醇(酚)羟基的硅烷化保护与去保护研究进展
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摘要
醇(酚)羟基的硅烷化保护是一类重要的有机合成手段,目的在于使羟基稳定化,消除或减轻其引起的副反应。保护基中硅原子连接的基团空间位阻越小,该保护基的反应活性越大,生成的相应硅醚的稳定性则越差,在弱酸或弱碱的条件下即可脱除;硅原子连接的基团越大,该保护基的反应活性则越小,硅醚化反应越难发生,需要借助催化剂才能进行。本文尽可能全面地论述了有机硅烷保护基的类型,如三甲基硅烷、三乙基硅烷、叔丁基二甲基硅烷、三异丙基硅烷、苯基取代硅烷和桥型硅烷等,并讨论了其在不同环境下的活性及稳定性。
Silylation protection of hydroxyl groups within alcohol and phenol is an important class of organic synthesis,which means to stabilize the hydroxyl groups and eliminate or mitigate the side reactions caused by them.The smaller steric hindrance of the group attached to the silicon atom in the protecting group,the greater reactivity of the protecting group,and the worse stability of the corresponding silyl ether be formed. It can be removed under weak acid or weak base conditions. The larger steric hindrance of the group attached to the silicon atom,the smaller reactivity of the protecting group,and the more difficult of silylation reaction,which requires the use of a catalyst.This article describes the types of organosilane protecting groups,such as trimethylsilane,triethylsilane,tertbutyldimethylsilane,triisopropylsilane,phenyl-substituted silane and bridging silane. The activity and stability of the protecting group under different environments are also discussed.
Silylation protection of hydroxyl groups within alcohol and phenol is an important class of organic synthesis,which means to stabilize the hydroxyl groups and eliminate or mitigate the side reactions caused by them.The smaller steric hindrance of the group attached to the silicon atom in the protecting group,the greater reactivity of the protecting group,and the worse stability of the corresponding silyl ether be formed. It can be removed under weak acid or weak base conditions. The larger steric hindrance of the group attached to the silicon atom,the smaller reactivity of the protecting group,and the more difficult of silylation reaction,which requires the use of a catalyst.This article describes the types of organosilane protecting groups,such as trimethylsilane,triethylsilane,tertbutyldimethylsilane,triisopropylsilane,phenyl-substituted silane and bridging silane. The activity and stability of the protecting group under different environments are also discussed.
引文
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[2]杨光宇.河北大学硕士学位论文,2017.
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[4]张力,张娟,马凌艳等.食品科学,2018,39(8):198~204.
[5]李涛.西南交通大学硕士学位论文,2014.
[6] M C Pirrung,Y R Lee. USP:5486633. 1996.
[7] V G Kontogianni,P Charisiadis,A Primikyri et al. Org.Biomol. Chem,2013,11(6):1013~1025.
[8] F Popp,J B Natscher,J O Daiss et al. Organometallics,2007,26(24):6014~6028.
[9]高秀秀.河南大学硕士学位论文,2017.
[10] G Aghapour, Z Abbaszadeh. Phosphorus Sulfur Silicon,2015,190(9):1464~1470.
[11] S T Kadam,S S Kim. Green Chem.,2010,41(21):94~98.
[12] D Habibi,M Nasrollahzadeh. Synth. Commun.,2010,40(21):3159~3167.
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[15] B Zeynizadeh,S Sorkhabi. Phosphorus Sulfur Silicon,2017,193(3):127~135.
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[17]李英芝,彭家建,白赢等.杭州师范大学学报(自然科学版),2015(6):561~566.
[18]菅美云,杨慧,景云荣等.合成化学,2011,19(6):689~693.
[19] M Yadegari,M Moghadam. Appl. Organomet. Chem.,2016,30(10):872~875.
[20]阮洋,彭丽亚,罗大鹏等.杭州师范大学学报(自然科学版),2013,12(4):289~296.
[21] A Ziyaei-Halimjani,M R Saidi. J. Sci.(Iran),2006,17(2):123~126.
[22] B Thirupathi, A N Prasad, R Srinivas et al. Synth.Commun.,2011,42(52):2064~2072.
[23] M Torki, S Tangestaninejad, V Mirkhani et al. Appl.Organomet. Chem.,2014,28(4):304~309.
[24] H Tajik,K Niknam,S Karimian. Iran J. Catal.,2013,3(2):107~113.
[25] H R Shaterian,M Ghashang. Phosphorus Sulfur Silicon,2007,183(1):194~204.
[26]李涛,周楠,原华等.有机硅材料,2016,30(5):380~384.
[27] M Jereb. Tetrahedron,2012,68(20):3861~3867.
[28] G Aghapour,A Kazemi Moghaddam,S Nadali. J. Chin.Chem. Soc-TAIP,2015,62(2):197~203.
[29] A Ghorbani-Choghamarani,N Cheraghi-Fathabad. Chin. J.Catal.,2010,31(9):1103~1106.
[30] D Zareyee,R Asghari,M A Khalilzadeh. Chin. J. Catal.,2011,32(11/12):1864~1868.
[31] H R Shaterian,F Khorami,A Amirzadeh et al. Phosphorus Sulfur Silicon,2008,183(10):2584~2595.
[32]龚喜,高杰,周理洁等. CN:103450118 A,2013.
[33]顾晓利,孙岚,刘国振等. CN:104448340 A,2015.
[34] M Sridhar,J Raveendra,B C Ramanaiah et al. Tetrahed.Lett.,2011,52(45):5980~5982.
[35] A Abri,S Ranjdar. J. Chin. Chem. Soc-TAIP,2014,61(8):929~934.
[36]吴松,魏金钊,童元峰等. CN:102796068A.
[37]陈丽荣,吕静,弓晓杰. CN:103724391A.
[38] E J Corey,A Venkateswarlu. J. Am. Chem. Soc.,1972,94(17):6190~6191.
[39]徐蒙蒙,胡越高,陈峰等.山东化工,2018,(4):1~2.
[40] E L Bastos,L F M L Ciscato,W J Baader. Synth. Commun.,2005,35(11):1501~1509.
[41] B S Gerstenberger,J P Konopelski. J. Org. Chem.,2005,70(4):1467~1470.
[42] M Saudi,A Van Aerschot. Molecules,2013,18(7):8524~8534.
[43] P M Reis,B Royo. Catal. Commun.,2007,8(7):1057~1059.
[44] H Liang,L Hu,E J Corey. Org. Lett.,2011,13(15):4120~4123.
[45]李琳,魏鹏飞,唐甜等.合成化学,2018,(4):300~306.
[46]李英芝.杭州师范大学硕士学位论文,2007.