Chemistry of trans-Resveratrol with Singlet Oxygen: [2+2] Addition, [4+2] Addition, and Formation of the Phytoalexin Moracin M
Chemistry of trans-Resveratrol with Singlet Oxygen: [2+2] Addition, [4+2] Addition, and Formation of the Phytoalexin Moracin M
复制标题
DOI：
10.1021/ol201922u
复制
发表时间：
2011-09-16
期刊：
影响因子：
5.2
通讯作者：
Selke, Matthias
中科院分区：
文献类型：
--
作者：
Celaje, Jeff A.;Zhang, Dong;Selke, Matthias
白藜芦醇（1）通过两种主要途径与单线态氧反应：[2 + 2]环加成形成瞬时二氧杂环丁烷，裂解成相应的醛;[4 + 2]环加成形成内过氧化物，加热后重排为莫拉克因M。通过时间分辨红外发光光谱法测定，在CD 3 OD中单线态氧被1（k（T））去除的速率常数为1.5 x 10（6）M-1 sec（-1），小于先前报道的值。化学反应占。k（T）的25%。
Resveratrol (1) reacts with singlet oxygen by two major pathways: A [2 + 2] cycloaddition forming a transient dioxetane that cleaves into the corresponding aldehydes and a [4 + 2] cycloaddition forming an endoperoxide that, upon heating, undergoes a rearrangement to moracin M. The rate constant by which singlet oxygen is removed by 1(k(T)) was determined by time-resolved infrared luminescence spectroscopy to be 1.5 x 10(6) M-1 sec(-1) in CD3OD, smaller than previously reported values. Chemical reaction accounts for ca. 25% of k(T).