9-(1-naphthylmethyl)-10-methyl-9,10-dihydroacridine | 138616-15-6

• 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-(1-naphthylmethyl)-10-methyl-9,10-dihydroacridine
• 英文别名: 10-methyl-9-(naphthalen-1-ylmethyl)-9H-acridine
• CAS: 138616-15-6
• 化学式: C₂₅H₂₁N
• 分子量: 335.448
• InChiKey: FWSUKTJVFCNURP-UHFFFAOYSA-N

物化性质

• 沸点：
  500.2±30.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-(1-naphthylmethyl)-10-methyl-9,10-dihydroacridine 在 高氯酸 作用下， 以 水 、 乙腈 为溶剂， 反应 40.0h， 以86%的产率得到甲基萘
  参考文献：
  名称：

  Photoinduced Cleavage of the C–C Bonds of 9-Alkyl-10-methyl-9,10-dihydroacridines by Perchloric Acid

  摘要：

  9-烷基-10-甲基-9,10-二氢吖啶的C-C单键[AcrHR：R = 1-萘基甲基、二苯基甲基和AcrH（二聚体）]在二氯甲烷中受到过氯酸的处理，并在AcrHR的吸收带照射下容易被裂解，生成相应的烷烃（RH）和10-甲基吖啶铵离子（AcrH+）。

  DOI：

  10.1246/cl.1991.1905
• 作为产物：
  描述：

  1-萘乙酸 、 10-甲基吖啶高氯酸盐 在 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 生成 9-(1-naphthylmethyl)-10-methyl-9,10-dihydroacridine
  参考文献：
  名称：

  Fukuzumi, Shonichi; Tokuda, Yoshihiro; Kitano, Toshiaki, Journal of the American Chemical Society, 1993, vol. 115, # 20, p. 8960 - 8968

  摘要：

  DOI：

文献信息

• Photoinduced cleavage of the carbon-carbon bond of 9-(1-naphthylmethyl)-10-methyl-9,10-dihydroacridines by perchloric acid via intramolecular electron-transfer excitation
  作者：Shunichi Fukuzumi、Yoshihiro Tokuda、Morifumi Fujita

  DOI：10.1021/j100200a038

  日期：1992.10

  The C(9)-C bond of 9-(1-naphthylmethyl)-10-methyl-9, 10-dihydroacridine (AcrHR) is readily cleaved by HClO4 in acetonitrile (MeCN) under irradiation of the absorption band of AcrHR to yield RH and AcrH+. The dependence of the fluorescence maximum on solvent dielectric constant indicates a highly polar singlet excited state with the dipole moment of ca. 15.6 D, while the fluorescence maximum of 9,10-dihydro-10-methylacridine (AcrH2) is insensitive to the solvent. The fluorescence of AcrHR is efficiently quenched by HClO4 with the rate constant of 8.6 X 10(9) M-1 s-1 in MeCN at 298 K. The same quenching rate constant has been obtained from the dependence of the quantum yields on [HClO4] for the photoinduced cleavage of the C-C bond of AcrHR by HClO4 in MeCN at 298 K. Thus, the photoinduced intramolecular charge transfer from the acridine moiety to the naphthalene moiety in AcrHR results in the generation of the highly polarized C-C bond which is susceptible to the cleavage by HClO4. The C(9)-C bond of AcrHR is also cleaved upon the intermolecular electron-transfer oxidation of AcrHR by Fe(ClO4)3 and Fe(phen)33+ (phen = 1,10-phenanthroline) in MeCN to yield AcrH+ while the C(9)-H bond is cleaved in the case of AcrH2.