2-cyano-3-[4'-(4'',4'',5'',5''-tetramethyl-1'',3'',2''-dioxaborolan-2''-yl)phenyl]-2-(4''-trifluoromethoxyphenyldiazo)propionitrile | 1225050-04-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-cyano-3-[4'-(4'',4'',5'',5''-tetramethyl-1'',3'',2''-dioxaborolan-2''-yl)phenyl]-2-(4''-trifluoromethoxyphenyldiazo)propionitrile
• 英文别名: 2-[[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl]-2-[[4-(trifluoromethoxy)phenyl]diazenyl]propanedinitrile；2-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl]-2-[[4-(trifluoromethoxy)phenyl]diazenyl]propanedinitrile
• CAS: 1225050-04-3
• 化学式: C₂₃H₂₂BF₃N₄O₃
• 分子量: 470.259
• InChiKey: QEBXPZWNGAGFEU-UHFFFAOYSA-N

物化性质

• 熔点：
  120-122 °C
• 沸点：
  525.3±50.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-cyano-3-[4'-(4'',4'',5'',5''-tetramethyl-1'',3'',2''-dioxaborolan-2''-yl)phenyl]-2-(4''-trifluoromethoxyphenyldiazo)propionitrile 在 水 、 双氧水 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 对羟基苯甲醇 、
  参考文献：
  名称：

  Caged mitochondrial uncouplers that are released in response to hydrogen peroxide

  摘要：

  Caged versions of the most common mitochondrial uncouplers (proton translocators) have been prepared that sense the reactive oxygen species (ROS) hydrogen peroxide to release the uncouplers 2,4-dinitrophenol (DNP) and carbonylcyanide p-trifluoromethoxyphenylhydrazone (FCCP) from caged states with second order rate constants of 10 (+/- 0.8) M(-1) s(-1) and 64.8 (+/- 0.6) M(-1) s(-1), respectively. The trigger mechanism involves conversion of an arylboronate into a phenol followed by fragmentation. Hydrogen peroxide-activated uncouplers may be useful for studying the biological process of ageing. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.01.103
• 作为产物：
  描述：

  2-cyano-3-[4'-(4'',4'',5'',5''-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propionitrile 、 对三氟甲氧基苯胺 在 盐酸 、 sodium nitrite 、 sodium acetate 作用下， 以 水 、 甲醇 、 乙醇 为溶剂， 反应 0.08h， 以46%的产率得到2-cyano-3-[4'-(4'',4'',5'',5''-tetramethyl-1'',3'',2''-dioxaborolan-2''-yl)phenyl]-2-(4''-trifluoromethoxyphenyldiazo)propionitrile
  参考文献：
  名称：

  Caged mitochondrial uncouplers that are released in response to hydrogen peroxide

  摘要：

  Caged versions of the most common mitochondrial uncouplers (proton translocators) have been prepared that sense the reactive oxygen species (ROS) hydrogen peroxide to release the uncouplers 2,4-dinitrophenol (DNP) and carbonylcyanide p-trifluoromethoxyphenylhydrazone (FCCP) from caged states with second order rate constants of 10 (+/- 0.8) M(-1) s(-1) and 64.8 (+/- 0.6) M(-1) s(-1), respectively. The trigger mechanism involves conversion of an arylboronate into a phenol followed by fragmentation. Hydrogen peroxide-activated uncouplers may be useful for studying the biological process of ageing. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.01.103

文献信息

• Caged mitochondrial uncouplers that are released in response to hydrogen peroxide
  作者：Caroline Quin、Linsey Robertson、Stephen J. McQuaker、Nicholas C. Price、Martin D. Brand、Richard C. Hartley

  DOI：10.1016/j.tet.2010.01.103

  日期：2010.3

  Caged versions of the most common mitochondrial uncouplers (proton translocators) have been prepared that sense the reactive oxygen species (ROS) hydrogen peroxide to release the uncouplers 2,4-dinitrophenol (DNP) and carbonylcyanide p-trifluoromethoxyphenylhydrazone (FCCP) from caged states with second order rate constants of 10 (+/- 0.8) M(-1) s(-1) and 64.8 (+/- 0.6) M(-1) s(-1), respectively. The trigger mechanism involves conversion of an arylboronate into a phenol followed by fragmentation. Hydrogen peroxide-activated uncouplers may be useful for studying the biological process of ageing. (C) 2010 Elsevier Ltd. All rights reserved.