N-(1-methylprop-2-ynyl)benzenesulfonamide | 1215220-66-8

• 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: N-(1-benzyl-1H-indole-2-carbonyl)-4-methyl-N-(1-methylprop-2-ynyl)benzenesulfonamide
• 英文别名: 1-benzyl-N-but-3-yn-2-yl-N-(4-methylphenyl)sulfonylindole-2-carboxamide
• CAS: 1215220-66-8
• 化学式: C₂₇H₂₄N₂O₃S
• 分子量: 456.565
• InChiKey: NRFJZZTVMMVRDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(1-benzyl-1H-indole-2-carbonyl)-4-methyl-N-(1-methylprop-2-ynyl)benzenesulfonamide 在 gold(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以58%的产率得到9-benzyl-3,4-dimethyl-2-(toluene-4-sulfonyl)-2,9-dihydro-β-carbolin-1-one
  参考文献：
  名称：

  Synthesis of substituted β-carbolines via gold(III)-catalyzed cycloisomerization of N-propargylamides

  摘要：

  Indole-substituted N-propargylamides undergo a gold(III)-catalyzed cyclization to give oxazoles or beta-carbolinones, depending on the Substitution pattern at the amide nitrogen. Secondary amides furnished oxazoles via a 5-exo-dig cyclization, while tertiary indole-2-carboxamides cycloisomerized to give 2,9-dihydro-beta-carbolin-1-ones upon treatment with catalytic amounts of gold(III) chloride. An optimized procedure was developed to prepare several new N-benzyl-beta-carbolinones as well as the corresponding beta-carbolines, which are of interest as core structures found in various natural products such as the harman, ervolanine, and lavendamycin class of alkaloids. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.033
• 作为产物：
  描述：

  1-benzyl-1H-indole-2-carboxylic acid chloride 、 N-(but-3-yn-2-yl)-4-methylbenzenesulfonamide 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以64%的产率得到N-(1-benzyl-1H-indole-2-carbonyl)-4-methyl-N-(1-methylprop-2-ynyl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis of substituted β-carbolines via gold(III)-catalyzed cycloisomerization of N-propargylamides

  摘要：

  Indole-substituted N-propargylamides undergo a gold(III)-catalyzed cyclization to give oxazoles or beta-carbolinones, depending on the Substitution pattern at the amide nitrogen. Secondary amides furnished oxazoles via a 5-exo-dig cyclization, while tertiary indole-2-carboxamides cycloisomerized to give 2,9-dihydro-beta-carbolin-1-ones upon treatment with catalytic amounts of gold(III) chloride. An optimized procedure was developed to prepare several new N-benzyl-beta-carbolinones as well as the corresponding beta-carbolines, which are of interest as core structures found in various natural products such as the harman, ervolanine, and lavendamycin class of alkaloids. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.033

文献信息

• Synthesis of substituted β-carbolines via gold(III)-catalyzed cycloisomerization of N-propargylamides
  作者：Guido Verniest、Dylan England、Norbert De Kimpe、Albert Padwa

  DOI：10.1016/j.tet.2009.10.033

  日期：2010.2

  Indole-substituted N-propargylamides undergo a gold(III)-catalyzed cyclization to give oxazoles or beta-carbolinones, depending on the Substitution pattern at the amide nitrogen. Secondary amides furnished oxazoles via a 5-exo-dig cyclization, while tertiary indole-2-carboxamides cycloisomerized to give 2,9-dihydro-beta-carbolin-1-ones upon treatment with catalytic amounts of gold(III) chloride. An optimized procedure was developed to prepare several new N-benzyl-beta-carbolinones as well as the corresponding beta-carbolines, which are of interest as core structures found in various natural products such as the harman, ervolanine, and lavendamycin class of alkaloids. (C) 2009 Elsevier Ltd. All rights reserved.