Synthesis of 1,2,3,4,5,6,7,8-octahydroacridine via condensation of cyclohexanone with formaldehyde.
Synthesis of 1,2,3,4,5,6,7,8-octahydroacridine via condensation of cyclohexanone with formaldehyde.
复制标题
环己酮与甲醛缩合合成1,2,3,4,5,6,7,8-八氢吖啶。
DOI：
10.1021/jo005746u
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发表时间：
2001
期刊：
影响因子：
--
通讯作者：
Bell,TW
中科院分区：
文献类型：
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作者：
Pilato,ML;Catalano,VJ;Bell,TW
以1，2，3，4，5，6，7，8-八氢吖啶（1）1和9-取代的1，2，3，4，5，6，7，8-八氢吖啶为原料，合成了几种氢键受体和多齿配体。2因为1是有限商业可用性的有价值的起始材料，我们进行了其大规模合成。在制备1，3的许多方法中，基于9-丁基-1，2，3，4，5，6，7，8-八氢吖啶（2）的成功大规模合成，选择方案1中概述的两步法。4目前，用于合成1的最有效的方法需要三个步骤（总共51-71%）3b、d、k，并且涉及低熔点中间体2，2′-亚甲基双环己酮（5）（方案2）。该化合物及其高熔点异构体2-羟基三环-[7.3. 1.02，7]十三烷-13-酮（3）也是几个合成5和立体化学6研究的主题。本文报道了3合成的优化，它转化为1，以及沿着遇到的一种新的六环化合物的结构。
Several hydrogen-bonding receptors and polydentate ligands have been synthesized from 1, 2, 3, 4, 5, 6, 7, 8-octahydroacridine (1) 1 and from 9-substituted 1, 2, 3, 4, 5, 6, 7, 8-octahydroacridines. 2 Because 1 is a valuable starting material of limited commercial availability, we have undertaken its large scale synthesis. Of the many methods for the preparation of 1, 3 the two-step process outlined in Scheme 1 was chosen on the basis of the successful large scale synthesis of 9-butyl-1, 2, 3, 4, 5, 6, 7, 8-octahydroacridine (2). 4 Currently, the most efficient methods for the synthesis of 1 require three steps (51-71% overall) 3b, d, k and involve the low melting intermediate, 2, 2′-methylenebiscyclohexanone (5)(Scheme 2). This compound and its high-melting isomer, 2-hydroxytricyclo-[7.3. 1.02, 7] tridecan-13-one (3), have also been the subject of several synthetic5 and stereochemical6 studies. Reported herein are the optimization of the synthesis of 3, its conversion to 1, and the structure of a new hexacyclic compound encountered along the way.