3-bromo-1-(toluene-4-sulfonyl)-1H-indole-4-carboxylic acid methyl ester | 1322744-51-3

• 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: 3-bromo-1-(toluene-4-sulfonyl)-1H-indole-4-carboxylic acid methyl ester
• 英文别名: Methyl 3-bromo-1-tosyl-1H-indole-4-carboxylate；methyl 3-bromo-1-(4-methylphenyl)sulfonylindole-4-carboxylate
• CAS: 1322744-51-3
• 化学式: C₁₇H₁₄BrNO₄S
• 分子量: 408.272
• InChiKey: YEENJUBEEBTPBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-bromo-1-(toluene-4-sulfonyl)-1H-indole-4-carboxylic acid methyl ester 、 N-((苄氧基)羰基)-3-碘-L-丙氨酸甲酯 在 三甲基氯硅烷 、 1,2-二溴乙烷 、 锌 、 tris-(dibenzylideneacetone)dipalladium(0) 、 1,2,3,4,5-五苯基-1′-(二叔丁基膦)二茂铁 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 以18%的产率得到(S)-3-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-1-(toluene-4-sulfonyl)-1H-indole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Convenient synthesis of chiral tryptophan derivatives using Negishi cross-coupling

  摘要：

  A facile synthetic procedure for chiral tryptophan derivatives using Negishi cross-coupling reaction of serine-derived iodoalanine with 3-haloindole is described. The best result was obtained when the reaction of N-tosyl-3-bromoindole with N-Cbz-iodoalanine methyl ester was carried out by the combination of Pd(2)(dba)(3) and sterically hindered ferrocenyl ligand Q-PHOS. This reaction condition not only gave the desired tryptophan derivative as high as 76% yield, but also suppressed the formation of undesired products, the dehalogenated indole and the homodimer of indole, which were difficult to separate. This reaction was extended to the synthesis of various tryptophan derivatives having substituents on the benzene ring. The characteristic of this reaction is the practical biomimetic synthesis of chiral tryptophan derivatives in one-step. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.053
• 作为产物：
  描述：

  4-methoxycarbonyl-1-<(4-methylphenyl)sulfonyl>-1H-indole 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 3-bromo-1-(toluene-4-sulfonyl)-1H-indole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Convenient synthesis of chiral tryptophan derivatives using Negishi cross-coupling

  摘要：

  A facile synthetic procedure for chiral tryptophan derivatives using Negishi cross-coupling reaction of serine-derived iodoalanine with 3-haloindole is described. The best result was obtained when the reaction of N-tosyl-3-bromoindole with N-Cbz-iodoalanine methyl ester was carried out by the combination of Pd(2)(dba)(3) and sterically hindered ferrocenyl ligand Q-PHOS. This reaction condition not only gave the desired tryptophan derivative as high as 76% yield, but also suppressed the formation of undesired products, the dehalogenated indole and the homodimer of indole, which were difficult to separate. This reaction was extended to the synthesis of various tryptophan derivatives having substituents on the benzene ring. The characteristic of this reaction is the practical biomimetic synthesis of chiral tryptophan derivatives in one-step. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.053