(E)-3-(10-methyl-9-anthryl)-1-(pyrid-2'-yl)prop-2-enone | 915233-83-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(10-methyl-9-anthryl)-1-(pyrid-2'-yl)prop-2-enone
• CAS: 915233-83-9
• 化学式: C₂₃H₁₇NO
• 分子量: 323.394
• InChiKey: AGGRIKXKRNVKCX-BUHFOSPRSA-N

物化性质

• 沸点：
  558.2±42.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.59
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  29.96
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-3-(10-methyl-9-anthryl)-1-(pyrid-2'-yl)prop-2-enone 在 氯化亚砜 、 硫酸 、 potassium tert-butylate 、 ammonium acetate 、 水 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 88.0h， 生成 dimethyl-4'-(10-methyl-9-anthryl)-2,2':6'2''-terpyridine-6,6''-dicarboxylate
  参考文献：
  名称：

  A Europium(III) Complex as an Efficient Singlet Oxygen Luminescence Probe

  摘要：

  A new europium(III) complex, [4'-(10-methyl-9-anthryl)-2,2': 6', 2"-terpyridine-6,6"-diyl] bis(methylenenitrilo) tetrakis(acetate)-Eu3+, was designed and synthesized as a highly sensitive and selective time-gated luminescence probe for singlet oxygen (O-1(2)). The new probe is highly water soluble with a large stability constant of similar to 10(21) and a wide pH available range (pH 3-10), and can specifically react with O-1(2) to form its endoperoxide (EP-MTTA-Eu3+) with a high reaction rate constant at 10(10) M-1 s(-1), accompanied by the remarkable increases of luminescence quantum yield from 0.90% to 13.8% and lifetime from 0.80 to 1.29 ms, respectively. The wide applicability of the probe was demonstrated by detection of O-1(2) generated from a MoO42-/H2O2 system, a photosensitization system of 5,10,15,20-tetrakis(1-methyl-4-pyridinio)-porphyrin tetra(p-toluenesulfonate) (TMPyP), and a horseradish peroxidase catalyzed aerobic oxidation system of indole-3-acetic acid (IAA). In addition, it was found that the new probe could be easily transferred into living HeLa cells by incubation with TMPyP. A time-gated luminescence imaging technique that can fully eliminate the short-lived background fluorescence from TMPyP and cell components has been successfully developed for monitoring the time-dependent generation of O-1(2) in living cells.

  DOI：

  10.1021/ja062990f
• 作为产物：
  描述：

  2-乙酰基吡啶 、 10-甲基蒽-9-甲醛 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以81.6%的产率得到(E)-3-(10-methyl-9-anthryl)-1-(pyrid-2'-yl)prop-2-enone
  参考文献：
  名称：

  A Europium(III) Complex as an Efficient Singlet Oxygen Luminescence Probe

  摘要：

  A new europium(III) complex, [4'-(10-methyl-9-anthryl)-2,2': 6', 2"-terpyridine-6,6"-diyl] bis(methylenenitrilo) tetrakis(acetate)-Eu3+, was designed and synthesized as a highly sensitive and selective time-gated luminescence probe for singlet oxygen (O-1(2)). The new probe is highly water soluble with a large stability constant of similar to 10(21) and a wide pH available range (pH 3-10), and can specifically react with O-1(2) to form its endoperoxide (EP-MTTA-Eu3+) with a high reaction rate constant at 10(10) M-1 s(-1), accompanied by the remarkable increases of luminescence quantum yield from 0.90% to 13.8% and lifetime from 0.80 to 1.29 ms, respectively. The wide applicability of the probe was demonstrated by detection of O-1(2) generated from a MoO42-/H2O2 system, a photosensitization system of 5,10,15,20-tetrakis(1-methyl-4-pyridinio)-porphyrin tetra(p-toluenesulfonate) (TMPyP), and a horseradish peroxidase catalyzed aerobic oxidation system of indole-3-acetic acid (IAA). In addition, it was found that the new probe could be easily transferred into living HeLa cells by incubation with TMPyP. A time-gated luminescence imaging technique that can fully eliminate the short-lived background fluorescence from TMPyP and cell components has been successfully developed for monitoring the time-dependent generation of O-1(2) in living cells.

  DOI：

  10.1021/ja062990f