9-phenyl-10-methylacridinyl radical | 100667-92-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 9-phenyl-10-methylacridinyl radical
• 英文别名: N-methyl-9-phenylacridanyl radical
• CAS: 100667-92-3
• 化学式: C₂₀H₁₆N
• 分子量: 270.354
• InChiKey: XYZWSDDCGHKALB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  9-苯基吖啶 在 silver(I) chloride 作用下， 以 乙醚 、 水 为溶剂， 生成 9-phenyl-10-methylacridinyl radical
  参考文献：
  名称：

  Koper, N. W.; Jonker, S. A.; Verhoeven, J. W., Recueil des Travaux Chimiques des Pays-Bas, 1985, vol. 104, # 11, p. 296 - 301

  摘要：

  DOI：

文献信息

• Photoalkylation of 10-Alkylacridinium Ion via a Charge-Shift Type of Photoinduced Electron Transfer Controlled by Solvent Polarity
  作者：Shunichi Fukuzumi、Kei Ohkubo、Tomoyoshi Suenobu、Kouta Kato、Mamoru Fujitsuka、Osamu Ito

  DOI：10.1021/ja004311l

  日期：2001.9.1

  (DeAcrH+) in a nonpolar solvent (benzene) is found to be as efficient as those of 10-methylacridinium cation (MeAcrH+) and DeAcrH+ in a polar solvent (acetonitrile). Irradiation of the absorption bands of MeAcrH+ in acetonitrile solution containing tetraalkyltin compounds (R(4)Sn) results in the efficient and selective reduction of MeAcrH+ to yield the 10-methyl-9-alkyl-9,10-dihydroacridine (AcrHR)

  发现在非极性溶剂（苯）中，从各种电子供体到 10-癸吖啶鎓阳离子 (DeAcrH+) 的单线激发态的光致电子转移反应与 10-甲基吖啶鎓阳离子 (MeAcrH+ ) 和 DeAcrH+ 在极性溶剂（乙腈）中。在含有四烷基锡化合物 (R(4)Sn) 的乙腈溶液中，对 MeAcrH+ 的吸收带进行辐照会导致 MeAcrH+ 的有效和选择性还原，从而产生 10-甲基-9-烷基-9,10-二氢吖啶 (AcrHR)。当 MeAcrH+ 被可溶于苯的 DeAcrH+ 取代时，在苯中会发生相同类型的反应。使用 4-叔丁基-1-苄基-1,4-二氢烟酰胺 (Bu(t)BNAH) 代替 R(4)Sn，R'AcrH+（R' = Me 和 De）的光烷基化也在乙腈和苯中进行, 产生 MeAcrHBu(t)。量子产率测定、电子供体对 R'AcrH+ 的荧光猝灭以及通过激光闪光光解实验直接检测反应中间体表明，R'AcrH+
• Hydride Transfer from 9-Substituted 10-Methyl-9,10-dihydroacridines to Hydride Acceptors via Charge-Transfer Complexes and Sequential Electron−Proton−Electron Transfer. A Negative Temperature Dependence of the Rates
  作者：Shunichi Fukuzumi、Kei Ohkubo、Yoshihiro Tokuda、Tomoyoshi Suenobu

  DOI：10.1021/ja9941375

  日期：2000.5.1

  attributed mainly to that of proton transfer from AcrHR•+ to A•- following the initial electron transfer from AcrHR to A. The overall hydride transfer reaction from AcrHR to A therefore proceeds via sequential electron−proton−electron transfer in which the initial electron transfer to give the radical ion pair (AcrHR•+ A•-) is in equilibrium and the proton transfer from AcrHR•+ to A•- is the rate-determining

  9-取代的 10-甲基-9,10-二氢吖啶 (AcrHR) 在与氢化物受体 (A) 如乙腈中的对苯醌衍生物和四氰基乙烯 (TCNE) 的反应中的反应性变化很大，从 R 开始，范围为 107 = H 到 But 和 CMe2COOMe。将氢化物转移反应的反应性变化与独立测定的自由基阳离子 (AcrHR•+) 的去质子化反应性的较大变化进行比较表明，反应性的较大变化主要归因于质子从 AcrHR•+ 转移到A•- 在从 AcrHR 到 A 的初始电子转移之后。因此，从 AcrHR 到 A 的整个氢化物转移反应是通过顺序电子-质子-电子转移进行的，其中产生自由基离子对 (AcrHR•+ A•-) 的初始电子转移处于平衡状态，而来自 AcrHR•+ 的质子转移到 A•- 是速率决定步骤。电荷转移复合物显示在氢化物转移过程中形成...
• Nucleophilic addition versus electron transfer in carbonylmetallate salts. Donor-acceptor interactions in the precursor ion pairs
  作者：T. Michael Bockman、Jay K. Kochi

  DOI：10.1002/(sici)1099-1395(199707)10:7<542::aid-poc918>3.0.co;2-o

  日期：1997.7
• Steric and Kinetic Isotope Effects in the Deprotonation of Cation Radicals of NADH Synthetic Analogs
  作者：Agnes Anne、Sylvie Fraoua、Philippe Hapiot、Jacques Moiroux、Jean-Michel Saveant

  DOI：10.1021/ja00133a014

  日期：1995.7

  The deprotonation rate constants and kinetic isotope effects of the cation radicals have been determined by combined use of direct electrochemical techniques at micro- and ultramicroelectrodes, redox catalysis, and laser flash photolysis, over a extended series of opposing bases. Significant steric hindrance to deprotonation results from encumbering of the opposing base and of the functional carbon in the cation radical by alkyl groups. Kinetic isotope effects, ranging from 2 to 12 in terms of k(H)/k(D), appear upon substituting H to D at the functional carbon of the cation radical. The modest magnitude of the kinetic isotope effects and the fact that they are insensitive to steric hindrance show that proton (or H-atom) tunneling does not interfere significantly in the deprotonation reaction. All the cation radicals in the methylacridan series are strong acids, with pK(a)'s ranging from 0.8 to 1.7, as determined from thermodynamic cycles involving measured standard potentials and hydride-transfer equilibrium constants.
• Becker, H. G. O.; Kohrs, K., Journal fur praktische Chemie (Leipzig 1954), 1990, vol. 332, # 5, p. 651 - 657
  作者：Becker, H. G. O.、Kohrs, K.

  DOI：——

  日期：——