dispiro[2,7-dimethylacridine-9(10H),3′-[1,2]dioxetane-4′,2″-tricyclo[3.3.1.1^3,7]decane]-10-acetic acid ethyl ester | 1481751-01-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: dispiro[2,7-dimethylacridine-9(10H),3′-[1,2]dioxetane-4′,2″-tricyclo[3.3.1.1^3,7]decane]-10-acetic acid ethyl ester
• CAS: 1481751-01-2
• 化学式: C₂₉H₃₃NO₄
• 分子量: 459.585
• InChiKey: YPEVGGPOFZPDHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,7-dimethylacridin-9(10H)-one 在 lithium aluminium tetrahydride 、 TiCl₃(THF)₃ 、 氧气 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 dispiro[2,7-dimethylacridine-9(10H),3′-[1,2]dioxetane-4′,2″-tricyclo[3.3.1.1^3,7]decane]-10-acetic acid ethyl ester
  参考文献：
  名称：

  Preparation and Characterization of Thermochemiluminescent Acridine-Containing 1,2-Dioxetanes as Promising Ultrasensitive Labels in Bioanalysis

  摘要：

  Thermochemiluminescence is the luminescence process in which a thermodynamically unstable molecule decomposes with light emission when heated above a threshold temperature. We recently reported the thermochemiluminescence properties of an acridine-containing 1,2-dioxetane, which emits at relatively low temperatures (i.e., below 100 degrees C). Herein, we explored the effect of the introduction of methyl substituents in the acridine system. The methyl group did not determine an excessive destabilization of 1,2-dioxetane ring nor significantly affect the general physical properties of the molecule. Monosubstituted methyl derivatives and a series of derivatives bearing several combinations of two, three, and four methyl groups were prepared. The rate of formation of 1,2-dioxetane derivatives 1b-k strongly depended on the methyl substitution pattern. All members of this library of mono-, di-, tri-, and tetramethyl-substituted derivatives were characterized in terms of photophysical and thermochemiluminescence properties. The introduction of methyl groups into the acridine ring caused a marked decrease in the activation energy of the thermochemiluminescent reaction. Tri- and tetramethyl-substituted acridones had the highest fluorescence quantum yields, in the range 0.48-0.52, and the corresponding 1,2-dioxetanes 1h and 1j showed in thermochemiluminescence imaging experiments limit of detection values more than ten times lower with respect to the unsubstituted derivative.

  DOI：

  10.1021/jo401683r

文献信息

• Preparation and Characterization of Thermochemiluminescent Acridine-Containing 1,2-Dioxetanes as Promising Ultrasensitive Labels in Bioanalysis
  作者：Massimo Di Fusco、Arianna Quintavalla、Claudio Trombini、Marco Lombardo、Aldo Roda、Massimo Guardigli、Mara Mirasoli

  DOI：10.1021/jo401683r

  日期：2013.11.15

  Thermochemiluminescence is the luminescence process in which a thermodynamically unstable molecule decomposes with light emission when heated above a threshold temperature. We recently reported the thermochemiluminescence properties of an acridine-containing 1,2-dioxetane, which emits at relatively low temperatures (i.e., below 100 degrees C). Herein, we explored the effect of the introduction of methyl substituents in the acridine system. The methyl group did not determine an excessive destabilization of 1,2-dioxetane ring nor significantly affect the general physical properties of the molecule. Monosubstituted methyl derivatives and a series of derivatives bearing several combinations of two, three, and four methyl groups were prepared. The rate of formation of 1,2-dioxetane derivatives 1b-k strongly depended on the methyl substitution pattern. All members of this library of mono-, di-, tri-, and tetramethyl-substituted derivatives were characterized in terms of photophysical and thermochemiluminescence properties. The introduction of methyl groups into the acridine ring caused a marked decrease in the activation energy of the thermochemiluminescent reaction. Tri- and tetramethyl-substituted acridones had the highest fluorescence quantum yields, in the range 0.48-0.52, and the corresponding 1,2-dioxetanes 1h and 1j showed in thermochemiluminescence imaging experiments limit of detection values more than ten times lower with respect to the unsubstituted derivative.