N-nitroso-trans-syn-trans-perhydroacridine | 24506-23-8

• 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: N-nitroso-trans-syn-trans-perhydroacridine
• 英文别名: (4aR,8aR,9aS,10aS)-10-nitroso-2,3,4,4a,5,6,7,8,8a,9,9a,10a-dodecahydro-1H-acridine
• CAS: 24506-23-8
• 化学式: C₁₃H₂₂N₂O
• 分子量: 222.33
• InChiKey: QXXRCLOCRJUTQN-FNFFVJSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 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：
  32.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-nitroso-trans-syn-trans-perhydroacridine 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 生成 (4aβ,8aβ,9aβ,10aα)-tetradecahydro-10-nitrosoacridine
  参考文献：
  名称：

  Hydroacridines XXV [1]. First Synthesis of (4aα,8aα,9aβ,10aβ)-Tetradecahydroacridine and New Syntheses of (4aα,8aα,9aα,10aβ)- and (4aα,8aβ,9aα,10aβ)-Tetradecahydroacridine

  摘要：

  On heating in dry DMSO, in the presence of potassium t-butoxide, the N-nitrosamine of (4a alpha,8a beta,9a beta,10a alpha)-tetradecahydroacridine is completely converted into the N-nitrosamine of (4a alpha,8a alpha,9a alpha,10a beta)-tetradecahydroacridine. Under similar conditions, the N-nitrosamine of (4a alpha,8a alpha,9a beta,10a alpha)-tetradecahydroacridine yields a ternary equilibrium mixture containing itself (19%), and the N-nitrosamines of (4a alpha,8a beta,9a alpha,10a beta)-tetradecahydroacridine (46%) and the so far unknown (4a alpha,8a alpha,9a beta,10a beta)-tetradecahydroacridine (35%). The resulting N-nitrosamines can be smoothly denitrosated to the corresponding secondary amines.

  DOI：

  10.1007/s00706-006-0551-8
• 作为产物：
  描述：

  trans,syn,trans-perhydroacridine 在 亚硝酸乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 N-nitroso-trans-syn-trans-perhydroacridine
  参考文献：
  名称：

  N-Nitrosodecahydroquinolines. Conformational analysis by carbon-13 nuclear magnetic resonance spectroscopy

  摘要：

  DOI：

  10.1021/jo01303a036

文献信息

• VIERHAPPER F. W., J. ORG. CHEM., 1980, 45, NO 15, 3111-3118
  作者：VIERHAPPER F. W.

  DOI：——

  日期：——
• N-Nitrosodecahydroquinolines. Conformational analysis by carbon-13 nuclear magnetic resonance spectroscopy
  作者：Friedrich W. Vierhapper

  DOI：10.1021/jo01303a036

  日期：1980.7
• Hydroacridines XXV [1]. First Synthesis of (4aα,8aα,9aβ,10aβ)-Tetradecahydroacridine and New Syntheses of (4aα,8aα,9aα,10aβ)- and (4aα,8aβ,9aα,10aβ)-Tetradecahydroacridine
  作者：Francisc Potmischil、Joachim Buddrus、Jörg Lambert

  DOI：10.1007/s00706-006-0551-8

  日期：2006.12

  On heating in dry DMSO, in the presence of potassium t-butoxide, the N-nitrosamine of (4a alpha,8a beta,9a beta,10a alpha)-tetradecahydroacridine is completely converted into the N-nitrosamine of (4a alpha,8a alpha,9a alpha,10a beta)-tetradecahydroacridine. Under similar conditions, the N-nitrosamine of (4a alpha,8a alpha,9a beta,10a alpha)-tetradecahydroacridine yields a ternary equilibrium mixture containing itself (19%), and the N-nitrosamines of (4a alpha,8a beta,9a alpha,10a beta)-tetradecahydroacridine (46%) and the so far unknown (4a alpha,8a alpha,9a beta,10a beta)-tetradecahydroacridine (35%). The resulting N-nitrosamines can be smoothly denitrosated to the corresponding secondary amines.