2-(2-allylsulfanylethyl)-6-dimethylaminobenzo[de]isoquinoline-1,3-dione | 1235998-37-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-(2-allylsulfanylethyl)-6-dimethylaminobenzo[de]isoquinoline-1,3-dione
• CAS: 1235998-37-4
• 化学式: C₁₉H₂₀N₂O₂S
• 分子量: 340.446
• InChiKey: QHKSLRDGCMGLAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  40.62
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-hydroxy-N-((S)-1-methoxycarbonylethyl)-2,2-dimethylsuccinamidic acid but-3-enyl ester 、 2-(2-allylsulfanylethyl)-6-dimethylaminobenzo[de]isoquinoline-1,3-dione 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 水 、 叔丁醇 为溶剂， 以68%的产率得到3-hydroxy-N-((S)-1-methoxycarbonylethyl)-2,2-dimethylsuccinamidic acid (Z)-5-[2-(6-dimethylamino-1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)ethylsulfanyl]pent-3-enyl ester
  参考文献：
  名称：

  Functionalization of Peptides and Proteins by Mukaiyama Aldol Reaction

  摘要：

  The scope of the catalyst-free water-based Mukaiyama aldol reaction was explored through its application to the site-selective functionalization of N-terminal aldehydes of peptides and proteins. Various functional groups were introduced under mild and environmentally friendly conditions, with the first demonstration of aldol C-C bond formation in protein labeling studies. The efficiency and speed achieved in protein labeling can be of special interest in chemical biology studies.

  DOI：

  10.1021/ja102733a
• 作为产物：
  描述：

  烯丙硫醇 、 2-(2-bromoethyl)-6-dimethylaminobenzo[de]isoquinoline-1,3-dione 在 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.17h， 以87%的产率得到2-(2-allylsulfanylethyl)-6-dimethylaminobenzo[de]isoquinoline-1,3-dione
  参考文献：
  名称：

  Functionalization of Peptides and Proteins by Mukaiyama Aldol Reaction

  摘要：

  The scope of the catalyst-free water-based Mukaiyama aldol reaction was explored through its application to the site-selective functionalization of N-terminal aldehydes of peptides and proteins. Various functional groups were introduced under mild and environmentally friendly conditions, with the first demonstration of aldol C-C bond formation in protein labeling studies. The efficiency and speed achieved in protein labeling can be of special interest in chemical biology studies.

  DOI：

  10.1021/ja102733a