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喹啉生物碱哈普菲林定溴化过程中的分子内环化反应。

Intramolecular Cyclization During Bromination of the Quinoline Alkaloid Haplophyllidine.

作者信息

Ubaidullaev A U, Vinogradova V I, Zhurakulov Sh N, Mukarramov N I, Bobakulov Kh M, Turgunov K A, Tashkhodzhaev B

机构信息

S. Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, Uzbekistan.

M. Ulugbek National University of Uzbekistan, Tashkent, Uzbekistan.

出版信息

Chem Nat Compd. 2022;58(6):1101-1107. doi: 10.1007/s10600-022-03877-6. Epub 2022 Nov 15.

Abstract

Bromination of the furanoquinoline alkaloid haplophyllidine by molecular bromine and -bromosuccinimide was accompanied by intramolecular cyclization to form mixtures of new compounds containing additional penta-, hexa-, and spirocyclic rings incorporating the prenyl group of haplophyllidine. The structures and absolute configurations of the chiral centers of all four bromo-derivatives were elucidated using a combination of NMR spectroscopic methods and X-ray crystal structure analyses.

摘要

呋喃喹啉生物碱哈普菲林(haplophyllidine)与分子溴和N-溴代琥珀酰亚胺发生溴化反应时,伴随着分子内环化,形成了新化合物的混合物,这些新化合物含有额外的五环、六环和螺环,并入了哈普菲林的异戊烯基。使用核磁共振光谱方法和X射线晶体结构分析相结合的方式,阐明了所有四种溴代衍生物手性中心的结构和绝对构型。

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