摘要
首先,以(L)-(+)-酒石酸和(L)-天冬氨酸、(L)-谷氨酸、(L)-脯氨酸、(L)-苯丙氨酸以及(L)-酪氨酸等氨基酸为反应底物,分别与几种低级脂肪醇和邻苯二胺反应,合成了(1R,2R)-二(2-苯并咪唑)乙二醇(BBImED)、(1S),2-二(2-苯并咪唑)乙胺(BBImEA)以及(1S),3-二(2-苯并咪唑)-1-丙胺(BBImPA)等几种具有光学活性的二元苯并咪唑类化合物,还有(L)-脯氨酸乙酯(PEE)、(L)-苯丙氨酸乙酯(PAEE)、(L)-苯丙氨酸异丁酯盐酸盐(PAiPE·HCl)、(L)-苯丙氨酸正丁酯(PAnBE)、(L)-酪氨酸甲酯(TME)和(L)-酪氨酸乙酯(TEE)等几个氨基酸酯类衍生物以及一种新的化合物——(1S)-(2-苯并咪唑)-2-(对-羟基苯基)乙胺(BImpHPEA),并通过元素分析、红外光谱、氢核磁共振谱以及旋光度等对这些化合物进行表征。
其次,首次以(L)-(–)-α-苯乙胺、(L)-脯氨酸和(L)-酪氨酸为手性诱导剂,以CuCl_2·2H_2O和FeCl_3·6H_2O为催化剂,在几种反应介质(包括水及其它的一些有机溶剂)中氧化偶合2-萘酚,合成了光学活性的BINOL。当(L)-酪氨酸作为手性诱导剂,CuCl_2·2H_2O作为催化剂,9:1(体积比)的乙醇溶液作为反应介质时,化学产率可达79%,同时光学产率(e.e.值)可达49.4%。根据(L)-(–)-α-苯乙胺和铜(II)催化剂存在条件下不同反应介质中2-萘酚氧化偶合反应的结果,讨论了反应介质对化学产率和光学产率的影响,确定了2-萘酚的氧化偶合反应为离子型反应。另外,根据所得产物的立体构型,进一步提出了可能的反应机理。
再次,由光学活性氨基酸类衍生物和一些过渡金属无机盐,如CuCl、CuCl_2·2H_2O、FeCl_3·6H_2O以及CoCl_2等,首次合成了几种手性过渡金属络合物,并在有机溶剂中催化氧化偶合2-萘酚,制得了光学活性的BINOL。结果表明:由(L)-酪氨酸乙酯和CuCl_2·2H_2O制备而得的络合物CuCl_2–TEE与由(1S)-(2-苯并咪唑)-2-(对-羟基苯基)乙胺(BImpHPEA)和CuCl制备而得的络合物CuCl–BImpHPEA的催化效果较好,化学产率分别达到67%和72.6%,光学产率(e.e.值)分别达到62.1%和53.9%,而由(L)-苯丙氨酸乙酯和无水CuCl2制备而得的络合物CuCl2–PAEE的催化活性相对稍低,化学产率和光学产率(e.e.值)分别为22.4%和44.5%。
还合成了N,N,N,’N’-四苄基乙二胺(TEBDA)及其铜(II)络合物二(桥-氯)-二[氯(N,N,N’-三苄基乙二胺)铜(II)](Cu–TriBEDA),通过元素分析、红外光谱、氢核磁共振谱以及X-射线单晶衍射等表征了这两种化合物。Cu–TriBEDA络合物分子为Cu二聚化合物,且每个晶胞中含有两个相似但在晶体学上相互独立的Cu二聚单元。此外,以Cu–TriBEDA为催化剂、空气为氧化剂制备了外消旋的BINOL。
在少量外消旋BINOL和NaOH存在条件下,以K_2S_2O_8为引发剂,以丙烯酸为反应单体,采用传统的自由基溶液聚合方法在水溶液中首次制备了BINOL交联的聚丙烯酸树脂,并通过红外光谱对所得产物进行表征。当反应体系中存在外消旋的BINOL时,自由基聚合反应仍能顺利完成,这表明:虽然BINOL为酚类化合物,但是它不能作为聚合反应的阻聚剂;相反地,在丙烯酸聚合反应过程中,它可以起到交联作用。通过进一步对BINOL交联的聚丙烯酸树脂吸水性能的测定,结果表明BINOL交联的聚丙烯酸树脂作为高吸水性树脂具有一定的应用价值。
以对苯二酚、2-萘酚、吗啉和哌啶以及甲醛或多聚甲醛为反应底物,通过酚类化合物的区域选择性Mannich胺甲基化反应,首次了合成了几种Mannich碱,通过对反应机理的研究,比较了经典Mannich反应与改进的Mannich反应之间的异同点。
最后,合成了一系列含有7,7,8,8-四腈基对苯醌二甲烷(TCNQ)的稀土金属络合物Ln(phen)_4(TCNQ)_4(H_2O),通过熔点、红外光谱和元素分析等对它们进行了表征,并测定了室温下七种Ln(phen)_4(TCNQ)_4(H_2O)络合物的磁学性能以及Nd(phen)_4(TCNQ)_4(H_2O)络合物低温条件下的磁学性能。实验结果表明:无论是在室温条件下还是在低温条件下,Ln(phen)_4(TCNQ)_4(H_2O)络合物均为顺磁性化合物。
Firstly, several chiral bibenzimidazole compounds and several chiral amino acidderivatives, (1R,2R)-bis(1-H-benzimdazol-2-yl)ethane-1,2-diol (BBImED),(1S),2-bis-(1-H-benzimidazol-2-yl)ethylamine (BBImEA),(1S),3-bis-(1-H-benzimdazol-2-yl)-1-propylamine (BBImPA), (L)-proline ethyl ester(PEE), (L)-phenylalanine ethyl ester (PAEE), (L)-phenylalanine iso-propyl esterhydrochloride (PAiPE·HCl), (L)-phenylalanine n-butyl ester (PAnBE), (L)-tyrosinemethyl ester (TME), (L)-tyrosine ethyl ester (TEE), and a new optically activecompound, (1S)-(1-H-benzimidazol-2-yl)-2-(p-hydroxyphenyl)ethylamine(BImpHPEA), are synthesizedby the reaction of(L)-tartaric acid,(L)-aspartic acid,(L)-glutamic acid, (L)-proline, (L)-phenylalanine, (L)-tyrosine as substrates withseveral low-molecular-weight aliphatic alcohols and o-phenylenediamino,respectively. These compounds are characterized by IR spectra, 1H NMR spectra,elementalanalysesandopticalactivity.
Secondly, optically active 1,1’-bi-2-naphthol is prepared by the oxidativecoupling of 2-naphthol with (L)-(–)-α-phenylethylamine, (L)-proline and (L)-tyrolineas chiral inducing agents, and CuCl_2·2H_2O and FeCl_3·6H_2O as catalysts in severalkinds ofreaction media including water and other organic solvents for the first time.Optically active 1,1’-bi-2-naphthol is obtained with the yield of 79% and e.e. of49.4% when (L)-tyroline is used as chiral inducing agent, CuCl_2·2H_2O is used ascatalyst,and9:1(V/V) ethanolsolutionisusedas reactionmedium.Accordingtotheexperimental results ofoxidative coupling of 2-naphthol in several different reactionmedia in the presence of (L)-(–)-α-phenylethylamine and Cu(II) catalyst, we discussthe influence of reaction medium on the yield and e.e., and draw a conclusion thatoxidative coupling of 2-naphthol holds the characteristic of ion-type reaction. Inaddition, we propose a possible reaction mechanism for oxidative coupling of2-naphthol through the analysis of the configuration of the optically active productsfromtheviewpointofstereochemistry.
Furthermor, several kinds of chiral transition metal complexes, which canoxidize catalytically 2-naphthol to yield optically active 1,1’-bi-2-naphthol in someorganic solvent, are synthesizedfor the first time from the corresponding derivativesofchiral amino acidand some transition metal salts, for example, CuCl, CuCl_2·2H_2O,FeCl_3·6H_2O,CoCl_2 and so on.The data show that the catalytic activity of CuCl_2–TEEcomplex, derived from (L)-tyrosine methyl ester and CuCl_2·2H_2O, andCuCl–BImpHPEA complex, derived from(1S)-(1-H-benzimidazol-2-yl)-2-(p-hydroxyphenyl)ethylamine and CuCl, are ratherhigh, and the yields are 67% and 72.6%, respectively, and e.e. are 62.1%and 53.9%,respectively. But the catalytic activity of CuCl_2–PAEE complex, prepared from(L)-phenylalanine ethyl ester and anhydrous CuCl_2, is relatively low and gives theyield of 22.4% with 44.5%e.e..
N,N,N’,N’-tetrabenzylethylenediamine (TBEDA) and its corresponding Cu(II)complex, bis(μ-chloro)-bis[chloro(N,N,N’-trisbenzylethylenediamine)copper(II)](Cu–TriBEDA), which comprises two similar but crystallographically independentdimeric units in crystal cell, are parpared and characterized byelemental analyses,IRspectra, ~1H NMR spectra and single-crystal X-ray diffraction. Forthermore, racemicBINOL is synthesized via oxidative coupling of 2-naphthol with Cu–TriBEDAcomplex as catalyst and molecular oxygen as oxidant.
In the presence of a few amount of racemic BINOL and NaOH,BINOL-crosslinked polyacrylic acid hydrogels are prepared for the first time viafree-radical solution polymerization in water solution with K_2S_2O_8 system as initiatorand acrylic acid as monomer, and the resulting product is characterized by IRspectrum. When there is BINOL in the reaction system, free-radical polymerizationstill proceeds completely, which indicates that although being a phenol compounds,BINOL is not an efficient polymerization inhibitor, on the contrary, it can beemployed as a crosslinking agent in the polymerization of acrylic acid. The furtherstudy on the water absorbency of BINOL-crosslinked polyacrylic acid hydrogelshows that it is an efficient superabsorbent and can find a certain application in theindustry.
Several versatile Mannich bases are synthesized by the regioselectiveMannich-type aminomethylation of phenol compounds such as hydroquinone and2-naphthol with morpholine, piperidine and formaldehyde (or polyformaldehyde).The corresponding reaction mechanism is proposed and the similarities anddifferences between the classical Mannich reaction and the modified Mannichreaction are summarized by the comparison between them.
Finally, A family of rare earth metal complexes containing7,7,8,8-tetracyanoquinodimethane (TCNQ), Ln(phen)_4(TCNQ)_4(H_2O), are preparedand characterized by melting point, IR spectra and elemental analysis. Moreover,magnetic properties of all of Ln(phen)_4(TCNQ)_4(H_2O) complexes at roomtemperature (298 K) and Nd(phen)_4(TCNQ)_4(H_2O) complex at low temperature (5 K)are measured. The experimental results indicate that all of thoseLn(phen)_4(TCNQ)_4(H_2O) complexes are paramagnetic materials both at roomtemperature(298K)andatlowtemperature(5K).
引文
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