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N-{4-溴-2-[(S)-薄荷氧基]-5-氧代-2,5-二氢-3-呋喃基}-L-缬氨酸

N-{4-Bromo-2-[(S)-menth-yloxy]-5-oxo-2,5-dihydro-3-fur-yl}-l-valine.

作者信息

Song Xiu-Mei, Li Zhao-Yang, Wang Zhao-Yang, Fu Jian-Hua

机构信息

School of Chemistry and the Environment, South China Normal University, Guangzhou 510006, People's Republic of China.

出版信息

Acta Crystallogr Sect E Struct Rep Online. 2009 Jul 11;65(Pt 8):o1838. doi: 10.1107/S1600536809026129.

DOI:10.1107/S1600536809026129
PMID:21583539
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2977280/
Abstract

The title compound, C(19)H(30)BrNO(5), was obtained via a tandem asymmetric Michael addition-elimination reaction of 3,4-dibromo-5-[(S)-l-menth-yloxy]furan-2(5H)-one and l-valine in the presence of potassium hydroxide. The mol-ecular structure contains an approximately planar (r.m.s. deviation = 0.0204 Å) five-membered furan-one ring and a six-membered menth-yloxy ring adopting a chair conformation. The crystal packing is stabilized by inter-molecular O-H⋯O and N-H⋯O hydrogen bonding.

摘要

标题化合物C(19)H(30)BrNO(5)是通过3,4-二溴-5-[(S)-薄荷氧基]呋喃-2(5H)-酮与L-缬氨酸在氢氧化钾存在下进行串联不对称迈克尔加成-消除反应得到的。分子结构包含一个近似平面的（均方根偏差 = 0.0204 Å）五元呋喃-酮环和一个呈椅式构象的六元薄荷氧基环。晶体堆积通过分子间的O-H⋯O和N-H⋯O氢键得以稳定。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3fea/2977280/acb78559b3d6/e-65-o1838-fig1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3fea/2977280/acb78559b3d6/e-65-o1838-fig1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3fea/2977280/acb78559b3d6/e-65-o1838-fig1.jpg

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本文引用的文献

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N-[(2S)-4-Chloro-2-(l-menthyloxy)-5-oxo-2,5-dihydro-3-furyl]-l-alanine.N-[(2S)-4-氯-2-(L-薄荷氧基)-5-氧代-2,5-二氢-3-呋喃基]-L-丙氨酸
Acta Crystallogr Sect E Struct Rep Online. 2009 Apr 10;65(Pt 5):o1030. doi: 10.1107/S1600536809012720.
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Synthesis of combinatorial libraries of 3,4,5-trisubstituted 2(5H)-furanones. Part Two: Construction of a library of 4-amino-5-alkoxy-2(5H)-furanones.3,4,5-三取代-2(5H)-呋喃酮组合库的合成。第二部分：4-氨基-5-烷氧基-2(5H)-呋喃酮库的构建。
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