2,3,6,7-tetramethyl-9-(tricyclo[3.3.1.1^3,7]dec-2-ylidene)-10(9H)-acridineacetic acid ethyl ester | 1481751-26-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,6,7-tetramethyl-9-(tricyclo[3.3.1.1^3,7]dec-2-ylidene)-10(9H)-acridineacetic acid ethyl ester
• CAS: 1481751-26-1
• 化学式: C₃₁H₃₇NO₂
• 分子量: 455.64
• InChiKey: AJRMTEMRIGCJDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.19
• 重原子数：
  34.0
• 可旋转键数：
  3.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,3,6,7-tetramethyl-9-(tricyclo[3.3.1.1^3,7]dec-2-ylidene)-10(9H)-acridineacetic acid ethyl ester 在 氧气 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以84%的产率得到dispiro[2,3,6,7-tetramethylacridine-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
• 作为产物：
  描述：

  2-((3,4-dimethylphenyl)amino)-4,5-dimethylbenzoic acid 在 lithium aluminium tetrahydride 、 TiCl₃(THF)₃ 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 45.0h， 生成 2,3,6,7-tetramethyl-9-(tricyclo[3.3.1.1^3,7]dec-2-ylidene)-10(9H)-acridineacetic 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