桦木醛的自氧化产物。

Autoxidation Products of Betulonaldehyde.

作者信息

Ayers Sloan, Benkovics Tamas, Marshall Jonathan, Tan Yichen, Strotman Neil A, Kiau Susanne

机构信息

Bristol-Myers Squibb Co. , Chemical & Synthetic Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States.

出版信息

J Nat Prod. 2016 Oct 28;79(10):2758-2761. doi: 10.1021/acs.jnatprod.6b00735. Epub 2016 Sep 29.

DOI:10.1021/acs.jnatprod.6b00735

PMID:27684353

Abstract

Three major degradation products resulted from the exposure of betulonaldehyde (1) to air in solution at room temperature. From HRMS and NMR data, the products, which were isolated by preparative supercritical fluid chromatography (SFC), were identified as betulonic acid (2) and C-17 hydroperoxide epimers 3 (β-OOH) and 4 (α-OOH). For 3 and 4, the H-18 multiplet pattern of the isolated products established the configuration at C-17.

摘要

在室温下，桦木醛（1）在溶液中暴露于空气中产生了三种主要降解产物。通过高分辨质谱（HRMS）和核磁共振（NMR）数据，经制备型超临界流体色谱（SFC）分离得到的产物被鉴定为桦木酸（2）以及C-17氢过氧化物差向异构体3（β-OOH）和4（α-OOH）。对于3和4，分离产物的H-18多重峰模式确定了C-17处的构型。