化学酶法催化仲醇的动态动力学拆分
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摘要
本文对仲醇的动态动力学拆分(DKR)进行了研究,重点研究了固体酸催化剂的消旋催化性能及其与脂肪酶耦合在1-苯乙醇及其衍生物的DKR反应体系的应用,取得了以下成果：
通过对树脂的筛选,获得了两种催化消旋性能良好的酸性树脂CD550和CD8604,于40℃下能将(S)-1-苯乙醇完全消旋。进一步研究发现,两种树脂均具有强酸性功能基团和丰富的孔道结构,强酸性功能基团保证了其催化消旋的能力,丰富的孔道结构大大的增加了催化剂比表面积,保证了其高效的催化效率。
构建了一个高效的1-苯乙醇的DKR反应体系,采用一系列芳香酚(或醇)的乙酸酯取代简单的乙酸乙烯酯和乙酸异丙烯酯作为酰基供体,有效地抑制了树脂催化的转酯化副反应,大大提高了1-苯乙醇DKR反应的结果,获得了高产率和高ee值的产物。在这些酰基供体中,尤以邻苯二酚二乙酸酯、间苯二酚二乙酸酯以及3,5-二甲基苯酚乙酸酯这三种表现最为突出。CD550树脂(底物浓度100mmol/L):以邻苯二酚二乙酸酯为酰基供体时,反应10h,转化率大于99%,eep为90.5%；以间苯二酚二乙酸酯为酰基供体时,反应24h,转化率大于99%,eep为91.9%；以3,5-二甲基苯酚乙酸酯为酰基供体时,反应24h,转化率95.3%,eeP为87.3%。CD8604树脂(底物浓度100mmol/L):以邻苯二酚二乙酸酯为酰基供体时,反应3h,转化率96.2%,ee_P,达93.2%；以间苯二酚二乙酸酯为酰基供体时,反应24h,转化率为>99%,ee_P,为95.8%；以3,5-二甲基苯酚乙酸酯为酰基供体时,反应8h,转化率>99%,ee_P达91.5%。
进一步对反应底物的范围进行了拓展,均取得不错的结果,发现带有给电子基团的结构优于带有吸电子基团,邻位带有取代基的反应速度稍慢。以3,5-二甲基苯乙醇的DKR为例(底物浓度100mmol/L),该DKR的最适酰基供体为4-氯苯酚乙酸酯,以CD550为消旋催化剂时,反应24h,底物转化完全,产物ee值为97.4%；以CD8604为消旋催化剂时,反应3h,底物转化完全,产物ee值为96.5%。
鉴于树脂优异的消旋化催化性能,进一步制备了具有类似功能基团的固体超强酸Fe_2O_3/SO_4~(2-)催化剂,该催化剂具备良好的催化消旋能力,同时完全不溶于有机溶剂,可以耦合脂肪酶催化仲醇的DKR反应。
成功构建了固体超强酸Fe_2O_3/SO_4~(2-)耦合脂肪酶催化1-苯乙醇的DKR反应体系。当采用乙酸4-氯乙酸苯酯为酰基供体参与反应时(底物浓度100mmol/L),反应3h,底物转化率>99%,产物ee值为95.4%；采用乙酸3,5-二甲基苯酯为酰基供体参与反应时,反应12h,转化率达到90.5%,产物ee值为95.1%。
以固体超强酸Fe_2O_3/SO_4~(2-)作为消旋催化剂的DKR反应体系具有一定的适用范围,应用于多种芳香仲醇均取得不错的结果。以3,5-二甲基苯乙醇的DKR为例(底物浓度100mmol/L),该DKR的最适酰基供体仍为4-氯苯酚乙酸酯,反应3h,底物转化率>99%,产物ee值为93.7%。
利用酶促选择性醇解反应拆分消旋(RS)-炔丙醇酮乙酸酯制备获得高光学纯度的(R)-炔丙醇酮和(S)-炔丙醇酮乙酸酯,奠定了(RS)-炔丙醇酮的动态动力学拆分的酶学基础,同时对产物(R)-炔丙醇酮的消旋进行了研究。
In this paper, two kinds of acid catalysts were chosen as racemization catalysts and the catalytic performance were investigated. And the two kinds of acid catalysts could be applied to the DKR of several secondary aromatic alcohols successfully. The main conclusions were as follows:
Two acid resins with highly efficient racemization activity were screened and showed great potential to apply to the DKR of secondary aromatic alcohols. They could racemize (S)-1-phenylethanol almost completely in 6.5h at 40℃.
A series of phenyl acetate derivatives were synthesized and investigated for increasing the eep. And the selectivity of the DKR of 1-phenylethanol really could be successfully enhanced by using more complex acyl donors to inhibit the acid resin-catalyzed transesterification. When 1,3-Diacetoxybenzene and CD 8604 was used as acyl donor and racemization catalyst respectively, good yield (>99%) and high ee value of product (95.8%) were obtained. Good results were also obtained when 1,2-Diacetoxybenzene and 3,5-dimethyl phenyl acetate as acyl donors.
To expand the application area of the results, several substrates with different substitution groups on its benzene ring were tested and most DKR of them were performed successfully. For 1-(3,5-dimethylphenyl)ethanol, when 4-chlorophenyl acetate and CD 550 was used as acyl donor and racemization catalyst respectively, the product with 97.4%ee could be obtained in nearly 99% yield. When CD8604was used as racemization catalyst, the ee value of product was 96.5% with nearly the same yield as CD550.
Solid superacid Fe2O3/SO42- was prepared as racemization catalyst with excellent racemization capacity and also showed great potential to apply to DKR of several secondary aromatic alcohols.
The DKR of 1-phenylethanol catalyzed by lipase Novozym435-solid superacid Fe2O3/SO42- combo was established successfully, when 4-chlorophenyl acetate as acyl donor, good yield (>99%) and high ee value of product (95.4%) were obtained after 3h's reaction. While 3,5-dimethyl phenyl acetate as acyl donor, the yield and ee value of product was 90.5% and 95.1% respectively after 12h's reaction.
The Novozym435-solid superacid Fe2OSO42- combo catalyzed DKR system was also suitable for several secondary aromatic alcohols. For different substrates, appropriate acyl donor that gave good result was different. For DKR of 1-(3,5-dimethylphenyl)ethanol, the appropriate acyl donor was still 4-chlorophenyl acetate. After 3h's reaction, the yield and ee value of product was>99% and 93.7% respectively.
(RS)-4-hydroxy-3-methyl-2-(2'-propynyl)-2-cyclopentenone acetate was successfully resoluted by lipase-catalyzed alcoholysis through adjusting the basicity of organic reaction system, and the product was obtained in both high conversion and ee value. This information made good preparation for the DKR of (RS)-4-hydroxy-3-methyl-2-(2'-propynyl)-2-cyclopentenone.
通过对树脂的筛选,获得了两种催化消旋性能良好的酸性树脂CD550和CD8604,于40℃下能将(S)-1-苯乙醇完全消旋。进一步研究发现,两种树脂均具有强酸性功能基团和丰富的孔道结构,强酸性功能基团保证了其催化消旋的能力,丰富的孔道结构大大的增加了催化剂比表面积,保证了其高效的催化效率。
构建了一个高效的1-苯乙醇的DKR反应体系,采用一系列芳香酚(或醇)的乙酸酯取代简单的乙酸乙烯酯和乙酸异丙烯酯作为酰基供体,有效地抑制了树脂催化的转酯化副反应,大大提高了1-苯乙醇DKR反应的结果,获得了高产率和高ee值的产物。在这些酰基供体中,尤以邻苯二酚二乙酸酯、间苯二酚二乙酸酯以及3,5-二甲基苯酚乙酸酯这三种表现最为突出。CD550树脂(底物浓度100mmol/L):以邻苯二酚二乙酸酯为酰基供体时,反应10h,转化率大于99%,eep为90.5%；以间苯二酚二乙酸酯为酰基供体时,反应24h,转化率大于99%,eep为91.9%；以3,5-二甲基苯酚乙酸酯为酰基供体时,反应24h,转化率95.3%,eeP为87.3%。CD8604树脂(底物浓度100mmol/L):以邻苯二酚二乙酸酯为酰基供体时,反应3h,转化率96.2%,ee_P,达93.2%；以间苯二酚二乙酸酯为酰基供体时,反应24h,转化率为>99%,ee_P,为95.8%；以3,5-二甲基苯酚乙酸酯为酰基供体时,反应8h,转化率>99%,ee_P达91.5%。
进一步对反应底物的范围进行了拓展,均取得不错的结果,发现带有给电子基团的结构优于带有吸电子基团,邻位带有取代基的反应速度稍慢。以3,5-二甲基苯乙醇的DKR为例(底物浓度100mmol/L),该DKR的最适酰基供体为4-氯苯酚乙酸酯,以CD550为消旋催化剂时,反应24h,底物转化完全,产物ee值为97.4%；以CD8604为消旋催化剂时,反应3h,底物转化完全,产物ee值为96.5%。
鉴于树脂优异的消旋化催化性能,进一步制备了具有类似功能基团的固体超强酸Fe_2O_3/SO_4~(2-)催化剂,该催化剂具备良好的催化消旋能力,同时完全不溶于有机溶剂,可以耦合脂肪酶催化仲醇的DKR反应。
成功构建了固体超强酸Fe_2O_3/SO_4~(2-)耦合脂肪酶催化1-苯乙醇的DKR反应体系。当采用乙酸4-氯乙酸苯酯为酰基供体参与反应时(底物浓度100mmol/L),反应3h,底物转化率>99%,产物ee值为95.4%；采用乙酸3,5-二甲基苯酯为酰基供体参与反应时,反应12h,转化率达到90.5%,产物ee值为95.1%。
以固体超强酸Fe_2O_3/SO_4~(2-)作为消旋催化剂的DKR反应体系具有一定的适用范围,应用于多种芳香仲醇均取得不错的结果。以3,5-二甲基苯乙醇的DKR为例(底物浓度100mmol/L),该DKR的最适酰基供体仍为4-氯苯酚乙酸酯,反应3h,底物转化率>99%,产物ee值为93.7%。
利用酶促选择性醇解反应拆分消旋(RS)-炔丙醇酮乙酸酯制备获得高光学纯度的(R)-炔丙醇酮和(S)-炔丙醇酮乙酸酯,奠定了(RS)-炔丙醇酮的动态动力学拆分的酶学基础,同时对产物(R)-炔丙醇酮的消旋进行了研究。
In this paper, two kinds of acid catalysts were chosen as racemization catalysts and the catalytic performance were investigated. And the two kinds of acid catalysts could be applied to the DKR of several secondary aromatic alcohols successfully. The main conclusions were as follows:
Two acid resins with highly efficient racemization activity were screened and showed great potential to apply to the DKR of secondary aromatic alcohols. They could racemize (S)-1-phenylethanol almost completely in 6.5h at 40℃.
A series of phenyl acetate derivatives were synthesized and investigated for increasing the eep. And the selectivity of the DKR of 1-phenylethanol really could be successfully enhanced by using more complex acyl donors to inhibit the acid resin-catalyzed transesterification. When 1,3-Diacetoxybenzene and CD 8604 was used as acyl donor and racemization catalyst respectively, good yield (>99%) and high ee value of product (95.8%) were obtained. Good results were also obtained when 1,2-Diacetoxybenzene and 3,5-dimethyl phenyl acetate as acyl donors.
To expand the application area of the results, several substrates with different substitution groups on its benzene ring were tested and most DKR of them were performed successfully. For 1-(3,5-dimethylphenyl)ethanol, when 4-chlorophenyl acetate and CD 550 was used as acyl donor and racemization catalyst respectively, the product with 97.4%ee could be obtained in nearly 99% yield. When CD8604was used as racemization catalyst, the ee value of product was 96.5% with nearly the same yield as CD550.
Solid superacid Fe2O3/SO42- was prepared as racemization catalyst with excellent racemization capacity and also showed great potential to apply to DKR of several secondary aromatic alcohols.
The DKR of 1-phenylethanol catalyzed by lipase Novozym435-solid superacid Fe2O3/SO42- combo was established successfully, when 4-chlorophenyl acetate as acyl donor, good yield (>99%) and high ee value of product (95.4%) were obtained after 3h's reaction. While 3,5-dimethyl phenyl acetate as acyl donor, the yield and ee value of product was 90.5% and 95.1% respectively after 12h's reaction.
The Novozym435-solid superacid Fe2OSO42- combo catalyzed DKR system was also suitable for several secondary aromatic alcohols. For different substrates, appropriate acyl donor that gave good result was different. For DKR of 1-(3,5-dimethylphenyl)ethanol, the appropriate acyl donor was still 4-chlorophenyl acetate. After 3h's reaction, the yield and ee value of product was>99% and 93.7% respectively.
(RS)-4-hydroxy-3-methyl-2-(2'-propynyl)-2-cyclopentenone acetate was successfully resoluted by lipase-catalyzed alcoholysis through adjusting the basicity of organic reaction system, and the product was obtained in both high conversion and ee value. This information made good preparation for the DKR of (RS)-4-hydroxy-3-methyl-2-(2'-propynyl)-2-cyclopentenone.
引文
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