Synthesis, Crystal Structure and Antimicrobial Activity of(E)-2-(2-(4,8,8-Trimethyldecahydro-1,4-methanoazulen-9-ylidene)ethyl)benzo[d]isothiazol-3(2H)-one  

作　　者：LAN Hong-Yun HUO Shang-Chao HUANG Dao-Zhan LU Yu-zhou 蓝虹云;霍尚朝;黄道战;陆于州(College of Chemistry and Chemical Engineering,Guangxi University for Nationalities,Nanning 530008,China;Guangxi Key Laboratory of Chemistry and Engineering of Forest Products,Guangxi University for Nationalities,Nanning 530008,China)

机构地区：[1]College of Chemistry and Chemical Engineering,Guangxi University for Nationalities,Nanning 530008,China [2]Guangxi Key Laboratory of Chemistry and Engineering of Forest Products,Guangxi University for Nationalities,Nanning 530008,China

出　　处：《Chinese Journal of Structural Chemistry》2020年第8期1546-1552,1362,共8页结构化学（英文）

基　　金：Supported by the Natural Science Foundation of Guangxi Zhuang Autonomous Region(No.2017GXNSFAA198027);Special Fund for Innovation-driven Devlopment of Guangxi(GUIKE AA17204087-21);National Training Program of Innovation and Entrepreneurship for Undergraduates(201510608042)。

摘　　要：The title compound(E)-2-(2-(4,8,8-trimethyldecahydro-1,4-methanoazulen-9-ylidene)ethyl)benzo[d]isothiazol-3(2H)-one(Ic)was synthesized from longifolene and 1,2-benzoisothiazolinone(short as BIT)through Prins,halogenation and nitro-alkylation reaction and structurally identified by means of HRMS,IR,1H-NMR,13C-NMR and single-crystal X-ray diffraction.The crystal of compound Ic is of bi-molecular structure and belongs to orthorhombic system,P212121 space group with a=7.5715(7),b=16.8824(9),c=31.1926(14)?,V=3987.2(5)A^3,Mr=367.53,Dc=1.225 mg/m^3,Z=8,μ=0.174 mm^–1 and F(000)=1584.A total of 17045 reflections were collected,of which 7306 were unique(Rint=0.0566).The structure was refined to R=0.0967 and wR=0.1998 for 7306 observed reflections withⅠ>2σ(Ⅰ).1D chain along the a-axis is formed by two types ofπ-πinteractions between benzene rings from adjacent molecules.Especially,compound Ic shows improved solubility in nonpolar organic solvents and higher antimicrobial activity than longifolene and BIT against bacteria and fungi.The minimum inhibition concentration(MIC)of Ic against two Gram-positive bacteria(S.aureus and B.subtili),two Gram-negative bacteria(E.coli and K.pneumoniae)and three fungi(C.albicans,C.tropicalis and A.niger)are 0.242,0.242,15.6,15.6,1.95,1.95 and 1.95μg/mL,respectively.

关 键 词：LONGIFOLENE ω-chloromethyl longifolene 1 2-benzoisothiazolinone derivative crystal structure antimicrobial activity 

分 类 号：O626[理学—有机化学]