2-diazo-4-phenyl-but-3-enoic acid 2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl ester | 760961-05-5

• 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: 2-diazo-4-phenyl-but-3-enoic acid 2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl ester
• 英文别名: 2-[2-(2-methoxyethoxy)ethoxy]ethyl (E)-2-diazo-4-phenylbut-3-enoate
• CAS: 760961-05-5
• 化学式: C₁₇H₂₂N₂O₅
• 分子量: 334.372
• InChiKey: XQNNQZDZBFIVIY-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  56
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-甲基吲哚 、 2-diazo-4-phenyl-but-3-enoic acid 2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl ester 在 dirhodium tetraacetate 、 盐酸羟胺 作用下， 以 乙二醇 、 乙酸乙酯 为溶剂， 反应 17.0h， 生成 2-hydroxy-4-phenyl-but-3-enoic acid 2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl ester 、 5-phenyl-1H-pyrazole-3-carboxylic acid 2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl ester 、 2-(3-methyl-indol-1-yl)-4-phenyl-but-3-enoic acid 2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl ester 、 2-(3-methyl-1H-indol-2-yl)-4-phenyl-but-3-enoic acid 2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl ester
  参考文献：
  名称：

  Selective Tryptophan Modification with Rhodium Carbenoids in Aqueous Solution

  摘要：

  A new transition metal-based reaction has been developed for the selective modification of tryptophan residues on protein substrates. After activation of vinyl-substituted diazo compounds by Rh2(OAc)4, the resulting metallocarbenoid intermediates were found to modify indoles in aqueous media despite competing reactions with water. Both N- and 2-substituted indole products were observed in the reaction. Following initial small-molecule studies, the reaction was performed on two protein substrates. Both myoglobin and subtilisin Carlsberg were modified readily in aqueous solution, and the tryptophan selectivity of the reactions was confirmed through MS analyses of trypsin digest fragments. It was also demonstrated that myoblobin concentrations as low as 10 muM still led to appreciable levels of modification. Reconstitution experiments confirmed that myoglobin retained its ability to bind heme following modification.

  DOI：

  10.1021/ja047272c
• 作为产物：
  描述：

  三甘醇单甲醚 在 4-二甲氨基吡啶 、 4-乙酰氨基苯磺酰叠氮 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 9.5h， 生成 2-diazo-4-phenyl-but-3-enoic acid 2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl ester
  参考文献：
  名称：

  Selective Tryptophan Modification with Rhodium Carbenoids in Aqueous Solution

  摘要：

  A new transition metal-based reaction has been developed for the selective modification of tryptophan residues on protein substrates. After activation of vinyl-substituted diazo compounds by Rh2(OAc)4, the resulting metallocarbenoid intermediates were found to modify indoles in aqueous media despite competing reactions with water. Both N- and 2-substituted indole products were observed in the reaction. Following initial small-molecule studies, the reaction was performed on two protein substrates. Both myoglobin and subtilisin Carlsberg were modified readily in aqueous solution, and the tryptophan selectivity of the reactions was confirmed through MS analyses of trypsin digest fragments. It was also demonstrated that myoblobin concentrations as low as 10 muM still led to appreciable levels of modification. Reconstitution experiments confirmed that myoglobin retained its ability to bind heme following modification.

  DOI：

  10.1021/ja047272c