N-((S)-2-(naphthalen-1-yl)-1-((3aR,4R,6R,7aS)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)ethyl)acetamide | 173937-85-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-((S)-2-(naphthalen-1-yl)-1-((3aR,4R,6R,7aS)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)ethyl)acetamide
• CAS: 173937-85-4
• 化学式: C₂₄H₃₀BNO₃
• 分子量: 391.318
• InChiKey: PXALRCMBHDXWFM-BKSKZGTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-((S)-2-(naphthalen-1-yl)-1-((3aR,4R,6R,7aS)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)ethyl)acetamide 在 三氯化硼 、 水 作用下， 以 二氯甲烷 为溶剂， 生成 [(1S)-1-acetamido-2-(1-naphthyl)ethyl]boronic acid
  参考文献：
  名称：

  Synthesis and carbohydrate binding studies of fluorescent α-amidoboronic acids and the corresponding bisboronic acids

  摘要：

  Fluorescent boronic acids are very useful for the design and synthesis of carbohydrate sensors. In an earlier communication, we first described the effort of developing water soluble fluorescent alpha-amidoboronic acids, which change fluorescence upon sugar binding. In this report, we describe a general method of functionalizing such boronic acids and their applications in the preparation of bis-alpha-amidoboronic acids with significantly enhanced binding for oligosaccharides as compared to their monoboronic acid counterparts. The advantages of good water solubility, easy modification to generate diversity, and modularity in synthesis will make alpha-amidoboronic acids very useful building blocks for future synthesis of boronic acid-based fluorescent sensors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2010.01.017
• 作为产物：
  描述：

  、 乙酸酐 以 四氢呋喃 为溶剂， 生成 N-((S)-2-(naphthalen-1-yl)-1-((3aR,4R,6R,7aS)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)ethyl)acetamide
  参考文献：
  名称：

  Synthesis and carbohydrate binding studies of fluorescent α-amidoboronic acids and the corresponding bisboronic acids

  摘要：

  Fluorescent boronic acids are very useful for the design and synthesis of carbohydrate sensors. In an earlier communication, we first described the effort of developing water soluble fluorescent alpha-amidoboronic acids, which change fluorescence upon sugar binding. In this report, we describe a general method of functionalizing such boronic acids and their applications in the preparation of bis-alpha-amidoboronic acids with significantly enhanced binding for oligosaccharides as compared to their monoboronic acid counterparts. The advantages of good water solubility, easy modification to generate diversity, and modularity in synthesis will make alpha-amidoboronic acids very useful building blocks for future synthesis of boronic acid-based fluorescent sensors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2010.01.017