(3-bromo-5-cyanomethyl-2,4,6-trimethylphenyl)acetonitrile | 917486-38-5

• 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: (3-bromo-5-cyanomethyl-2,4,6-trimethylphenyl)acetonitrile
• 英文别名: 5-Bromo-2,4,6-trimethyl-1,3-benzenediacetonitrile；2-[3-bromo-5-(cyanomethyl)-2,4,6-trimethylphenyl]acetonitrile
• CAS: 917486-38-5
• 化学式: C₁₃H₁₃BrN₂
• 分子量: 277.164
• InChiKey: JSXBFGIZABKSAK-UHFFFAOYSA-N

物化性质

• 熔点：
  185 °C
• 沸点：
  435.3±40.0 °C(Predicted)
• 密度：
  1.339±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3-bromo-5-cyanomethyl-2,4,6-trimethylphenyl)acetonitrile 在 四(三苯基膦)钯 potassium phosphate 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 (5-cyanomethyl-2'-hydroxy-2,4,6-trimethylbiphenyl-3-yl)acetonitrile
  参考文献：
  名称：

  Phenol-containing bis(oxazolines): synthesis and fluorescence sensing of amines

  摘要：

  The fluorescence sensing of primary amines as their neutral forms has been studied with bis(oxazolinyl)phenols (Me-BOP, Ph-BOP), which are efficiently synthesized starting from mesitylene in six steps and in overall 12-22% yields. The BOP sensors showed fluorescence enhancement toward butylamine and several arylethylamines, whereas they showed fluorescence quenching toward secondary and branched amines. The opposite fluorescence behavior is explained by an increased conformational restriction at the excited state, at which a proton transfer complex between the host and guest forms that is stabilized in a tripodal hydrogen bonding mode. This is the first example in which fluorescence enhancement is observed in amine sensing with phenolic fluorophores. Enantiomeric alpha-chiral organoamines were also sensed with different fluorescent intensity changes by Ph-BOP, complementing the previous tris(oxazolines) that sense enantiomeric alpha-chiral organoammonium ions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.060
• 作为产物：
  描述：

  2,4-二(溴甲基)-1,3,5-三甲基苯 在 溶剂黄146 、 benzyltrimethylazanium tribroman-2-uide 、 zinc(II) chloride 作用下， 以 甲醇 、 水 为溶剂， 反应 10.0h， 生成 (3-bromo-5-cyanomethyl-2,4,6-trimethylphenyl)acetonitrile
  参考文献：
  名称：

  Phenol-containing bis(oxazolines): synthesis and fluorescence sensing of amines

  摘要：

  The fluorescence sensing of primary amines as their neutral forms has been studied with bis(oxazolinyl)phenols (Me-BOP, Ph-BOP), which are efficiently synthesized starting from mesitylene in six steps and in overall 12-22% yields. The BOP sensors showed fluorescence enhancement toward butylamine and several arylethylamines, whereas they showed fluorescence quenching toward secondary and branched amines. The opposite fluorescence behavior is explained by an increased conformational restriction at the excited state, at which a proton transfer complex between the host and guest forms that is stabilized in a tripodal hydrogen bonding mode. This is the first example in which fluorescence enhancement is observed in amine sensing with phenolic fluorophores. Enantiomeric alpha-chiral organoamines were also sensed with different fluorescent intensity changes by Ph-BOP, complementing the previous tris(oxazolines) that sense enantiomeric alpha-chiral organoammonium ions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.060

文献信息

• Phenol-containing bis(oxazolines): synthesis and fluorescence sensing of amines
  作者：Yun Mi Chung、Balamurali Raman、Kyo Han Ahn

  DOI：10.1016/j.tet.2006.09.060

  日期：2006.12

  The fluorescence sensing of primary amines as their neutral forms has been studied with bis(oxazolinyl)phenols (Me-BOP, Ph-BOP), which are efficiently synthesized starting from mesitylene in six steps and in overall 12-22% yields. The BOP sensors showed fluorescence enhancement toward butylamine and several arylethylamines, whereas they showed fluorescence quenching toward secondary and branched amines. The opposite fluorescence behavior is explained by an increased conformational restriction at the excited state, at which a proton transfer complex between the host and guest forms that is stabilized in a tripodal hydrogen bonding mode. This is the first example in which fluorescence enhancement is observed in amine sensing with phenolic fluorophores. Enantiomeric alpha-chiral organoamines were also sensed with different fluorescent intensity changes by Ph-BOP, complementing the previous tris(oxazolines) that sense enantiomeric alpha-chiral organoammonium ions. (c) 2006 Elsevier Ltd. All rights reserved.