SYNTHESIS OF 4-SUBSTITUTED BICYCLO[2.2.2]OCT-1-YL FLUORIDES
SYNTHESIS OF 4-SUBSTITUTED BICYCLO[2.2.2]OCT-1-YL FLUORIDES
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DOI：
10.1021/jo00136a028
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发表时间：
1982-01-01
影响因子：
3.6
通讯作者：
ABEYWICKREMA, AN
中科院分区：
文献类型：
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作者：
ADCOCK, W;ABEYWICKREMA, AN
合成了一系列4-取代的（X）双环[2.2. 2]介绍了取代基效应研究所需的辛基氟化物（1）。这些化合物[1，X= NO2，CN，CONH 2，COCH 3，CHO，OCH 3，OCOCH 3，OH，F，Cl，Br，I，NH 2，N（CH 3）2，NHCOCH 8，C2 H5，i-C3 H7，和Sn（CH 8）3]中的大多数的合成已经由4-氟双环[2.2. 2]辛烷-1-羧酸（1，X= COOH）的反应。关键的新前体化合物（1，X= COOH）由4-甲氧基双环[2.2. 2]辛烷-1-羧酸（7），其又由4-乙酰基-4-（乙氧羰基）庚二酸（2）以良好的产率构建。1-叔丁基-4-氟双环[2.2. 2]辛烷（I，X= C（CHg）g）由7经由1-叔丁基-4-甲氧基二环[2.2. 2]辛烷值1-氟双环[2.2. 2]辛烷（1，X=
The main details of the synthesis of a series of 4-substituted (X) bicyclo [2.2. 2] oct-l-yl fluorides (1), which were required for substituent effect studies, are presented. The synthesis of most of these compounds [1, X= N02, CN, CONH2, COCH3, CHO, OCH3, OCOCH3, OH, F, Cl, Br, I, NH2, N (CH3) 2, NHCOCHg, C2H5, i-C3H7, and Sn (CHg) 3] has been accomplished from 4-fluorobicyclo [2.2. 2] octane-l-carboxylic acid (1, X= COOH) in a straightforward fashion using fairly standard functionalization procedures. The key new precursor compound (1, X= COOH) was prepared from 4-methoxybicyclo [2.2. 2] octane-l-carboxylic acid (7) which, in turn, was constructed from 4-acetyl-4-(ethoxycarbonyl) pimelic acid (2) in good yield. l-tert-Butyl-4-fluorobicyclo [2.2. 2] octane (1, X= C (CHg) g) was obtained from 7 via l-tert-butyl-4-methoxybicyclo [2.2. 2] octane. l-Fluorobicyclo [2.2. 2] octane (1, X=