4-(2-azido-7-(2,5-bis(tetrahydro-2H-pyran-2-yloxy)phenyl)heptylamino)-4-oxobutanoic acid | 1309932-14-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(2-azido-7-(2,5-bis(tetrahydro-2H-pyran-2-yloxy)phenyl)heptylamino)-4-oxobutanoic acid
• CAS: 1309932-14-6
• 化学式: C₂₇H₄₀N₄O₇
• 分子量: 532.637
• InChiKey: RVNYVXPDUGZSLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.26
• 重原子数：
  38.0
• 可旋转键数：
  16.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  152.08
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-(2-azido-7-(2,5-bis(tetrahydro-2H-pyran-2-yloxy)phenyl)heptylamino)-4-oxobutanoic acid 、 1,1,1-triphenyl-14,17,20,23,26-pentaoxa-2-thiadotriacontan-32-amine 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以75%的产率得到N1-(2-azido-7-(2,5-bis(tetrahydro-2H-pyran-2-yloxy)phenyl)heptyl)-N4-(1,1,1-triphenyl-14,17,20,23,26-pentaoxa-2-thiadotriacontan-32-yl)succinamide
  参考文献：
  名称：

  Redox-Switchable Surface for Controlling Peptide Structure

  摘要：

  A general surface chemistry strategy is described for the development of a new switchable material. The method modulates a surface-immobilized-molecules structure by using two orthogonal "click" reactions based on Huisgen cycloaddition and oxime chemistry, where the oxime linkage is redox active and switchable. We demonstrate this strategy by developing a noninvasive, biocompatible, in situ surface chemistry that is able to modulate the affinity of a cell-adhesive peptide to cell integrin receptors to study dynamic cell adhesion and cell migration in real time and as a new hide-and-reveal strategy for application in new types of smart biofouling biomaterials.

  DOI：

  10.1021/ja203198y
• 作为产物：
  描述：

  2,2'-(2-(5-(oxiran-2-yl)pentyl)-1,4-phenylene)bis(oxy)bis(tetrahydro-2H-pyran) 在 sodium azide 、 碳酸氢钠 、 三乙胺 、 肼 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 111.5h， 生成 4-(2-azido-7-(2,5-bis(tetrahydro-2H-pyran-2-yloxy)phenyl)heptylamino)-4-oxobutanoic acid
  参考文献：
  名称：

  Redox-Switchable Surface for Controlling Peptide Structure

  摘要：

  A general surface chemistry strategy is described for the development of a new switchable material. The method modulates a surface-immobilized-molecules structure by using two orthogonal "click" reactions based on Huisgen cycloaddition and oxime chemistry, where the oxime linkage is redox active and switchable. We demonstrate this strategy by developing a noninvasive, biocompatible, in situ surface chemistry that is able to modulate the affinity of a cell-adhesive peptide to cell integrin receptors to study dynamic cell adhesion and cell migration in real time and as a new hide-and-reveal strategy for application in new types of smart biofouling biomaterials.

  DOI：

  10.1021/ja203198y