(trans)-3,7,9,9-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)-3,7,9,9-tetramethyloctahydroacridine
• 英文别名: (3R,4aS,9aR)-3,7,9,9-tetramethyl-2,3,4,4a,9a,10-hexahydro-1H-acridine
• 化学式: C₁₇H₂₅N
• 分子量: 243.392
• InChiKey: DHCGNBWUSPLFOV-WWGRRREGSA-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 、 乙烷,三氯氟- 以 甘油 为溶剂， 反应 16.0h， 生成 cis-3,7,9,9-tetramethyloctahydroacridine 、 (trans)-3,7,9,9-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

• 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.
• 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.
• Catalyst-free synthesis of octahydroacridines using glycerol as recyclable solvent
  作者：José E.R. Nascimento、Angelita M. Barcellos、Maraísa Sachini、Gelson Perin、Eder J. Lenardão、Diego Alves、Raquel G. Jacob、Fabiana Missau

  DOI：10.1016/j.tetlet.2011.03.045

  日期：2011.5

  herein the use of glycerol as an efficient, safe and recyclable solvent in the one-pot hetero-Diels–Alder (HDA) reaction of (R)-citronellal with substituted arylamines. The catalyst-free reactions proceed easily using glycerol at 90 °C and the corresponding octahydroacridines (OHAs) were obtained in good to excellent yields by simply decantation of products. After removing the products, glycerol was directly

  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。