(3R,4aR,9aS)-3,9,9-Trimethyl-1,2,3,4,4a,9,9a,10-octahydroacridine

• 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: (3R,4aR,9aS)-3,9,9-Trimethyl-1,2,3,4,4a,9,9a,10-octahydroacridine
• 英文别名: trans-3,9,9-trimethyloctahydroacridine；(3R,4aR,9aS)-3,9,9-trimethyl-2,3,4,4a,9a,10-hexahydro-1H-acridine
• 化学式: C₁₆H₂₃N
• 分子量: 229.365
• InChiKey: PIGHVUCWIPFICY-UXIGCNINSA-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 在 bismuth(III) chloride 作用下， 以 乙腈 为溶剂， 以98%的产率得到(3R,4aR,9aS)-3,9,9-Trimethyl-1,2,3,4,4a,9,9a,10-octahydroacridine
  参考文献：
  名称：

  Bismuth(III) Chloride: An Efficient Catalyst for the One-Pot Stereoselective Synthesis of Octahydroacridines

  摘要：

  报告了一种立体可控制备八氢吖啶衍生物的单锅程序，该程序涉及由香茅醛和芳香胺原位生成的 N-芳基亚胺的分子内异狄尔斯-阿尔德反应。反应介质的温度对确定反式/顺式比率起着关键作用。

  DOI：

  10.1055/s-2002-20045

文献信息

• Ionic liquid accelerated intramolecular hetero-Diels–Alder reactions: a protocol for the synthesis of octahydroacridines
  作者：J.S. Yadav、B.V.S. Reddy、Lakshindra Chetia、G. Srinivasulu、A.C. Kunwar

  DOI：10.1016/j.tetlet.2004.11.137

  日期：2005.2

  2-Azadienes derived in situ from arylamines and (R)-(+)-citronellal/3-methylcitronellal undergo intramolecular [4+2] hetero-Diels–Alder reactions in the air and moisture stable ionic liquid [bmim]BF4 in the absence of any acid catalyst to afford 1,2,3,4,4a,9,9a,10-octahydroacridine derivatives in high to quantitative yields.

  原位衍生自芳基胺和（R）-（+）-香茅醛/ 3-甲基香茅醛的2-氮杂二烯在空气中和湿气稳定的离子液体[bmim] BF 4中发生分子内[4 + 2]杂Diels-Alder反应。不存在任何酸催化剂，以高到定量的产率得到1,2,3,4,4a，9,9a，10-八氢ac啶衍生物。
• 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.
• Bismuth(III) Chloride: An Efficient Catalyst for the One-Pot Stereoselective Synthesis of Octahydroacridines
  作者：Gowravaram Sabitha、Erigala Venkata Reddy、Jhillu S. Yadav

  DOI：10.1055/s-2002-20045

  日期：——

  A one-pot procedure for the stereocontrolled preparation of octahydroacridine derivatives is reported, which involves the intramolecular hetero-Diels-Alder reaction of N-arylimines produced in situ from citronellal and aromatic amines. The temperature of the reaction medium plays a key role in determination of the trans/cis ratio.

  报告了一种立体可控制备八氢吖啶衍生物的单锅程序，该程序涉及由香茅醛和芳香胺原位生成的 N-芳基亚胺的分子内异狄尔斯-阿尔德反应。反应介质的温度对确定反式/顺式比率起着关键作用。