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首页> 外文期刊>Journal of the American Oil Chemists' Society >Reduction of fatty ester Δ2-isoxazoline heterocycles. Preparation of fatty esters containing the β-hydroxy ketone moietyheterocycles. Preparation of fatty esters containing the β-hydroxy ketone moiety
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Reduction of fatty ester Δ2-isoxazoline heterocycles. Preparation of fatty esters containing the β-hydroxy ketone moietyheterocycles. Preparation of fatty esters containing the β-hydroxy ketone moiety

机译：脂肪酸酯Δ2-异恶唑啉杂环的还原。含有β-羟基酮部分杂环的脂肪酸酯的制备。含有β-羟基酮部分的脂肪酯的制备

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摘要

Fatty ester compounds containing the β-hydroxy ketone moiety were prepared in good yields from their corresponding fatty Δ2-isoxazoline heterocyclic precursors by a reductive hydrogenolysis-hydrolysis procedure using Raney nickel as catalyst. By this methodology, C-17, C-18, and C-19 straight-chain fatty methyl esters containing the 10-hydroxy 12-keto moieties were prepared in 73, 83, and 92%, respectively, from their corresponding isoxazoline fatty ester compounds. Two other 10-hydroxy 12-keto C-12 and C-14 fatty ester compounds were prepared in 84 and 92% yield, respectively. The C-12 β-hydroxy ketone contains a phenyl ring at C-12, whereas the C-14 β-hydroxy ketone compound has two methyl substituents at C-13. GC-MS using electron impact ionization was used to determine the hydroxyl and ketone positions after conversion of the hydroxyl group into its corresponding trimethylsilyl ether. The precursor fatty ester Δ2-isoxazolines used in this study are readily available in one step from a 1,3-dipolar cycloaddition reaction between nitrile oxides and methyl 10-undecenoate. This overall two-step sequence, 1,3-dipolar cycloaddition followed by reductive ring opening, represent a convenient method to construct fatty ester compounds in good yields containing the β-hydroxy ketone functionality, an outcome not easily accessible by other methods.
机译：通过使用阮内镍作为催化剂，通过还原性氢解-水解方法，由它们相应的脂肪族Δ2-异恶唑啉杂环前体以高收率制备含有β-羟基酮部分的脂肪酯化合物。通过这种方法，分别从73、83和92％的相应的异恶唑啉脂肪酸酯中制备了含有10-羟基12-酮基的C-17，C-18和C-19直链脂肪甲基酯化合物。分别以84％和92％的收率制备了另外两种10-羟基12-酮C-12和C-14脂肪酸酯化合物。 C-12β-羟基酮在C-12处含有苯环，而C-14β-羟基酮化合物在C-13处具有两个甲基取代基。在将羟基转化成其相应的三甲基甲硅烷基醚之后，使用电子碰撞电离的GC-MS用于确定羟基和酮的位置。这项研究中使用的前体脂肪酯Δ2-异恶唑啉可以很容易地从腈氧化物和10-十一碳烯酸甲酯之间的1,3-偶极环加成反应中一步获得。这种整体的两步过程，即1,3-偶极环加成然后还原性开环，代表了一种方便的方法来以高收率构建含有β-羟基酮官能团的脂肪酯化合物，这种结果是其他方法不易获得的。

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