3-亚甲基异苯并呋喃-1(3H)-酮及其衍生物的合成研究
收稿日期: 2012-06-30
修回日期: 2012-08-30
网络出版日期: 2012-08-31
Synthesis of 3-Methyleneisobenzofuran-1(3H)-one and Their Derivatives
Received date: 2012-06-30
Revised date: 2012-08-30
Online published: 2012-08-31
以2-乙烯基苯甲酸甲酯及其衍生物为原料, 经过酯水解反应, 随后发生环氧化、环合反应制备了3-羟甲基异苯并呋喃-1(3H)-酮及其衍生物; 再和三溴化磷或者对甲苯磺酰氯发生亲核取代, 最后通过消除反应合成了3-亚甲基异苯并呋喃-1(3H)-酮及其衍生物. 在亲核取代和消除反应中, 对甲苯磺酰氯法比三溴化磷法产率高. 目标产物及其中间体有10个是新化合物. 化合物结构用1H NMR, 13C NMR, MS和IR表征. 目标产物在空气中长期放置没有发生二聚.
关键词： 3-亚甲基异苯并呋喃-1(3H)-酮; 原白头翁素; 衍生物; 合成
张继振 , 吴健 , 王雅珍 , 赵德建 , 贾洪斌 . 3-亚甲基异苯并呋喃-1(3H)-酮及其衍生物的合成研究[J]. 有机化学, 2012 , 32(12) : 2344 -2349 . DOI: 10.6023/cjoc201206030
Starting from 2-vinylbenzoic acid methyl ester and derivatives, 3-hydroxymethylisobenzofuran-1(3H)-one and derivatives were prepared through hydrolysis of esters, followed by epoxidation with m-chloroperoxybenzoic acid, cyclization reaction catalyzed by p-toluenesulfonic acid; then nucleophilic substitution with phosphorus tribromide or tosyl chloride and elimination reaction, 3-methyleneisobenzofuran-1(3H)-one and their derivatives were synthesized. The yield of tosyl chloride method was higher than phosphorus tribromide method in the nucleophilic substitution and elimination reaction. Ten target products and intermediates are new compounds. Their structures were characterized by 1H NMR, 13C NMR, MS and IR techniques. The target products did not dimerize in air over a few weeks.
Key words： 3-methylereisobenzofuran-1(3H)-one; protoanemonin; derivatives; synthesis
[1] Zhu, Z.-Y.; Yang, Y.; Tao, Y.; Wu, Y.-H.; Wu, G.-Q. J. Univ. Sci. Technol. China 1987, 17, 336 (in Chinese). (朱胄远, 杨云, 陶莹, 莫东荣, 伍越环, 吴恭谦, 中国科学技术大学学报, 1987, 17, 336.)
[2] Wu, Y.-H.; Zhu, Z.-Y.; Xi, Y.; Liu, L.; Wu, G.-Q.; Zhang, C. J. Univ. Sci. Technol. China 1991, 21, 163 (in Chinese). (伍越环, 朱胄远, 席英, 刘雷, 吴恭谦, 张超, 中国科学技术大学学报, 1991, 21, 163.)
[3] Mares, D.; Bonora, A.; Sacchetti, G.; Rubini, M.; Romagnoli, C. Cell Biol. Int. 1997, 21, 397.
[4] Sun, X.-M.; Mao, Y.-H. J. Anhui Univ. (Nat. Sci. Ed.) 1991, 1, 65 (in Chinese).(孙熊鸣, 毛羽华, 安徽大学学报(自然科学版), 1991, 1, 65.)
[5] Xi, M.-M.; Zhang, S.-Q.; Wang, X.-Y.; Fang, K.-Q.; Gu, Y. Int. J. Pharm. 2005, 298, 91.
[6] Kitamura, T.; Kawakami, Y.; Imagawa, T.; Kawanisi, M. Tetrahedron 1980, 36, 1183.
[7] Zheng, C.-G.; Wang, Z.-X.; Wu, Y.-H.; Wu, G.-Q. J. Univ. Sci. Technol. China 1999, 29, 168 (in Chinese).(郑昌戈, 王中夏, 伍越环, 吴恭谦, 中国科学技术大学学报, 1999, 29, 168.)
[8] Ferna?ndez, A. V.; Rodri?guez, C. G.; Varela, J. A.; Castedo, L.; Saa?, C. Org. Lett. 2009, 11, 5350.
[9] Kanazawa, C.; Terada, M. Tetrahedron Lett. 2007, 48, 933.
[10] Marchal, E.; Uriac, P.; Legouin, B.; Toupet, L.; van de Weghe, P. Tetrahedron 2007, 63, 9979.
[11] Kundu, N. G.; Pal, M. J. Chem. Soc., Chem. Commun. 1993, 86.
[12] Liao, H.-Y.; Cheng, C.-H. J. Org. Chem. 1995, 60, 3711.
[13] Zhou, L.; Jiang, H.-F. Tetrahedron Lett. 2007, 48, 8449.
[14] Shang, R.; Fu, Y.; Li, J.-B.; Zhang, S.-L.; Guo, Q.-X.; Liu, L. J. Am. Chem. Soc. 2009, 131, 5738.
[15] Li, J.; Chin, E.; Lui, A. S.; Chen, L.-J. Tetrahedron Lett. 2010, 51, 5937.
[16] Park, J. H.; Bhilare, S. V.; Youn, S. W. Org. Lett. 2011, 13, 2228.
[17] Rossi, R.; Carpita, A.; Bellina, F.; Stabile, P.; Mannina, L. Tetrahedron 2003, 59, 2067.
[18] Kim, B. M.; Park, J. K. Bull. Korean Chem. Soc. 1999, 20, 744.
[19] Gao, C.-S.; Zhao, L.-C.; Chen, X.-D.; Fan, X.-F.; Xie, X.-H.; Zhou, P.-Y. Macromolecules 2007, 40, 5718.
[20] Kamata, M.; Yamashita, T.; Imaeda, T.; Tanaka, T.; Masada, S.; Kamaura, M.; Kasai, S.; Hara, R.; Sasaki, S.; Takekawa, S.; Asami, A.; Kaisho, T.; Suzuki, N.; Ashina, S.; Ogino, H.; Nakano, Y.; Nagisa, Y.; Kato, K.; Kato, K.; Ishihara, Y. J. Med. Chem. 2012, 55, 2353.
[21] Liu, Z.-P.; Meng, Z.-L.; Wang, D.-F. Chin. J. Chem. 2006, 24, 504.
[22] Dale, W. J.; Starr, L.; Strobel, C. W. J. Org. Chem. 1961, 26, 2225.
[23] Ishihara, Y.; Kamata, M.; Takekawa, S.; Suzuki, N.; Kato, K. WO 2003035624, 2003 [Chem. Abstr. 2003, 38, 353842].
[24] Nishio, T. J. Chem. Soc., Perkin Trans. 1 1995, 561.
[25] Sun, H.-Y.; Que, F.-Q; Zhang, L.-F.; Ma, Q.-C.; Zhang, K.-Y.; Zhang, C.-L. Veter. Sci. China 2008, 38, 626 (in Chinese).(孙海燕, 薛飞群, 张丽芳, 马全朝, 张可煜, 张彩凌, 中国兽医科学, 2008, 38, 626.)
/
| 〈 |
|
〉 |
