Name: Mequinol. Authors Han, KH; Wang, YY; Zhao, P; You, XH; Wang, J; Guo, YC; Zhao, YF; Cao, SX in AMER CHEMICAL SOC published article about in [Han, Kehui; Wang, Yanyan; Zhao, Pei; You, Xiaohui; Wang, Jun; Guo, Yanchun; Zhao, Yufen; Cao, Shuxia] Zhengzhou Univ, Coll Chem, Green Catalysis Ctr, Zhengzhou 450001, Peoples R China; [Zhao, Yufen] Ningbo Univ, Inst Drug Discovery Technol, Ningbo 315211, Peoples R China in 2021, Cited 45. The Name is Mequinol. Through research, I have a further understanding and discovery of 150-76-5
The stereochemical mechanism of the nucleophilic substitution reaction at pentacoordinate phosphorus (P-V) atom is rarely studied. Here, we report the Atherton-Todd-type reaction of pentacoordinate hydrospirophosphorane with phenolic compounds in detail. The stereochemical mechanism of nucleophilic substitution at P-V atom was proposed by P-31 NMR tracing experiment, X-ray diffraction analysis, and density functional theory calculations. The first step of the Atherton-Todd-type reaction is the formation of halogenated spirophosphorane intermediate with retention of configuration at phosphorus definitely. The second step is a nucleophilic substitution reaction at P-V atom of halogenated spirophosphorane. When using CCl4 as a halogenating agent, the reaction of chlorinated spirophosphorane proceeds via S(N)2(P-V) mechanism, and the backside attack of P-Cl bond is the main pathway. For chlorinated spirophosphorane with Delta(P) configuration, the completely P-inverted product is normally obtained. As for chlorinated spirophosphorane with Lambda(P) configuration, which has larger steric hindrance behind P-Cl bond, the proportion of P-retained products apparently increases and a pair of diastereoisomers is acquired. Furthermore, if CBr4 is used as a halogenating agent, the nucleophilic substitution reaction of brominated spirophosphorane may go through a S(N)1(P-V) mechanism to afford a pair of diastereoisomers.
Name: Mequinol. About Mequinol, If you have any questions, you can contact Han, KH; Wang, YY; Zhao, P; You, XH; Wang, J; Guo, YC; Zhao, YF; Cao, SX or concate me.
Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
,Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles