Acridin-9-yl-phosphonic acid diisopropyl ester | 675850-18-7

• 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: Acridin-9-yl-phosphonic acid diisopropyl ester
• 英文别名: 9-Di(propan-2-yloxy)phosphorylacridine
• CAS: 675850-18-7
• 化学式: C₁₉H₂₂NO₃P
• 分子量: 343.362
• InChiKey: AODAPDHDABHUIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Acridin-9-yl-phosphonic acid diisopropyl ester 在 hydroxide 、 双氧水 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 acridone anion
  参考文献：
  名称：

  Reactions of 9-Phosphorylacridines with Aqueous Hydrogen Peroxide Accompanied by Weak Chemilumine-scence: Remarkable Substituent Effect on Emission Efficiency

  摘要：

  The reaction of 9-phosphorylacridines with aqueous hydrogen peroxide provides weak chemiluminescence, whose emission efficiency depends on the structures of the phosphorus groups. The bulky substituents in the phosphorus groups increased the chemiluminescence quantum yields, which can be explained by assuming that the present chemiluminescence reaction involves a CIEEL process via phospha-1,2-dioxetanes as the high-energy intermediates.

  DOI：

  10.3987/com-03-9871
• 作为产物：
  描述：

  三异丙基亚磷酸酯 在 四氯苯醌 作用下， 生成 Acridin-9-yl-phosphonic acid diisopropyl ester
  参考文献：
  名称：

  Reactions of 9-Phosphorylacridines with Aqueous Hydrogen Peroxide Accompanied by Weak Chemilumine-scence: Remarkable Substituent Effect on Emission Efficiency

  摘要：

  The reaction of 9-phosphorylacridines with aqueous hydrogen peroxide provides weak chemiluminescence, whose emission efficiency depends on the structures of the phosphorus groups. The bulky substituents in the phosphorus groups increased the chemiluminescence quantum yields, which can be explained by assuming that the present chemiluminescence reaction involves a CIEEL process via phospha-1,2-dioxetanes as the high-energy intermediates.

  DOI：

  10.3987/com-03-9871

文献信息

• EPR-electrochemical monitoring of P–C coupling: Towards one-step electrochemical phosphorylation of acridine
  作者：Tatyana V. Gryaznova、Elizaveta O. Nikanshina、Robert R. Fayzullin、Daut R. Islamov、Maxim V. Tarasov、Kirill V. Kholin、Yulia H. Budnikova

  DOI：10.1016/j.electacta.2022.140946

  日期：2022.10

  was investigated by voltammetry and electron paramagnetic resonance (EPR) spectroscopy methods. The reaction intermediates, such as dihydroacridine dialkylphosphonates, have been isolated, proven, and investigated by voltammetry, X-ray diffraction, etc. The magnetic resonance parameters of intermediates, the radical cations of triorganyl phosphites captured by a spin trap PBN, acridine, as well as phosphorylated

  一种温和、高效的位点选择性直接 C(sp 2 ) 电化学方法)– 已开发出用亚磷酸三有机酯对吖啶进行 H 磷酸化。无催化剂、无外部氧化剂和无金属的联合电合成以良好的收率导致选择性 C9 磷酸化。通过伏安法和电子顺磁共振 (EPR) 光谱法研究了这些一锅氧化转化的机制。反应中间体，如二氢吖啶二烷基膦酸酯，已通过伏安法、X 射线衍射等方法分离、证明和研究。中间体的磁共振参数、自旋阱 PBN 捕获的亚磷酸三有机酯自由基阳离子、吖啶，以及磷酸化吖啶衍生物，已被确定。