982. Higher aliphatic compounds. Part X. A synthesis of tariric and petroselinic acids
982. Higher aliphatic compounds. Part X. A synthesis of tariric and petroselinic acids
复制标题
982.高级脂肪族化合物。
DOI：
10.1039/jr9520005032
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发表时间：
1952
期刊：
影响因子：
--
通讯作者：
J. C. Smith
中科院分区：
文献类型：
--
作者：
P. Lumb;J. C. Smith
三里酸，其甘油三酯形成高达90%的脂肪从毕节属猪(Steger和Van Loon，Rec.特雷弗。Chim.，1933，52,593)，由Arnaud(Comfit.1892,114，79；1896,122,100；1902,134,473)是一种乙炔化合物，八碳-6-乙烯酸。该酸由十三炔基锂与L-氯-3-碘丙烷反应生成L-氯十六烷-4-炔，再转化为L-碘十六烷-4-炔，再经丙二酸酯合成得到固体十六烷基丙二酸。在脱羧基作用下形成的八碳-6-ynoic酸j-在性质上与天然三甲酸的性质一致，并得到与记录的天然三聚酸相同的衍生物。钠盐用氢和雷尼镍部分还原得到顺式八碳-6-烯酸，与石油硒酸相同，其甘油酯形成高达欧芹种子油(和其他香菜属植物的油)75%的脂肪。有趣的是，在艾哈迈德之后，Bumpus和Strong(J.Amer)。化学。Soc.，1948，70,3391)，Taylor和Strong(同上，1950，72,4263)由L-氯-9-碘烷和辛基钠合成(反式-八碳-1，L-烯酸)酸(随后经氰化物合成和部分还原)，未能得到石油酸(同上，1950，72,4363)。1948，42,581)应被视为本系列的第九部分；第八部分，J.T日内瓦命名法(C0，H=1)。
TARIRIC ACID, the glyceride of which forms up to 90% of the fat of seeds from Picrainnia Sow (Steger and Van Loon, Rec. Trav. chim., 1933, 52, 593), was shown by Arnaud (Comfit. rend., 1892, 114, 79; 1896, 122,100; 1902, 134,473) to be an acetylenic compound, octadec-6-ynoic acid. This acid has now been synthesised by using the reaction between tridecynyllithium and l-chloro-3-iodopropane to yield l-chlorohexadec-4-yne which, after conversion into l-iodohexadec-4-yne gives, by the malonic ester synthesis, solid hexadec-4-ynylmalonic acid. The octadec-6-ynoic acid j-which is formed on decarboxylation agrees in properties with, and gives derivatives identical with those recorded for, natural tariric acid. Partial reduction of the sodium salt with hydrogen and Raney nickel gave cis-octadec-6-enoic acid, identical with petroselinic acid, the glyceride of which forms up to 75% of the fat of parsley seed oil (and the oils of other UmbeZZiferae). It is interesting that after Ahmad, Bumpus, and Strong (J. Amer. Chem. Soc., 1948, 70, 3391) had synthesised vaccenic (trans-octadec-1 l-enoic) acid from l-chloro-9-iodononane and octynylsodium (followed by the cyanide synthesis and partial reduction of the octadec-1 l-ynoic acid), Taylor and Strong (ibid., 1950, 72, 4263) failed to obtain petroselinic acid by* A Synthesis of Hydnocarpic Acid (Diaper and Smith, Biochem. J., 1948, 42, 581) is to be regarded as Part IX of this series; Part VIII, J., 1939, 974. t Geneva nomenclature (C0, H= 1).