5-甲基-3-对甲苯基-2-对氯苯硫基-1H茚酮的合成及晶体结构  

Synthesis and Crystal Structure of 2-((4-chlorophenyl)thio)-5-methyl-3-(p-tolyl)-1H-inden-1-one

作　　者：刘长青[1] 樊建 袁明[1] LIU Changqing;FAN Jian;YUAN Ming(Bengbu Medical College,Department of Drug Synthesis,Anhui 233030,China;Anhui Academy of Science and Technology,Anhui,230088,China)

机构地区：[1]蚌埠医学院药物合成教研室,安徽蚌埠233030 [2]安徽省科学技术研究院,安徽合肥230088

出　　处：《合成化学》2022年第9期716-720,共5页Chinese Journal of Synthetic Chemistry

基　　金：安徽省高校自然科学研究重点项目(KJ2021A0708);安徽省生化药物工程技术研究中心开放课题(2022SYKFD02)。

摘　　要：单质碘与三苯基膦促进的对氯苯亚磺酸钠与1,3-二对甲苯基丙炔-1-醇的自由基加成-分子内氧化碳氢键环化的多步骤串联反应,以70%的产率得到化合物5-甲基-3-对甲苯基-2-对氯苯硫基-1H-茚酮。化合物经^(1)H NMR、^(13)C NMR、IR和HR-MS等表征,其结构经X-射线单晶衍射分析确证。晶体属于三斜晶系,空间群P-1,晶细胞参数:a=10.7305(7)Å,b=13.0234(8)Å,c=14.7071(9)Å,α=105.289(3)°,β=101.273(3)°,γ=98.623(3)°,V=1899.7(2)Å^(3),Z=4,Dc=1.318 mg/m^(3),μ=0.320 mm^(-1),F(000)=784。结构偏离因子R=0.0705,wR_(2)=0.1903,共收集到8687个独立衍射点,其中I>2σ(I)的可观测点为5542个。I-PPhmediated one-pot cascade reaction of 1,3-di-p-tolylprop-2-yn-1-ol and 4-chlorobenzene sodium sulfinate was studied and the title compound 2-((4-chlorophenyl)thio)-5-methyl-3-(p-tolyl)-1H-inden-1-one was conveniently supplied in 70%yields.The reaction may preed through radical addition-intramolecular oxidative C—H bond cyclization sequence.The compound was characterized by^(1)H NMR,^(13`)C NMR,IR and HRMS and the structure was determined by X-ray diffraction analysis.The crystal belongs to triclinic system,space group P-1 with a=10.7305(7)Å,b=13.0234(8)Å,c=14.7071(9)Å,α=105.289(3)°,β=101.273(3)°,γ=98.623(3)°,V=1899.7(2)Å^(3),Z=4,Dc=1.318 mg/m^(3),μ=0.320 mm^(-1),F(000)=784,the final R=0.0705,wR_(2)=0.1903 for 5542 observed reflections with I>2σ(I)in 8687 independent reflections.

关 键 词：对氯苯亚磺酸钠 硫代茚酮 晶体结构 串联环化 自由基加成 合成 

分 类 号：O625.72[理学—有机化学]