文献类型：期刊文献

中文题名：萘并呋喃类化合物的染料化光氧化及其杂环衍生物的合成与表征

英文题名：Syntheses and Characterizations of the Dye Sensitized Photooxygenation Products and the Heterocycles of Naphthofuran Derivatives

作者：钱旭红[1];张玉兰[1]

机构：[1]华东理工大学,药物化工所,上海200237

年份：1997

卷号：17

期号：4

起止页码：329

中文期刊名：有机化学

外文期刊名：Chinese Journal of Organic Chemistry

收录：CSTPCD;;Scopus;北大核心:【北大核心1996】；CSCD:【CSCD2011_2012】；

基金：国家教育委员会;国家自然科学基金会;德国洪堡基金会(AvH)

语种：中文

中文关键词：萘并呋喃;光氧化;染料敏化;环构;呋喃并香豆素

外文关键词：naphthof urans, dye sensitization, photochemistry, cyclization, characterization

摘要：萘并呋喃类化合物1、7在四苯基卟啉存在与氧低温反应给出相应的二氧杂环丁烷类产物2、8,室温下分别全部分解成乙酰基乙酰氧基化合物4、9。2和盐酸作用可给出呋喃3-位甲基及所在萘半环β位的二氯代产物6。4与盐酸反应通过失去萘α位的酰基,形成羟基呋喃化合物3,1在三溴化硼酸解下亦可得同一产物。4在醋酸钠/醋酐中环构生成3-乙酰基吡喃酮(5)。
In the presence of tetraphenylporphine and oxygen under irradiation of light at low temperature , naphthofurans 1 and 7 formed the corresponding dioxetanes 2 and 8 , and followed by decomposition at room temperature to acetylacetoxyl naphthalene 4 and 9 , respectively . 2 reacted with hydrogenchloride to give naphthofuran 6 , in which two hydrogens at 3 - methyl group and 9 - position near the furan ring were substituted by chlorine group . 4 reacted with hydrogen chloride form hydroxy naphthofuran 3 by losing an acetyl group at its a - position , the same product was obtained by the ac tion of 1 with BBr3 . In the presence of sodium acetate / acetic anhydride 4 cyclized to give 3 - acetyl naphthopyrone 5 . The structures of the above compounds were confirmed by using 1 H , 13 C -NMR,IR,MS,UV,FL and elemental analysis,their synthetic mechanism were also suggested.