5-(2-(tert-butoxycarbonylamino)ethyl)-2-(methoxymethoxy)phenylboronic acid | 1192262-33-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(2-(tert-butoxycarbonylamino)ethyl)-2-(methoxymethoxy)phenylboronic acid
• 英文别名: [2-(Methoxymethoxy)-5-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]phenyl]boronic acid
• CAS: 1192262-33-1
• 化学式: C₁₅H₂₄BNO₆
• 分子量: 325.17
• InChiKey: LUWVVGPXJANNLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.42
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  97.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(2-(tert-butoxycarbonylamino)ethyl)-2-(methoxymethoxy)phenylboronic acid 、 Cbz-MeHis-OMe 在 [Cu(OH)TMEDA]2Cl₂ 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 以61%的产率得到(S)-methyl 2-((benzyloxycarbonyl)(methyl)amino)-3-(1-(5-(2-(tertbutoxycarbonylamino)ethyl)-2-(methoxymethoxy)phenyl)-1H-imidazol-4-yl)propanoate
  参考文献：
  名称：

  Synthesis of a Cyclic Pentapeptide Mimic of the Active Site His-Tyr Cofactor of Cytochrome c Oxidase

  摘要：

  Arylboronic acid based technology provides a mild, regioselective, and nontoxic N-arylation procedure for accessing the Unusual N-arylated side chain histidine found in the active site of cytochrome c oxidase (CcO) The N-arylated histidine is elaborated to the complete cytochrome c oxidase cyclic pentapeptide cofactor. Molecular modeling of the cofactor provides insight into the dynamic character of the N-aryl bond.

  DOI：

  10.1021/jo901744y
• 作为产物：
  描述：

  potassium (5-(2-(tert-butoxycarbonylamino)ethyl)-2-(methoxymethoxy)phenyl)trifluoroborate 在 水 、 lithium hydroxide 、 盐酸 、 氯化铵 作用下， 以 乙腈 、 水 为溶剂， 反应 20.0h， 以96%的产率得到5-(2-(tert-butoxycarbonylamino)ethyl)-2-(methoxymethoxy)phenylboronic acid
  参考文献：
  名称：

  Synthesis of a Cyclic Pentapeptide Mimic of the Active Site His-Tyr Cofactor of Cytochrome c Oxidase

  摘要：

  Arylboronic acid based technology provides a mild, regioselective, and nontoxic N-arylation procedure for accessing the Unusual N-arylated side chain histidine found in the active site of cytochrome c oxidase (CcO) The N-arylated histidine is elaborated to the complete cytochrome c oxidase cyclic pentapeptide cofactor. Molecular modeling of the cofactor provides insight into the dynamic character of the N-aryl bond.

  DOI：

  10.1021/jo901744y

文献信息

• Synthesis of a Cyclic Pentapeptide Mimic of the Active Site His-Tyr Cofactor of Cytochrome <i>c</i> Oxidase
  作者：Maximillian E. Mahoney、Allen Oliver、Ólöf Einarsdóttir、Joseph P. Konopelski

  DOI：10.1021/jo901744y

  日期：2009.11.6

  Arylboronic acid based technology provides a mild, regioselective, and nontoxic N-arylation procedure for accessing the Unusual N-arylated side chain histidine found in the active site of cytochrome c oxidase (CcO) The N-arylated histidine is elaborated to the complete cytochrome c oxidase cyclic pentapeptide cofactor. Molecular modeling of the cofactor provides insight into the dynamic character of the N-aryl bond.