17996-12-2

基本信息
N-CBZ-6-氨基-1-己醇
N-(6-羥基己基)氨基甲酸芐酯
Z-NH-(CH2)6-OH
Carbamic acid, (6-hy
6-(2-Amino)-1-hexanol
6-(Z-AMINO)-1-HEXANOL
CBZ-6-AMINO-HEXAN-1-OL
Benzyl (6-hydroxyhexyl)
6-(Cbz-amino)-1-hexanol
N-CBZ-6-AMINO-HEXAN-1-OL
N-Cbz-6-hydroxyhexylamine
物理化學(xué)性質(zhì)
制備方法

4048-33-3

501-53-1

17996-12-2
一般步驟:將6-氨基-1-己醇(5.0g,42.7mmol)溶解于四氫呋喃(50mL)和水(15mL)的混合溶劑中,于0℃下緩慢滴加氯甲酸芐酯(7.3mL,51.2mmol)。在維持反應(yīng)體系溫度為0℃的條件下,緩慢加入1N氫氧化鈉溶液(12mL)以調(diào)節(jié)反應(yīng)液pH至8-9,此過(guò)程約需30分鐘。隨后,將反應(yīng)混合物在室溫下繼續(xù)攪拌30分鐘。反應(yīng)完成后,用乙醚(30mL×3)進(jìn)行萃取,合并有機(jī)相,經(jīng)無(wú)水硫酸鈉干燥后,減壓濃縮。所得粗產(chǎn)物通過(guò)二氯甲烷與己烷的混合溶劑重結(jié)晶,得到N-Cbz-6-氨基-1-己醇,為白色結(jié)晶固體(3.85g,收率90%)。產(chǎn)物結(jié)構(gòu)經(jīng)1H NMR和13C NMR確認(rèn):1H NMR(400MHz,CDCl3):δ7.34(m,5H,Ar-H),5.07(s,2H,PhCH2),4.73(br,1H,NH),3.61(t,J=6.4Hz,2H,CH2O),3.16(dt,J=6.8,6.8Hz,2H,NCH2),1.61-1.32(m,8H,CH2);13C NMR(100MHz,CDCl3):δ156.4(C=O),136.6,128.5,128.1(Ar-C),66.6(PhCH2),62.7(CH2OH),40.9(NHCH2),32.5(CH2CH2OH),29.9(NHCH2CH2),26.3(CH2CH2CH2OH),25.3(NCH2CH2CH2)。
參考文獻(xiàn):
[1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 41, p. 9716 - 9719
[2] Canadian Journal of Chemistry, 1988, vol. 66, p. 1651 - 1655
[3] Chemistry - An Asian Journal, 2011, vol. 6, # 7, p. 1800 - 1810
[4] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 4, p. 912 - 921
[5] Organic and Biomolecular Chemistry, 2018, vol. 16, # 8, p. 1343 - 1350