(9,10-dihydro-10-methyl-9-acridinyl)diphenylphosphine oxide | 145995-55-7

• 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: (9,10-dihydro-10-methyl-9-acridinyl)diphenylphosphine oxide
• 英文别名: 9-diphenylphosphoryl-10-methyl-9H-acridine
• CAS: 145995-55-7
• 化学式: C₂₆H₂₂NOP
• 分子量: 395.441
• InChiKey: BCWYZBXQYQADAK-UHFFFAOYSA-N

物化性质

• 沸点：
  532.9±49.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (9,10-dihydro-10-methyl-9-acridinyl)diphenylphosphine oxide 在 potassium tert-butylate 、 氧气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 甲基-蒽酮
  参考文献：
  名称：

  Chemiluminescent oxidation of phosphonates : Phospha-1,2-dioxetanes as possible intermediates

  摘要：

  Chemiluminescence was observed in autooxidation of the phosphonate carbanions and the related reaction, which gave a strong proof of phospha-1,2-dioxetanes as the intermediates in these reactions.

  DOI：

  10.1016/s0040-4039(00)78207-4
• 作为产物：
  描述：

  tert-butyl diphenylphosphinite 以 乙腈 为溶剂， 生成 (9,10-dihydro-10-methyl-9-acridinyl)diphenylphosphine oxide
  参考文献：
  名称：

  烷基二苯基次膦酸盐与 10-甲基吖啶鎓离子的 Arbuzov 反应。膦中间体形成与分解的动力学研究

  摘要：

  烷基二苯基次膦酸盐 (1) 与 10-甲基吖啶碘化物 (2a) 快速反应，得到相应的鏻离子 (3)，其逐渐分解为氧化膦，即预期的 Arbuzov 产物。第一步（形成鏻）和第二步（分解鏻）的速率差异很大，这使我们能够对这两个步骤进行独立的动力学研究，发现第一步服从二级动力学和一级动力学分别针对 1 和 2a。当 1 中的烷基取代基是伯或仲时，第二步根据 SN2 机制进行，其中碘离子作为亲核试剂，或者当取代基是叔时，按照 SN1 机制进行。用活化参数对第一步进行更仔细的检查表明，随着 1 中的取代基变得更大，这一步的过渡态变得更像反应物。第二步，活化参数的调查表明，碳氧键在 3 p ...

  DOI：

  10.1246/bcsj.66.2077

文献信息

• Visible light irradiated photocatalytic C(sp³)–H phosphorylation of xanthenes and 9,10-dihydroacridines with P(O)–H compounds
  作者：Mingjun Liu、Jiarui Zhu、Xuming Jiang、Xiangyun Yang、Qian Chen

  DOI：10.1039/d3ob01053h

  日期：——

  Photocatalytic C(sp3)–H phosphorylation of xanthenes and 9,10-dihydroacridines with P(O)–H compounds under the irradiation of 18 W blue LEDs at room temperature using fluorescein as the photocatalyst and molecular oxygen (O2) as the sole oxidant has been achieved. The newly developed reaction provides direct access to 9-phosphorylated xanthene derivatives with good functional group compatibility.

  以荧光素为光催化剂，分子氧 (O 2 ) 为光催化剂，室温下 18 W 蓝光 LED 照射下，氧杂蒽和 9,10-二氢吖啶与 P(O)-H 化合物的光催化 C(sp 3 )–H磷酸化已实现唯一氧化剂。新开发的反应可以直接获得具有良好官能团相容性的9-磷酸化呫吨衍生物。
• Yasui, Shinro, Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 75, # 1-4, p. 197 - 200
  作者：Yasui, Shinro

  DOI：——

  日期：——
• Reactivity of Phosphorus-Centered Radicals Generated during the Photoreaction of Diphenylphosphinous Acid with 10-Methylacridinium Salt
  作者：Shinro Yasui、Kosei Shioji、Atsuyoshi Ohno、Masakuni Yoshihara

  DOI：10.1021/jo00112a034

  日期：1995.4

  Diphenylphosphinous acid (1) reacts with 10-methylacridinium iodide (2a) in aqueous acetonitrile during irradiation by visible light under an argon atmosphere at 20 degrees C to afford diphenylphosphinic acid (3) and 10-methylacridan (4). The effects of the solvent and atmosphere and the effect of added iodide ion (I-) or iodine (I-2) on the product distribution show that the mechanism involves initial single-electron transfer (SET) from 1 to 2a in the photoexcited state, by which cation radical 1(+.) and dihydroacridinyl radical 2(.) are generated. Cation radical 1(+.) undergoes electrophilic reaction with water in the solvent, and the resulting phosphoranyl radical decomposes through SET to iodine atom (I-.) rather than undergoing beta-scission, eventually giving 3. Protonation to 2(.) followed by reduction by I- affords 4. These reaction sequences make up the catalytic I-./I- couple. The results are interpreted on the basis of reported redox potentials.
• The thermal- and photo-reactions of a diphenylphosphinite ester with 10-methylacridinium iodide. Discrimination between polar and single electron transfer processes.
  作者：Shinro Yasui、Kosei Shioji、Masakuni Yoshihara、Toshihisa Maeshima、Atsuyoshi Ohno

  DOI：10.1016/s0040-4039(00)60869-9

  日期：1992.11

  The thermal-reaction of isopropyl diphenylphosphinite with 10-methylacridinuim iodide results in the formation of a phosphonium ion through a polar process, whereas the reaction under the irradiation of light affords 10-methylacridan as well as isopropyl diphenylphosphinate through single electron transfer (SET) from the former to the latter.
• The Arbuzov Reaction of Alkyl Diphenylphosphinites with 10-Methylacridinium Ion. Kinetic Study on the Formation and the Decomposition of Phosphonium Intermediates
  作者：Shinro Yasui、Kosei Shioji、Masakuni Yoshihara、Toshihisa Maeshima、Atsuyoshi Ohno

  DOI：10.1246/bcsj.66.2077

  日期：1993.7

  Alkyl diphenylphosphinites (1) react rapidly with 10-methylacridinium iodide (2a) to afford the corresponding phosphonium ions (3), which gradually decompose to phosphine oxide, the expected Arbuzov product. Large difference in the rate of the first (phosphonium-forming) and the second (phosphonium-decomposing) steps enables us independent kinetic investigation for both steps, with which it has been

  烷基二苯基次膦酸盐 (1) 与 10-甲基吖啶碘化物 (2a) 快速反应，得到相应的鏻离子 (3)，其逐渐分解为氧化膦，即预期的 Arbuzov 产物。第一步（形成鏻）和第二步（分解鏻）的速率差异很大，这使我们能够对这两个步骤进行独立的动力学研究，发现第一步服从二级动力学和一级动力学分别针对 1 和 2a。当 1 中的烷基取代基是伯或仲时，第二步根据 SN2 机制进行，其中碘离子作为亲核试剂，或者当取代基是叔时，按照 SN1 机制进行。用活化参数对第一步进行更仔细的检查表明，随着 1 中的取代基变得更大，这一步的过渡态变得更像反应物。第二步，活化参数的调查表明，碳氧键在 3 p ...