3-(diethylamino)-5-methyl-1H-1l4,2l3-benzo[c][1,2]oxaborole-1,1-diol | 160758-67-8

• 英文名称: 3-(diethylamino)-5-methyl-1H-1l4,2l3-benzo[c][1,2]oxaborole-1,1-diol
• CAS: 160758-67-8
• 化学式: C₁₂H₁₈BNO₃
• 分子量: 235.091
• InChiKey: PSZULSKBBABESF-UHFFFAOYSA-N

计算性质

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

反应信息

• 作为反应物：
  描述：

  3-(diethylamino)-5-methyl-1H-1l4,2l3-benzo[c][1,2]oxaborole-1,1-diol 、 邻苯二酚 以 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
• 作为产物：
  描述：

  硼酸三甲酯 、 避蚊胺 在 TMEDA 、 sec-BuLi 作用下， 以 四氢呋喃 为溶剂， 生成 3-(diethylamino)-5-methyl-1H-1l4,2l3-benzo[c][1,2]oxaborole-1,1-diol
  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