一鍋化型式的巴比艾爾及氧化反應合成丙炔基酮與丙炔基醇

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Title:	一鍋化型式的巴比艾爾及氧化反應合成丙炔基酮與丙炔基醇
Other Titles:	One-pot synthesis of propargylic alcohol and ketone via barbier reaction and oxidation
Authors:	吳鐵綱;Wu, Tieh-Kang
Contributors:	淡江大學化學學系碩士班李世元;Lee, Shih-Yuan
Keywords:	一鍋化;巴比艾爾;氧化;丙炔基酮;丙炔基醇;Propargylic Ketone;Propargylic Alcohol;One-pot;Barbier Reaction;Acetylenic Ketone;oxidation
Date:	2014
Issue Date:	2015-05-01 16:11:11 (UTC+8)
Abstract:	丙炔基酮類化合物可以用做抗菌抗黴劑添加在化妝品與食品當中，以防止微生物繁殖造成的腐敗與變質。而過去的丙炔基酮化合物合成方法多透過氧化丙炔基醇製備，但此方法需要先合成丙炔基醇，所以需要兩步驟合成丙炔基酮。而另一種合成方式以醯基鹵化物為起始物可一步合成丙炔基酮，但醯基鹵化物多數不穩定且難予製備。為了改善過去合成丙炔基酮的不便之處，本論文提出以一鍋化的巴比艾爾反應與氧化反應合成丙炔基酮，不但步驟簡化，且起始物為穩定的醛類化合物。本論文用醛類化合物為起始物，將其加入在超音波促進巴比艾爾反應中以鎂金屬及溴苯形成格林納試劑去質子化的苯乙炔反應，再加入氧化劑PCC後便可得到丙炔基酮化合物。 Propargylic Ketone derivatives were employed as antiseptic in cosmeticians and foods. Many synthetic methods for preparation of propargylic ketone have been reported. Among these reported methods, the common used method was deprotonation of terminal alkyne and then reacted with aldehyde, further oxidation of propargylic alcohol to afford propargylic alcohol. A direct method was terminal alkyne which was reacted with acyl halide by introducing transition metal as catalyst. This paper presented a new method of one-pot systhesis of propargylic ketone from Aldehyde. We can obtain propargylic ketone in one-pot reaction by reaction of the aldehyde with deprotonated phenylacetylene via Barbier reaction and then a PCC was added to the reaction mixture.
Appears in Collections:	[Graduate Institute & Department of Chemistry] Thesis

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