63006-93-9

基本信息
3-羥甲基-1,2,3,4-四氫異喹啉
(1,2,3,4-四氫異喹啉-3-基)甲醇
1,2,3,4-四氫異喹啉-3-甲醇 10G
(1,2,3,4-四氫-異喹啉-3-YL)-甲醇
1,2,3,4-Tetrahydro-3-isoquinolinemethano
1,2,3,4-tetrahydro-3-isoquinolineMethanol
1,2,3,4-TETRAHYDROISOQUINOLINE-3-METHANOL
3-IsoquinolineMethanol,1,2,3,4-tetrahydro-
3-HYDROXYMETHYL-1,2,3,4-TETRAHYDROISOQUINOLINE
物理化學(xué)性質(zhì)
制備方法

79815-19-3

18881-17-9
一般步驟:該合成方法參照文獻[6]進行改進。在氮氣保護下,將LiAlH4(1.98 g,52.0 mmol)懸浮于無水THF(100 mL)中,攪拌并冷卻至0℃。隨后,緩慢滴加(S)-1,2,3,4-四氫異喹啉-3-甲酸甲酯(2.50 g,13.0 mmol)的THF溶液。反應(yīng)混合物在0℃下持續(xù)攪拌3小時,反應(yīng)進程通過薄層色譜(TLC)監(jiān)測,展開劑為石油醚:乙酸乙酯(70:30,Rf = 0.43)。反應(yīng)完成后,在0℃下緩慢加入飽和硫酸鈉溶液(4 mL)和THF(20 mL)以淬滅過量的LiAlH4。過濾除去無機固體,濾餅用乙酸乙酯(3×30 mL)洗滌。合并有機相,用無水硫酸鈉干燥,減壓濃縮,得到(S)-3-羥甲基-1,2,3,4-四氫異喹啉(4),為黃色結(jié)晶固體,產(chǎn)量2.09 g(收率98%,熔點95-97℃)。產(chǎn)物的比旋光度與文獻[6]報道一致。1H NMR(400 MHz,CDCl3)δ: 2.57(dd,1H,J = 10.8, 11.2 Hz),2.70(dd,1H,J = 4.34, 16.42 Hz),3.05-3.10(m,1H),3.49(dd,1H,J = 8.17, 10.82 Hz),3.78(dd,1H,J = 3.98, 10.60 Hz),4.05(s,2H),7.01-7.15(m,4H)。13C NMR(100 MHz,CDCl3)δ: 135.6, 133.9, 129.3, 126.3, 126.0, 125.9, 65.8, 55.0, 47.83, 30.9。
參考文獻:
[1] South African Journal of Chemistry, 2010, vol. 63, p. 195 - 198
[2] European Journal of Medicinal Chemistry, 2013, vol. 66, p. 407 - 414