14-Acetylandrographolide

Autor: Rao Jada, Srinivasa, McMillan, Katherine, Hamzah, Ahmad, Saad, Mohammad, Lajis, Nordin, Stevens, Malcolm, Schwalbe, Carl, Stanslas, Johnson
Zdroj: Journal of Chemical Crystallography; February 2006, Vol. 36 Issue: 2 p93-97, 5p
Abstrakt: The title compound, 3-{2-[decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-napthalenyl]ethylidene}dihydro-4-acetoxy-2(3H)-furanone, C22H32O6, was synthesised from andrographolide. It crystallizes in the orthorhombic system with a= 7.4219(12), b= 11.8411(10), c= 23.777(4) Å in space group P212121. While the stereochemical relation between rings is slightly changed from the starting material, acetylation of the hydroxyfuranone moiety completely abolishes O--H$$ \cdots $$O hydrogen bonding there, leaving a C--H$$ \cdots $$O interaction. The hydrogen-bonded chains at the opposite end of the andrographolide molecule persist but reverse direction.The title compound, 3-{2-[decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-napthalenyl]ethylidene}dihydro-4-acetoxy-2(3H)-furanone, C22H32O6, was synthesised from andrographolide. It crystallizes in the orthorhombic system with a= 7.4219(12), b= 11.8411(10), c= 23.777(4) Å in space group P212121. While the stereochemical relation between rings is slightly changed from the starting material, acetylation of the hydroxyfuranone moiety completely abolishes O--H$$ \cdots $$O hydrogen bonding there, leaving a C--H$$ \cdots $$O interaction. The hydrogen-bonded chains at the opposite end of the andrographolide molecule persist but reverse direction.
Databáze: Supplemental Index