(4aα,8aα,9aβ,10aα)-tetradecahydro-10-methylacridine | 16726-26-4

• 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: (4aα,8aα,9aβ,10aα)-tetradecahydro-10-methylacridine
• 英文别名: (4aR,8aR,9aR,10aS)-10-methyl-2,3,4,4a,5,6,7,8,8a,9,9a,10a-dodecahydro-1H-acridine
• CAS: 16726-26-4；24506-22-7；26432-23-5；30462-82-9；114544-11-5；114544-14-8
• 化学式: C₁₄H₂₅N
• 分子量: 207.359
• InChiKey: QSBOLGXNGSHMEK-SYQHCUMBSA-N

物化性质

• 沸点：
  281.9±8.0 °C(Predicted)
• 密度：
  0.936±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (4aα,8aα,9aβ,10aα)-tetradecahydro-10-methylacridine 在 potassium chromate 、 双氧水 作用下， 以 水 为溶剂， 反应 3.0h， 生成 trans-anti-cis-perhydroacridine
  参考文献：
  名称：

  Potmischil, Francisc; Dobrinescu, Claudiu; Nicolescu, Alina, Revue Roumaine de Chimie, 2012, vol. 57, # 2, p. 95 - 99

  摘要：

  DOI：
• 作为产物：
  描述：

  racem. 2,2'-methanediyl-bis-cyclohexanone 在 Raney NI/Ru 甲酸 、 氨 、 氢气 作用下， 生成 (4aα,8aα,9aβ,10aα)-tetradecahydro-10-methylacridine
  参考文献：
  名称：

  饱和的含氮杂环。13.全氢ac啶。合成与立体化学

  摘要：

  DOI：

  10.1007/bf00472257

文献信息

• Formation of nitrogen heterocycles in the hydroamination of 1,5-diketones
  作者：V. G. Kharchenko、A. P. Kriven'ko、O. V. Fedotova、T. G. Nikolaeva

  DOI：10.1007/bf00568950

  日期：1982.7
• Hydroacridines XXI [1]. 13C NMR Spectroscopic Investigation of the Stereoselectivities of Quaternizations of N-Alkyl Derivatives of (4aα,8aβ,9aβ,10aα)- and (4aα,8aα,9aβ,10aα)-Tetradecahydroacridine
  作者：Francisc Potmischil、Helmut Herzog、Joachim Buddrus、Mircea D. Gheorghiu

  DOI：10.1007/pl00010310

  日期：2000.1
• Hydroacridines. Part 17—Stereospecific influence of the N+—O- group on1JC,C couplings in non-aromatic amine oxides
  作者：Francisc Potmischil、Helmut Herzog、Joachim Buddrus

  DOI：10.1002/(sici)1097-458x(199804)36:4<240::aid-omr260>3.0.co;2-9

  日期：1998.4

  The (1)J(C,C) coupling constants of N-epimeric pairs of amine oxides derived from (4a alpha, 8a beta, 9a beta, 10a alpha)- and (4a alpha, 8a alpha, 9a alpha, 10a alpha)-tetradecahydro-10-methylacridine, 1-cis-2,6-trimethylpiperidine and tropine were investigated and compared with those for the parent amines. For C-C bonds adjacent to the N+-O- group, the couplings depend on the mutual orientation of the N+-O- bond and the C-C bond of interest: with the N+-O- bond oriented sm (gauche), the couplings are essentially as large as those in the parent amines, whereas with the N+-O- bond oriented anti, the couplings are about 4-5 Hz smaller. The C-13 NMR chemical shifts of the N-CH3 carbons, from which the configurations of the N-epimeric amine oxides can be derived, are also reported. (C) 1998 John Wiley & Sons, Ltd.
• Hydroacridines XVIII [1]. Synthesis and NMR Spectroscopic Investigation of(4aα,8aβ,9aα,10aβ)-Tetradecahydroacridine and Some of its Derivatives
  作者：Francisc Potmischil、Friedrich W. Vierhapper、Hermann Kalchhauser

  DOI：10.1007/pl00000108

  日期：1998.5

  The reductive amination of (R*,R*)-2,2'-methylene-bis-cyclohexanone (1) with methylamine and potassium borohydride affords a mixture of (4a alpha,8a beta,9a alpha,10a beta)- and (4a alpha,8a alpha,9a beta,10a alpha)-tetradecahydro-10-methylacridine (2, 3) in a ratio of approximately 1.3:1 in 57% overall yield. By N-demethylation of 2, via the N-nitrosamine 4 the first synthesis of (4a alpha,8a beta,9a alpha,10a beta)-tetradecahydroacridine (5) could be performed. The relative configurations and conformations of compounds 2-5 as well as the barrier of conformational inversion of 5(Delta G(300)(#), = 55.5 +/- 0.4kJ.mol(-1)) were determined by NMR spectroscopy.
• KRIVENKO, A. P.;NIKOLAEVA, T. G.;YUDOVICH, L. M.;KOMYAGIN, N. T.;YANOVSKI+, XIMIYA GETEROTSIKL. SOED.,(1987) N 12, 1645-1650
  作者：KRIVENKO, A. P.、NIKOLAEVA, T. G.、YUDOVICH, L. M.、KOMYAGIN, N. T.、YANOVSKI+

  DOI：——

  日期：——