环戊二烯与（甲基）丙烯酸酯进行Diels-Alder反应的立体选择性研究
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摘要
本文介绍了不对称Diels-Alder反应的三大类型。对纳米固体超强酸催化合成(甲基)丙烯酸冰片酯的反应以及(甲基)丙烯酸酯与环戊二烯进行Diels-Alder反应的立体选择性问题进行了研究。
一、在纳米固体超强酸的催化下,冰片与(甲基)丙烯酸的酯化反应能顺利进行。实验考察了反应时间、反应温度、酸醇摩尔比、催化剂的用量等因素对酯化反应的影响,由此得出酯化反应的最佳反应条件,同时对催化剂S_2O_8~(2-)/ZrO_2的重复使用和活化再生情况进行了考察。并对产物进行了沸点、IR、1H NMR、13C NMR等测试。
二、论文研究了天然右旋冰片作为手性助剂得到手性的丙烯酸酯,该酯与环戊二烯进行不对称的Diels-Alder反应后水解得到相应的酸和醇,考察了不同温度、有无催化剂等因素对Diels-Alder反应的影响。
三、论文研究了各种甲基丙烯酸酯与环戊二烯进行Diels-Alder反应的立体选择性问题。考察了不同条件下反应的产率及内外型比例问题,并初步推测了催化剂的加入对产物内外型比例发生改变的可能原因。
In this dissertation, the three kinds of asymmetric Diels-Alder reaction were introduced. The preparation of bornyl acrylate and bornyl methacrylate catalyzed by nanometer solid superacids were studied. The stereoselectivity in Diels-Alder reaction of cyclopentadiene with acrylic and methacrylic ester were also studied.
Firstly, using nanometer solid superacids as the catalyst, the esterification reaction of borneol with arylic and methacrylic acid could proceed smoothly. The effects of reaction time, reaction temperature, the molar ratio of acid to borneol, the use level of catalyst on esterification reaction were discussed, and the optical reaction conditions were obtained. We also studied the reuse and the revivification of the catalyst S_2O_8~(2-)/ZrO_2. The boiling point of the product was tested. The structure of the product was characterized by IR, 1H NMR and 13C NMR spectra.
Secondly, we researched the asymmetric Diels-Alder reaction of cyclopentadiene with chiral bornyl acrylate, which was prepared by the chiral auxiliary nature borneol. The corresponding acid or alcohol were obtained after the Diels-Alder adduct were hydrolyzed or disoxidated. The effect of reaction tempertature, catalyst or noncatalyst on Diels-alder reaction were discussed.
Thirdly, we researched the stereoselectivity of Diels-Alder reaction between the different methacrylic ester and cyclopentadiene. The yield and the endo/exo ratios of the product under different conditions were studied. We also preliminarily inferred the possible reason that the endo/exo ratios were changed on the presence of catalyst.
一、在纳米固体超强酸的催化下,冰片与(甲基)丙烯酸的酯化反应能顺利进行。实验考察了反应时间、反应温度、酸醇摩尔比、催化剂的用量等因素对酯化反应的影响,由此得出酯化反应的最佳反应条件,同时对催化剂S_2O_8~(2-)/ZrO_2的重复使用和活化再生情况进行了考察。并对产物进行了沸点、IR、1H NMR、13C NMR等测试。
二、论文研究了天然右旋冰片作为手性助剂得到手性的丙烯酸酯,该酯与环戊二烯进行不对称的Diels-Alder反应后水解得到相应的酸和醇,考察了不同温度、有无催化剂等因素对Diels-Alder反应的影响。
三、论文研究了各种甲基丙烯酸酯与环戊二烯进行Diels-Alder反应的立体选择性问题。考察了不同条件下反应的产率及内外型比例问题,并初步推测了催化剂的加入对产物内外型比例发生改变的可能原因。
In this dissertation, the three kinds of asymmetric Diels-Alder reaction were introduced. The preparation of bornyl acrylate and bornyl methacrylate catalyzed by nanometer solid superacids were studied. The stereoselectivity in Diels-Alder reaction of cyclopentadiene with acrylic and methacrylic ester were also studied.
Firstly, using nanometer solid superacids as the catalyst, the esterification reaction of borneol with arylic and methacrylic acid could proceed smoothly. The effects of reaction time, reaction temperature, the molar ratio of acid to borneol, the use level of catalyst on esterification reaction were discussed, and the optical reaction conditions were obtained. We also studied the reuse and the revivification of the catalyst S_2O_8~(2-)/ZrO_2. The boiling point of the product was tested. The structure of the product was characterized by IR, 1H NMR and 13C NMR spectra.
Secondly, we researched the asymmetric Diels-Alder reaction of cyclopentadiene with chiral bornyl acrylate, which was prepared by the chiral auxiliary nature borneol. The corresponding acid or alcohol were obtained after the Diels-Alder adduct were hydrolyzed or disoxidated. The effect of reaction tempertature, catalyst or noncatalyst on Diels-alder reaction were discussed.
Thirdly, we researched the stereoselectivity of Diels-Alder reaction between the different methacrylic ester and cyclopentadiene. The yield and the endo/exo ratios of the product under different conditions were studied. We also preliminarily inferred the possible reason that the endo/exo ratios were changed on the presence of catalyst.
引文
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