9-diethylphosphono-10-methylacridane | 19656-30-5

• 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-diethylphosphono-10-methylacridane
• 英文别名: 9-(diethylphosphono)-N-methylacridan；diethyl 10-methyl-9,10-dihydroacridine-9-phosphonate；diethyl (10-methyl-9,10-dihydroacridin-9-yl)phosphonate；9-diethoxyphosphinyl-10-methylacridan；(10-methyl-9,10-dihydro-acridin-9-yl)-phosphonic acid diethyl ester；10-Methyl-9,10-dihydro-acridin-9-phosphonsaeurediethylester；9-diethylphosphono-10-methylacridan；9-diethoxyphosphoryl-10-methyl-9H-acridine
• CAS: 19656-30-5
• 化学式: C₁₈H₂₂NO₃P
• 分子量: 331.351
• InChiKey: ZEUASYZHMWRRMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-diethylphosphono-10-methylacridane 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：

  吖啶 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 10.0h， 生成 9-diethylphosphono-10-methylacridane
  参考文献：
  名称：

  Exogenous-oxidant-free electrochemical oxidative C–H phosphonylation with hydrogen evolution

  摘要：

  我们在此报告一种通用且环境友好的电化学氧化C-H磷酰化协议。

  DOI：

  10.1039/c9cc00975b

文献信息

• Preparation, Properties, and X-ray Structures of Bis(10-methyl-9-methyleneacridan)-type Electron Donors with a Thiophene, Bithiophene, or Terthiophene Skeleton: Redox Switching of Thiophene–Thienoquinoid Structure Accompanied by UV–vis–NIR Electrochromic Response
  作者：Takanori Suzuki、Yuuki Hoshiyama、Kazuhisa Wada、Yusuke Ishigaki、Youhei Miura、Hidetoshi Kawai、Ryo Katoono、Kenshu Fujiwara、Takanori Fukushima

  DOI：10.1246/cl.130401

  日期：2013.9.5

  The newly designed title dyes 1–3 have a thiophene-type π-skeleton, to which two methyleneacridan subunits are attached as electron-donating end groups. They undergo reversible one-wave 2e-oxidation to the corresponding dications containing a thienoquinoid moiety. The redox and spectral properties can be modified by changing the π-skeleton, and bithiophene 2 and terthiophene 3 can serve as new entries of UV–vis–NIR electrochromic materials.

  新设计的染料1至3含有噻吩型π骨架，该骨架上附有两个甲基咔啉亚单元作为电子供体末端基团。它们可经历可逆的一波2电子氧化，生成含噻吩醌型部分的二阳离子。通过改变π骨架，可以调整其氧化还原和光谱特性，而双噻吩2和三噻吩3则可作为紫外-可见-近红外电致变色材料的新成员。
• Electrochemical Oxidative Aromatizationof 9-Substituted 9,10-Dihydroacridines: Cleavage of C–H vs C–X Bond
  作者：Oleg N. Chupakhin、Alexander V. Shchepochkin、Valery N. Charushin、Anna V. Maiorova、Tatyana V. Kulikova、Konstantin Yu. Shunyaev、Andrey N. Enyashin、Pavel A. Slepukhin、Anna I. Suvorova

  DOI：10.1007/s10593-019-02562-x

  日期：2019.10

  Reactivity of dihydroacridines bearing a С–X fragment at the geminal C-9 atom (where X = C, N, O, P, S) on anode has been investigated by means of electrochemical oxidation and thermodynamic and quantum-chemical calculations. The electrochemical oxidation results either in the formation of the 9-substituted acridines or in the cleavage of the C–X bond. This dual behavior of dihydroazines is analogous

  通过电化学氧化，热力学和量子化学计算，研究了在双子C-9原子上带有С–X片段（其中X = C，N，O，P，S）的二氢anode啶的反应性。电化学氧化导致9-取代a啶的形成或C–X键的断裂。二氢嗪的这种双重行为类似于文献报道的在用化学氧化剂处理后发生的过程。
• Chemiluminescence in Autoxidation of Phosphonate Carbanions. Phospha-1,2-dioxetanes as the Most Likely High-Energy Intermediates
  作者：Jiro Motoyoshiya、Tsuneaki Ikeda、Shuji Tsuboi、Tatsuya Kusaura、Yoshino Takeuchi、Satoko Hayashi、Sachiko Yoshioka、Yutaka Takaguchi、Hiromu Aoyama

  DOI：10.1021/jo030046l

  日期：2003.7.1

  Autoxidation of the phosphonate carbanions derived from 9-phosphono-10-hydroacridanes provided chemiluminescence ascribed to the excited acridone anion. The intramolecular CIEEL (chemically initiated electron exchange luminescence) mechanism can be applied to this chemiluminescence because of the much higher emission efficiency compared to that of 9-phosphono-10-methylacridanes. The effect of the phosphonate

  衍生自9-膦酰基-10-氢rid啶烷的膦酸酯碳负离子的自氧化作用提供了归因于激发的a啶酮阴离子的化学发光。分子内CIEEL（化学引发的电子交换发光）机制可以应用于这种化学发光，因为与9-膦酰基-10-甲基ac啶相比，其发射效率要高得多。膦酸酯取代基对发光效率的影响，特别是对化学发光衰减速率的影响，可以解释为源自磷原子的化合价偏差，这与取代基对烯烃的烯化反应中几何选择性的影响有关。膦酸碳负离子。在二乙基二苯基甲基膦酸酯和芴基膦酸酯的碳负离子的自氧化中，还检测到在存在荧光团的情况下增强的化学发光。尽管证据是间接的，但这些结果强烈支持以下观点，即1,2-二氧杂环丁烷是最有可能产生激发分子的高能中间体。
• Experimental Evidence of the Occurrence of Intramolecular Electron Transfer in Catalyzed 1,2-Dioxetane Decomposition
  作者：Luiz Francisco M. L. Ciscato、Fernando H. Bartoloni、Dieter Weiss、Rainer Beckert、Wilhelm J. Baader

  DOI：10.1021/jo1013405

  日期：2010.10.1

  intramolecular chemically initiated electron exchange luminescence (CIEEL) mechanism. Emission quantum yield behavior can also be rationalized on the basis of the intramolecular CIEEL mechanism, additionally evidencing its occurrence in this transformation. Both relations constitute the first experimental evidence for the occurrence of the postulated intramolecular electron transfer in the catalyzed and induced

  利用原位光敏的1,2-二氧杂环丁烷生成并观察其热分解动力学，确定了13个带有芳族基团的cri啶取代的1,2-二氧杂环丁烷的热分解活化参数，并估算了其化学发光发射量子产率。 ，而没有分离出这些高度不稳定的环状过氧化物。分解速率常数显示了吸电子取代基的线性自由能相关性，Hammett反应常数为ρ= 1.3±0.1，这表明分子内电子从a啶部分转移到1,2-二氧杂环丁烷环上已发生通过分子内化学引发的电子交换发光（CIEEL）机制。发射量子产率行为也可以基于分子内CIEEL机理进行合理化，另外证明其在这种转变中的发生。这两种关系构成了在适当取代的1,2-二氧杂环丁烷催化和诱导的分解中假定的分子内电子转移发生的第一个实验证据。
• Study on second harmonic generation of 9-benzylidene-substituted-10-methyl-9,10-dihydroacridines
  作者：Hua-Can Song、Rui-Jiang Jin、Xiang-Li Zheng、Bai-Ning Ying

  DOI：10.1016/s1386-1425(01)00461-9

  日期：2001.12

  Eight 9-benzylidene-substituted-10-methyl-9,10-dihydroacridine derivatives were synthesized from acridine as starting material and were characterized by H-1-NMR, C-13-NMR, Ms and elemental analysis. The second harmonic generation (SHG) values of these compounds were determined in powder using Nd:YAG as a laser source, as compared with urea powder, and the values of second-order polarizabilities the values of the composite magnitude (beta (CT mug)) of molecular hypersusceptibilities and their moment of these compounds were obtained by the solvatochromic method under ground state for everyone. The results showed that SHG value of 10 is higher than that of urea, the beta (CT mug) of 5 (107.8 x 10(-30) esu) is lower than that of 4-nitro-N,N-dimethylaniline (30 x 10(-30) esu); the beta (CT mug) of 7 (350.8 x 10(-30) esu) and 10 (244.6 x 10(-30) esu) are higher than that of 4-nitro-N,N-dimethylaniline; the beta (CT mug) of 8 (3553 x 10(-30) esu), 11 (1187 x 10(-30) esu) and 12 (1163 x 10(-30) esu) are much more higher than that of 4-nitro-N,N-dimethylaniline. The results demonstrated that this series of compounds possesses good second-order nonlinear optical (NLO) property. The regular relationship could not be obtained between electronegativity of substituents (R) attached to benzylidene ring and SHG values or beta (CT mug) values although the Rs are different in electronegativity and should make an effect on the extent of intramolecular electron-transfer and would consequently influence SHG or beta (CT mug). The electron-withdrawing ability of R from benzylidene ring played an important role on lambda (max) of these compounds. (C) 2001 Elsevier Science BN. All rights reserved.