catechol [2-(diethylamino)carbonyl]-4-methyl-phenylboronate | 160758-63-4

• 英文名称: catechol [2-(diethylamino)carbonyl]-4-methyl-phenylboronate
• CAS: 160758-63-4
• 化学式: C₁₈H₂₀BNO₃
• 分子量: 309.173
• InChiKey: WNLROZVNOHNMFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
  None

反应信息

• 作为产物：
  描述：

  避蚊胺 在 TMEDA 、 sec-BuLi 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 catechol [2-(diethylamino)carbonyl]-4-methyl-phenylboronate
  参考文献：
  名称：

  Synthesis and structural investigation of two potential boronate affinity chromatography ligands catechol [2-(diisopropylamino)carbonyl]phenylboronate and catechol [2-(diethylamino)carbonyl, 4-methyl]phenylboronate

  摘要：

  Two potential boronate affinity chromatography ligands, catechol [2-(diisopropylamino)carbonyl]phenylboronate (I) and catechol [2-(diethylamino)carbonyl,4-methyl]phenylboronate (II) were synthesized by directed ortholithiation followed by boronation. Single crystal X-ray analyses of compounds I and II demonstrated an internal coordination bond between the boron atom and the carbonyl oxygen atom, rendering the boron atom environment to;be tetrahedral. In addition, B-11 NMR data also indicated that the boron environment is tetrahedral. The coordinated carbonyl oxygen-B bond length is 1.556(9) Angstrom compared to an average B-O bond length of 1.47 Angstrom to the catechol ligand. They are ideal models of a new type of ligands to study boronate affinity chromatography because they may esterify with catechols at neutral pH conditions.

  DOI：

  10.1016/0022-328x(94)05337-b