本篇主要是研究含薁核α-羥基酯類及其前驅物含薁核α-酮基酯類之合成,因α-羥基酯類衍生物具有抗精神病效果(antipsychotics),及含薁核衍生物具有降低膽固醇、抗潰瘍、抗發炎、抗高血質的效果。應用Friedel-Crafts醯化(acylation)的方法合成3-(乙氧羰基甲醯基)薁-1-羧酸酯類衍生物,係將自行製備之薁-1-羧酸酯類的衍生物原料,溶於氯苯中,然後加入三氯化鋁催化劑,再加入草酸氯乙酯,在120℃下反應4小時,而得3-(乙氧羰基甲醯基)薁-1-羧酸乙酯、2-乙氧基-3-(乙氧羰基甲醯基)薁-1-羧酸乙酯、2-羥基-3-(乙氧羰基甲醯基)薁-1-羧酸乙酯、3-(乙氧羰基甲醯基)薁-1-羧酸甲酯、2,4-二乙氧基-1-(乙氧羰基甲醯基)薁及2,4-二乙氧基-1,3-二(乙氧羰基甲醯基)薁等含薁核α-酮基酯類前驅物;其中前驅物2-乙氧基-3-(乙氧羰基甲醯基)薁-1-羧酸乙酯和3-(乙氧羰基甲醯基)薁-1-羧酸甲酯分別與格林納(Grignard)試劑(異丙基鎂氯)於0℃下反應40分鐘,可得到3-(1-乙氧羰基-2-甲基-1-羥基丙基)薁-1-羧酸甲酯和2-乙氧基-3-(1-乙氧羰基-2-甲基-1-羥基丙基)薁-1-羧酸乙酯等含薁核α-羥基酯類。以上化合物及前驅物結構的決定依紅外線光譜(IR)、核磁共振光譜(NMR)及質譜(Mass)鑑定之。
The aim of this study is to synthesize α-xyl hydroesters azulene and it's precursor α-keto esters azulene. The α-hydroxyl ester derivatives have long been known for their antipsychotics effect,and azulene derivatives have long been known for their hypocholesterolemic effect and anti-ulcerative, anti-inflammatory and antihyperlipidemic activity. The reaction we apply to synthesize ethyl 3-(ethoxycarbonylformyl)azulene -1-carboxylate derivatives is Friedel-Crafts Acylation. These derivatives were prepared by reaction of azulene-1-carboxylate derivatives with aluminium chloride (AlCl3) and ethyl chloro glyoxylate in chlorobenzene at 120℃ for 4hrs. The precusors reported in this thesis include ethyl 3-(ethoxycarbonylformyl) azulene-1- carboxylate, ethyl 2-ethoxy-3-(ethoxycarbonylformyl) azulene-1-carboxylate, 2-hydroxy-3-(ethoxycarbonylformyl) azulene-1-carboxylate, methyl 3-(ethoxycarbonylformyl)azulene -1-carboxylate, 2,4-diethoxy-3-(ethoxycarbonylformyl)azulene and 2,4-diethoxy-1,3-di(ethoxycarbonylformyl)azulene. Reactions of the precursors ethyl 2-ethoxy-3- (ethoxycarbonylformyl)azulene-1-carboxylate and methyl 3-(ethoxycarbonylformyl)azulene-1-carboxylate reacted with isopropylmagnesium chloride at 0℃ for 40 min. afforded methyl 3-(1-ethoxycarbonyl-2- methyl -1- hydroxylpropyl) azulene-1-carboxylate and ethyl 2-ethoxy-3- (1-ethoxycarbonyl- 2-methyl -1- hydroxylpropyl)azulene-1-carboxylate, respectively. These new compounds were characterized by IR, NMR and Mass spectra.
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