9-(m-nitrobenzylidene)-10-methyl-9,10-dihydroacridine | 19656-34-9

• 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-(m-nitrobenzylidene)-10-methyl-9,10-dihydroacridine
• 英文别名: 9-(m-nitro)benzylidene-9,10-dihydro-10-methylacridine；9-[(3-nitrophenyl)methylidene]-10-methyl-9,10-dihydroacridine；10-Methyl-9-[(3-nitrophenyl)methylidene]acridine
• CAS: 19656-34-9
• 化学式: C₂₁H₁₆N₂O₂
• 分子量: 328.37
• InChiKey: PRDJJDAPRLEFJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-(m-nitrobenzylidene)-10-methyl-9,10-dihydroacridine 在 氧气 、 亚甲兰 作用下， 以 乙腈 为溶剂， 反应 0.03h， 生成 10-Methyl-4'-(3-nitrophenyl)spiro[acridine-9,3'-dioxetane]
  参考文献：
  名称：

  催化的1,2-二氧杂环丁烷分解中发生分子内电子转移的实验证据

  摘要：

  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。

  DOI：

  10.1021/jo1013405
• 作为产物：
  描述：

  9-methyl-9-azonianthracene methyl sulfate 在 正丁基锂 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 2.17h， 生成 9-(m-nitrobenzylidene)-10-methyl-9,10-dihydroacridine
  参考文献：
  名称：

  Substituent effect on the chemiluminescence quantum efficiency of some acridan derivatives

  摘要：

  DOI：

  10.1007/bf00809369

文献信息

• 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.