(trans)-3,5,9,9-tetramethyloctahydroacridine

• 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: (trans)-3,5,9,9-tetramethyloctahydroacridine
• 英文别名: (3R,4aS,9aR)-3,5,9,9-tetramethyl-2,3,4,4a,9a,10-hexahydro-1H-acridine
• 化学式: C₁₇H₂₅N
• 分子量: 243.392
• InChiKey: JAMGCDSHKHVFRP-ZLDLUXBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (+)-香茅醛 、 邻甲苯胺 以 甘油 为溶剂， 反应 18.0h， 生成 (3R,4aS,9aS)-3,5,9,9-Tetramethyl-1,2,3,4,4a,9,9a,10-octahydroacridine 、 (trans)-3,5,9,9-tetramethyloctahydroacridine
  参考文献：
  名称：

  以甘油为可循环溶剂的无催化剂合成八氢ac啶

  摘要：

  我们在本文中描述了在（R）香茅醛与取代的芳基胺的一锅杂Diels-Alder（HDA）反应中，甘油作为一种有效，安全和可循环使用的溶剂的用途。使用甘油在90°C下轻松进行无催化剂反应，并通过简单地倾析产物，以良好或优异的收率获得相应的八氢ac啶（OHA）。除去产物后，将甘油直接重复用于进一步的HDA反应，而不会失去活性。

  DOI：

  10.1016/j.tetlet.2011.03.045

文献信息

• Intramolecular hetero-Diels-Alder reaction of N-arylimines. Applications to the synthesis of octahydroacridine derivatives
  作者：Sabine Laschat、Juergen Lauterwein

  DOI：10.1021/jo00062a033

  日期：1993.5

  A new intramolecular Lewis acid catalyzed hetero-Diels-Alder reaction of N-arylimines 5 with nonactivated olefins tethered to the 2-azadiene system was developed in order to prepare 1,2,3,4,-4a,9,9a,10-octahydroacridine derivatives 6. Both reactivity and cis/trans selectivity of 6 were mainly dependent on the substitution pattern in the 3-position of the cyclization precursor 5. The type of Lewis acid plays only a minor role in determination of the cis/trans ratio. The synthetic utility of this new cyclization was increased by performing it as a one-pot reaction (3+4-->6). Both absolute configuration and preferred conformation were assigned by detailed NMR studies.
• Clean and atom-economic synthesis of octahydroacridines: application to essential oil of citronella
  作者：Raquel G Jacob、Gelson Perin、Giancarlo V Botteselle、Eder J Lenardão

  DOI：10.1016/s0040-4039(03)01749-0

  日期：2003.9

  A green and efficient method for the synthesis of octahydroacridine (OHA) has been developed by a simple one-pot hetero-Diels-Alder reaction starting from (+)-citronellal and N-arylamines in the presence of a solid supported catalyst (SiO2/ZnCl2), under MW irradiation and without any solvent. The method was used in the direct preparation of OHA from citronella oil in good yield. (C) 2003 Elsevier Ltd. All rights reserved.