Theoretical　studies　on　predicting　potential　reactive　sites　of　attractive　compounds　are　of　significance,　which　are　capable　of　providing　deeper　insight　into　their　chemical　behaviors　as　well　as　foundations　for　discovering　new　drug　molecules.　The　3,9-diazatetraasterane　derivatives　are　a　kind　of　cage　compounds　equipping　with　potent　biological　activities.　In　this　paper,　predication　of　reactive　sites　of　3,9-diazatetraasteranes　bearing　phenyl　and　ester　groups　(6,12-diphenyl-3,9-diazahexacyclo[6.4.0.0(2.7).0(4.11).0(5.10)]-dodecane-1,5,7,11-tetracarboxylate)　was　carried　out　by　the　conceptual　density　functional　theory.　Firstly,　a　conformational　search　of　3,9-diazatetraasterane　was　performed　by　molecular　dynamics　simulations　associating　with　Quantum　Mechanics　calculations　in　order　to　obtain　relative　stable　conformers.　And　then　the　reactive　site　prediction　of　3,9-diazatetraasterane　was　carried　out　by　the　Fukui　function　and　condensed　Fukui　function.　The　results　exhibited　that　the　potentially　chemical　reactive　site　is　the　N　atom　of　3,9-diazatetraasterane　scaffold,　which　is　readily　attacked　by　electrophilic　agent.　Meanwhile,　the　calculated　results　were　validated　by　experimental　outcomes　in　the　derivation　of　3,9-diazatetraasteranes.