第一部分、萘醌衍生物应用於氧化还原开关之研究-

1、B萘醌Part I¡B Rational design of naphthoquinone-based derivatives aspotential redox switchesB×s q z×A l X G P q qA Q o q A w q a P M j z F w qa P_V M pÅA o i B tC X A P A P C A K i zL q A oÅCÅC z QU C G1¡n T°O¾AÅ(ON®AC O B2¡n C×B3¡C

2、 q B4¡C qq B5¡t B6¡n1Cp k O°Xl±(control unit¡A°s b P Bw A A¨p G A t (bistable system¡F H o¬ (active unit¡C m AD naphthoquinone »P dihydroxynaphthalene e oS2A L hl A p2003A Bittner3H H quinone stilbene X s A IÅé-¨Åt A Y v

3、°ªs t Apc p C BN -hydronaphthoquinone-stilbene systems³p zQuinone O n q l ÅA 4,5,6A b q y A P q l P 7,8A B v q A ÅX quinone-hydroquinone t C Stilbene E o A y g A l q l O I A O g stilbeneQ E o F quinone ÅC p A o stilbene Q s quinone ¤W¡A§ÎŦ

4、X stilbene-linked hydroquinones¡A K i H O h o C Chloro-naphthoquinone X Q A quinonic Q hydroquinonic Y j P A p G CNHClORN HClOHRG B N -hydroquinonyl aminostilbene¤H2005A Bittner9H i B X H2-chloro-1,4-naphthoquinone °DÅés l t°A b c W t°ò5-dimethylaminonaphthale

5、ne s D m piperazine¡C bÅU HX1s b A CuA hydroquinone j P X A p T: 12 T B H2-chloro-1,4-naphthoquinone °DÅé2004A Zhu10H X X tetrathiafulvalene¡TTF¡M anthracene DÅéA p Cu H G(1¥E o y q lphotoinduced electron transfer (PET A o q TTFÅ°AÅE o

6、 A Ao D-A X b e e X L z F(2 b A TTF Åq l IÅéO z A p PET N Q A PW j F(3 N TTF l TTFÅP z CTTF M TTF l°O i°fªA HO i°fªC34B TTF M anthracene DÅé B TTF q l IÅéX3W j A n a A3j i s q i f a C2006A Hummelen11H X anthraquinone°M °thioa

7、cetyl s l A i°fªq A g ql M A q mÅÜ°u m C o S Bb l q l m W A H anthraquinone°°òA°C O Q l b q lm A q°i°fªA p C B anthraquinone°M°thioacetyl s lW z l o j naphthoquinone¡B anthraquinone M tetrathiafulvalene°DÅéA m

8、j AÅ°Q s A X C G Qnaphthoquinone »P dihydroxynaphthalene e oS Ap X H naphthoquinone ¬°°òc bA Wj×CÅCL B s°Ênaphthoquinone »P dihydroxynaphthalene e oS Ap X H naphthoquinone ¬°°òcb A p C C 21114a R1 = Me , R2 = Meb R1 = Ph

9、 , R2 = Mec R1 = Ph , R2 = Phd R1 = Me, R2 = Phe R1 = Me, R2 = p-C6H4NMe2C B b N12t We j×CÅA Gp X11e¡A p C萘醌 N,N-¤G°i N°ò°o g°òA O WUV f max l i AÅCÅC K Bpt萘醌参11d A p E C 1.CH 3MgBr 2Op -TsOH O OO11d1 day10 minE B X 11d N o2-acetyl-1,3-inda

10、nedione ·J G J A b B D UJ AÅJ (diazomethane (¥N-N-vf i (diazald ²A C C aÅA1¤p A Y°A Q W h o X515C A5·A Aq A4¤A K i o X6¡C6¦b呋 (THF q JÅ15¤A l w J(methylmagnesium bromide solutionAJ M G A qL W h Y i o7¡C7·(1¡G1 A bÅU

11、J cerium(IV ammonium nitrate (CAN ÅÍA 15¤Y i o X8¡C A8·1-phenacylpyridinium bromide (13¡A q N2Å15¤A b50 J U C C w J T A°òi A1-2¤pÅA1¤A N i¥H±o¨ì²V¦Xª«9d©10d¡A¥u-n±N²V

12、6;Xª«·»©ó-f¤¤¡A¥¶Ê¤Æ¶qªºp-toluenesulfonic acid monohydrate (p-TsOH¡D H2O °j¬y A5-10¤A Y i o X11d16C¹wp X11a-e i H b A pC 11a R1 = Me , R2 = Meb R1 = Ph , R2 = Mec R1 = Ph , R2 = Phd R1 =Me ,

13、 R2 = Phe R1 =Me , R2 = p-C6H4NMe2142Q B X11a-eQ w k°»X11a-e A ocyclic votammograms¡A CV¡ÅãQ Q Co X11a-e o GÅl p A qO°11a-0.74V B-1.34V F11b -0.71V B-1.34V F11c -0.65V B-1.19V F 11d -0.69V¡B-1.31V¡F11e -0.76V¡B-1.34V¡A CV (ª±ob C-

14、1C-3m f A h qq11e C-3mN,N-dimethylaminobenzene¡A N°ò°f°òQ C Q B X11a b H tetrabutylammonium hexafluorophosphate°q F y t v°100 mV/sCV ¹ Q G B X11b CV Q T B X11c CV Q B X11d CV Q B X11e CVB 11a-e qXE 0M 1 (V E 0M 2 (V11a-0.74 -1.34 11b -0.71 -1.34 11c -0.65

15、 -1.19 11d -0.69 -1.31 11em A Q J G P N B u °q l A w N X 11a-d 14a-d¡A 14a-d A 11a-d¡C b p A u A b n l b t p C 11a R 1 = Me , R 2 = Me 11b R 1 = Ph , R 2 = Me 11c R 1 = Ph , R 2 = Ph 11d R 1 =Me , R 2 = Ph214a R 1 = Me , R 2 = Me 14b R 1 = Ph , R 2 = Me 14c R 1 = Ph , R 2 = Ph 14d R 1

16、 =Me , R 2 = PhQ B X 11a-d 14a-d CafterbeforeN X 11e H A u A b t p C C 11e 14e b UV i U g i X 11e A 萘醌 14e A naphthoquinone dihyroxynapthalene m A B C-3N , N -¤G °°o °òP A p Q C k C C 11e 14e C ¥UV l A X 11a b u c C b u A fmax = 485 nm¡A C beforebeforeafterafter

17、76;F b N B u°ÑP A i485 nm l mÅX t l W A i 389 nm¡A C°A c TÅC L X11a-epC A l i C Q K B X11a e UV l Q E B X11b e UV l G Q B X11c e UV l G Q B X11d e UV l G Q G B X11e e UV lG B X11a-e14a-e UV l i Cpd max (nm log Cpdmax (nm log UV l o A X11a-e c A CA11a-eC t14e l q l vf A

18、p G Q T C q l v w q°l o gl P l l C o X14e b gE o i478 nm A g i°594 nm A q l v°0.07¡AExcitationEmissionWavelength E m i s s i o nF X 14e g CG Q T B X 14ev B×b A Q naphthoquinone ³p X H B X b X10d¡A v 50%CÅA b A X10d A H u A10d A A g2,3-Dichloro-5,6-dicyano-1,4b

19、enzoquinone (DDQ®A CÅA z L UV l X10dA B Q CV o10d q q A10d i f CBÅB1.I w MEL-TEMP¢I w AÅ×g C2.u1725XFT-IR (Fourier Transform Infrared ¬uC GÅé (KBr ÆQ w A TÅéV X w A°i (cm-1¡A C X S w lp C3.C R(Low resolution mass spectroscopy 

20、4;°R(High resolution mass, HRMS ©e°U°ê_Q NA JOEL JMS-SX/SX 102A C4.X g A e°U°êQ N A BruderAXS SMART-1000g b l T cŲwc R C5.B Varian Unity 300 (300 MHz solars systemAVarian Unity 300 (75 MHz solars system¡C(CDCl3¡B J(methanol-d6 °A H

21、76;J (tetramethylsilane ¬°° (internal standardC Hppm°A J N (coupling constant¡A°Hz¡C (splitting pattern ©w q p U G s p (singlet¡F d p (doublet¡F t T p (triplet¡F m h p (multiplet¡C 6.h W (Column chromatography ¨w°êq J t (E.Me

22、rck Silica gel 60 (230-400 mesh C7.h h (Thin layer chromatography ¨w°êq J tSilica gel 60 F254h h C Q O (UV light ªH 5 %ÁC (phosphomolybdic acid ¤A J GQÅx¦b h h W AÅC8.BÜCHI R114°j±o M SIBATA WJ-20yAÅU uÅ×°25 mmHg¡C9

23、.X F u(TCIB°Fisher B°Lancaster B°Aldrich Janssen t CB R p T A°òi B J B A J B v J BA AB G J°h RÅA°Tedia t C°g S O A J C10.§l×w°w q HP 8453A B 1cm cell¡A A H n i I C11.¿g q q l v pg O HITACHI F-4500 fluorescencespectrophotometer w A

24、 B 1 cm ® cell ; ¤X 14e q l v Coumarin 6 (f =0.82, max = 458 nm in EtOH¡A q l v O X14e Coumarin 6b P l×A P E o i u U n Aq l v L g v A p p U C F¡G n A¡G l l×n¡G g vf G q l vsolvent-1: solvent-2: ¼a: s:12. ´w R O Q PAR Model 273A ¹q RA T O°qA

25、g/AgCl M KClTBAPF6tetrabutylammonium hexafluorophosphate¡°qq O q X11a-e C y q db-1.85¡0.0V A y t v°100 mV/sec¡AG H G ZÅK¡ferrocene¡°I°A w R mÅãG Q C ¹G Q B w q mG B X X2-Acetyl-4-methoxy-1-naphthol (5132-Acdetyl-1,3-indanedione (100 mg

26、¡A 0.53 mmol 10 mL G J A b B D C C J J(Diazomethane¡A N ÅA 1p Y °A QW h (2% EtOAc/hexanes ±o H T ÅéA v 40% ; R f =0.42 (10% EtOAc/hexanes ; mp 116-117 ¢J (lit.,13mp 115-116 ¢J ; 1H NMR (CDCl 3, 300 MHz 13.75 (s, 1H, OH, 8.45 (d, J = 8.3 Hz, 1H, ArH, 8.19

27、(d, J = 8.3 Hz, 1H, ArH, 7.69-7.55 (m, 2H, ArH, 6.80 (s, 1H, ArH, 3.97 (s, 3H, OCH 3, 2.67 (s, 3H, CH 3.2-Acetyl-1,4-dimethoxynaphthalene (613N X 5 (1 g¡A 4.62 mmol ·J 100 mLA J °®L (1.6 g¡A 11.56 mmol ÅÍAA J L q °K (¬ 2 mL¡A ÅU 4A A G J A pH A

28、h H L °B Y A Q W h (4% EtOAc/hexanes o GÅéA v 90% ; R f = 0.28 (10% EtOAc/hexanes; 1H NMR (CDCl 3, 300MHz 8.26-8.21 (m, 1H, ArH, 8.18-8.12 (m, 1H, ArH, 7.60-7.55 (m, 2H, ArH, 7.08 (s, 1H, ArH, 3.99 (s, 3H, OCH 3, 3.94 (s, 3H, OCH 3,OH OCH 3OOCH 33O2.80 (s, 3H, CH 3.3-(1-Hydroxy-1,1-di

29、methyl-1,4-dimethoxynaphthalene (7136 (100 mg¡A 0.43 mmol °L THF ÅA q J N 215A b ÅU C C w J L q methylmagnesium bromide solution (1 mL¡A JM G ATHF¡A G J A pH A h H L °B Y A Q W h(8% EtOAc/hexanes ±o H G ÅéA v 80% ; R f = 0.44 (30% EtOAc/hexanes ; 1H

30、NMR (CDCl 3, 300 MHz 8.24-8.21 (m, 1H, ArH, 8.01-7.98 (m, 1H, ArH, 7.55-7.46 (m, 2H, ArH, 6.78 (s, 1H, ArH, 4.92 (s, 1H, -OH, 4.01 (s, 3H, OCH 3, 3.99 (s, 3H, OCH 3, 1.72 (s, 6H, CH 3.3-(1-Hydroxy-1,1-dimethyl-1,4-naphthoquinone (8137 (100 mg¡A 0.463mmol J M (1¡G 1 A b ÅU ÅÍ

31、J Cerium(IV ammoniumnitrate (CAN (710 mg¡A 1.29 mmol¡A A A ÅApH A h H L °B Y A Q W h (8% EtOAc/hexanes o H T ÅéA v¬72% ; R f = 0.40 (15% EtOAc/hexanes ; mp 84-85 ¢J ; 1H NMR (CDCl 3, 300 MHz 3OCH 3OHO OH 8.13-8.05 (m, 2H, ArH, 7.80-7.73 (m, 2H, ArH, 6.97 (s, 1

32、H, CH, 3.37 (s, 1H, OH, 1.61 (s, 6H, CH 3.1,1-Dimethyl-3-phenyl-1H -naphtho2,3-c -pyrane-5,10-dione (11d8 (100 mg A 0.46 mmolmmol¡A q N 2 Å15A b50 J U C C w J T A °òi(46.8mg¡A 0.46 mmol¡A 1-2p ÅA1A A G J A 0.2 N Q GpH 2.0¡A h H L °B Y C A N o f(10 mL¤

33、;A M q p -TsOH D H 2O °j¬y A5-10A A G J A h H L °B Y A Q W h(2% EtOAc/hexanes o T ÅéA v 95%¡F R f = 0.58 (15% EtOAc/hexanes ; Mp 105-107 o C. 1H NMR (CDCl 3, 300 MHz 8.09-8.03 (m, 2H, 7.83-7.80 (m, 2H, 7.72-7.67 (m, 2H, 7.44-7.42 (m, 3H, 6.71 (s, 1H, 1.84 (s, 6H. 13C NM

34、R (CDCl 3, 75 MHz 183.1, 181.8, 159.2, 137.4, 134.0, 133.5, 133.4, 132.7, 131.3, 130.6, 128.5, 126.0, 92.3, 80.1, 26.4. HRMS (EI m /z calcd for C 21H 16O 3 316.1099, O OOfound 316.1093 (M+. IR (KBr 2925, 1665 (C=O, 1642 (C=O, 1538, 1389, 1305, 709 cm-1°B°Ñm1.Westermeier, C.; Gallmeier

35、, H. C.; Komma, M.; Daub, J. Chem.Commun., 1999, 23, 2427-2428.2.Marchand, A. P.; Reddy, G. M. Synthesis1991, 3, 198-200.3.Sutovsky, Y.; Likhtenshtein, G. I.; Bittner, S. Tetrahedron2003, 59,2939-2945.4.Waldeck, D. H. Chem. Rev. 1991, 91, 415-436.5.Saltiel, J.; Waller, A. S.; Sears, D. F. J. J. Am.

36、Chem. Soc. 1993, 115,2453-2465.6.Papper, V.; Likhtenshtein, G. I.; Medvedeva, N.; Khoudyakov, D. V.J. Photochem. Photobiol. A1999, 122, 79-85.7.Ghosh, H. N.; Pal, H.; Palit, D. K.; Mukherjee, T.; Mittal, J. P.J.Photochem. Photobiol. A1993, 73, 17-22.8.Higashida, S.; Tsue, H.; Suguira, K.; Kaheda, T.

37、; Sakata, Y.; Tanaka,Y.; Taniguchi, S.; Okada, T. Bull. Chem. Soc. Jpn. 1996, 69, 1329-1335.9.Bittner, S.; Illos, R. A.; Harlev, E. Tetrahedron Lett. 2005, 46,8427-8430.10.Zhu, D.; Zhang, D.; Zhang, G.; Guo, X. Org. Lett.2004, 6,1209-1212.11.Van Dijk, E. H.; Myles, D. J. T.; Van der Veen, M. H.; Hum

38、melen, J.C. Org. Lett.2006, 8, 2333-2336.12.X11a-c¥11e¬C13.P A E Q A F s hC14. ³A E Q A F s hC15.(a A. A. Akhrem, F. A. Lakhvich, N. A. Filchenkov, Russ. J.Org.Chem. 1979, 15, 2333-2337; (b Y. S. Chen, P. Y. Kuo, T. L.Shie, D.Y. Yang, Tetrahedron 2006, 62, 9410-9416.16. T. Nguyen Van,

39、 B. Kesteleyn, N. De Kimpe, Tetrahedron 2001,57,42134219. G B h(MCRs¦X XPart II. MCRs synthesis of oxazatetracycles as potential fluorescence redox switchesB ×o i t U X k B P A O X b h X j h H B J B J X i c A b P L K y A y A z Q X p 1A B wB °ªv B °ªv P u O u q X k C one

40、 pot100% yieldready available starting materialstotalenvironmentallyfriendlyB z Q Xh (multi-component reactions, MCRs§°n X t B n v B °ªv H b o u I z Q X S C MCRs w q °u O T H W °_©l A t °_©l c v A MCRs H T °_©l A b L i h °P A H P °P A

41、i l B l B O Y X A o k P i C MCRs b one pot S P b C X B J nP A MCRs Y u P g u I CMCRs A T (¹G2A I A b Ci f A l b A A A H l A y x C II A i A i f b i f A A i H o h A A III A b C i f A n H n v A H W MCRs T G BMCRMCRs¦b X W w h o A 2004¦Sonoda 3o H B Mepoxides¦X 1,3-oxathiolan-2-ones(

42、¹T¥H 2004¦Quirion¥HMCRs¦X ,-difluoro-£-aminoacids 4(¹¤W z X d HMCRsªY u X P °v A Ån o H MCRs§t X CO+SCONaH THFSOO98% T B H MCRs¦X 1,3-oxathiolan-2-ones +R1NH2R R1B H MCRs¦X,£-difluoro-£-aminoacids¦b2004Sames5o H

43、6;DÅé°w¤X4¡Ap z p A EDG N q l°òF EWG N q l°òAX4A H“push-pull” fluorophore s b A t q l°òPq l°òA q l°ò° q l J°ò“push-push” fluorophore CO OON4B°w¤X4p z2006Ohwada6o l i°PX5¡A5l g(¹A b D l

44、v q l v(F¤p0.0003¡A bl G J q l v°0.21¡Crt, 14 hMeO OMeO5nonfluorescence in aprotic solvent(ex. n-Hexanestrongly fluorescence in protic solvent(ex. MeOHB X5yL B s °ÊÅe H naphthoquinone 7 D A j A z naphthoquinone »Pdihydroxynaphthalene 8-10 e o S A naphthoquinon

45、e °A P O g C Åo H °D ÅéA °s A (¹C11A D n o °7-¤G °-4-m °òA 4m W m °òQ °A °D n h o A b o P A °D ÅéA O i °fªP G A I b L k b A A A B w A C O O OSN 61234C B X 6e ce A X B J B v C A H o H s k A h (MCR

46、s¨°X v P v Ai o p H P z A b i A P A A w A p H T X °b A °A °B °l (¹K ¡C b L h s P o o i H °µ°n o A b X T X °l A Nt o A b P U A 4m W m °òB QP a t q A g q ICT(intramolecular chargetransfer¡A o j ×U °p E C Q T X T GOOO

47、N N close formopen form strongly fluorescentweakly fluorescentHK B H °D Åép T X °b XO OH NOO ONOEt 3NHEt 3N MeOH123489strongly fluorescentweakly fluorescent E B o PO OO N NOOHO NON IOOH OOOHNIQ B X T X°ÑB G P °Q½×HMCR p P X T X D ÅéA T X D n T G

48、 K Q B P A X y H Q °A N K Q P H J T A °òi °µ°P A °j¬y K p Y i o T X C b P U i m J (enolization¡Aenolate A P 2-¥°K Q i aza-Diels-Alder¡e 4+2¡f12A P i Y o T X C X H Q G C G Type III MCRs¡CNCH 3II10aQ B T X XyBenzene,refluxNCH 3INIO

49、OHO OOO N 10aNN6refluxQ G B X T X cT t C X T B M v F G 2-¥°K Q B2-¤A °òK Q B 1,2-¤G °K Q B2,3-G °K Q A G H h X A T G 4-ßm °òB7-¤G °i -4-ßm °òP 5,5-¤G °-1-ßm °ò-3-Àv CB X 10a10j XGTcv10aNIO O

50、HON93%10bNIOO OHOON82%10cNIOOHO65%10dNIO OHON90%10eNIO OHOON81%10fNIOHO62%10gNIO OHONO90%10hNIO OHOON83%10iNIOHOO64%10jNIO OHONO91%t C X H10a¡10b¡A10d¡10e¡A10g¡10h10j i H o n v A b10a¡10d¡10g10j10b¡10e 10h D n t b4-ßm°òM7-¤G°i-4-ß

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