以多組成反應合成多取代環戊烯及靛紅衍生物之方法探討

Abstract

三級膦的化合物與不對稱烯炔和苯亞甲基丙二腈進行一鍋化的反應，三級膦會優先攻打參鍵上的alpha位，共振產生一delta位帶負電荷的兩性離子，之後進行環化反應，形成三組成反應的產物。經過氫譜、碳譜、磷譜、紅外線光譜、質譜和單晶繞射的鑑定，則可驗證出此結構帶有伊立德結構，為了提升對這類多組成反應的產率及探討其取代基的影響，嘗試著使用不同的反應條件與改變不同的反應物取代基。另一方面，利用靛紅、對稱雙炔、三級膦和水的一鍋化反應，三級膦先打在對稱雙炔的alpha位，共振產生一delta位帶負電荷的兩性離子，接著對靛紅親核攻擊，再由醋酸水溶液中止反應，可得到四組成反應的產物。由於許多的天然物都含有為靛紅其骨架，因此這類的合成策略將可應用在天然物的合成上。

In this study, we used phosphine, (E)-dimethyl hex-2-en-4-ynedioate and benzylidenemalononitrile to obtain the dicyanocyclopentene bearing ylide functionality. We characterized these products by 1H, 13C, 31P, IR, Mass and X-ray diffraction analyses. These readily available structures may be adventageous to the total synthesis of molecules having this moiety. The other study, We obtained isatin- derivative bearing -ylide in one pot and characterized them by NMR, IR, MS and X-ray diffraction analyses. To optimize and discuss the effects substituent effects, we study reactions under different conditions and replace different reactants in this four-component reactions. Such synthetic methodology can be used to synthesize nature products because lots of nature compounds bear isatin skeleton.