(trans)-3,9,9-trimethyloctahydroacridine

• 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)-3,9,9-trimethyloctahydroacridine
• 英文别名: (3R,4aS,9aR)-3,9,9-trimethyl-2,3,4,4a,9a,10-hexahydro-1H-acridine
• 化学式: C₁₆H₂₃N
• 分子量: 229.365
• InChiKey: PIGHVUCWIPFICY-ZLDLUXBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 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 、 苯胺 以 甘油 为溶剂， 反应 7.0h， 生成 (3R,4aS,9aS)-3,9,9-Trimethyl-1,2,3,4,4a,9,9a,10-octahydroacridine 、 (trans)-3,9,9-trimethyloctahydroacridine
  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

• Selenium- and tellurium-based ionic liquids and their use in the synthesis of octahydroacridines
  作者：Eder J. Lenardão、Samuel R. Mendes、Patrícia C. Ferreira、Gelson Perin、Claudio C. Silveira、Raquel G. Jacob

  DOI：10.1016/j.tetlet.2006.08.049

  日期：2006.10

  A general and easy method for the synthesis of several selenonium and telluronium salts is described. These compounds are acidic liquids at room temperature and were obtained in excellent yields. Phenyl butyl ethyl selenonium tetrafluoroborate was employed in the hetero-Diels-Alder cyclization of aryl imines derived from citronellal, affording octahydroacridines in good yields. (c) 2006 Elsevier Ltd. All rights reserved.
• 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.