tert-butyl 4-(methoxymethoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethylcarbamate | 1192262-32-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: tert-butyl 4-(methoxymethoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethylcarbamate
• 英文别名: tert-butyl N-[2-[4-(methoxymethoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]carbamate
• CAS: 1192262-32-0
• 化学式: C₂₁H₃₄BNO₆
• 分子量: 407.315
• InChiKey: GHCIXSGHJBGACB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(methoxymethoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethylcarbamate 在 sodium periodate 、 ammonium acetate 、 水 作用下， 以 丙酮 为溶剂， 反应 15.0h， 以88%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
• 作为产物：
  描述：

  tert-butyl 3-iodo-4-(methoxymethoxy)phenethylcarbamate 、 频那醇硼烷 在 palladium diacetate 、 三乙胺 、 2-(二环己基膦基)联苯 作用下， 以 1,4-二氧六环 为溶剂， 以84%的产率得到tert-butyl 4-(methoxymethoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethylcarbamate
  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.