227940-71-8
227940-71-8 結(jié)構(gòu)式
基本信息
7-芐基-3,7-二氮雜雙環(huán)[3.3.1]壬烷-3-羧酸叔丁酯
7-芐基-3,7-二氮雜二環(huán)[3.3.1]壬烷-3-甲酸叔丁酯
英文名稱(chēng):7-BENZYL-3-BOC-3,7-DIAZABICYCLO[3.3.1]NONANE
7-BENZYL-3-BOC-3,7-DIAZABICYCLO[3.3.1]NONANE
3-Benzyl-7-tert-butoxycarbonyl-3,7-diazabicyclo[3.3.1]nonane
tert-Butyl 7-benzyl-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate
1,1-Dimethylethyl 7-(phenylmethyl)-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate
物理化學(xué)性質(zhì)
制備方法
![TERT-BUTYL 7-BENZYL-9-OXO-3,7-DIAZABICYCLO[3.3.1]NONANE-3-CARBOXYLATE](/CAS/GIF/227940-70-7.gif)
227940-70-7
227940-71-8
以7-芐基-9-氧代-3,7-二氮雜雙環(huán)[3.3.1]壬烷-3-羧酸叔丁酯（660 mg，2 mmol）為原料，與一水合肼（0.472 mL，10 mmol）在二甘醇中混合，于60℃下攪拌。10分鐘后，加入KOH（828 mg，14.8 mmol），并將反應(yīng)混合物升溫至160℃回流8小時(shí)。反應(yīng)完成后，將混合物冷卻至室溫，用水（50 mL）稀釋?zhuān)⒂枚燃淄椋?×200 mL）萃取。合并有機(jī)層，用無(wú)水Na2SO4干燥，過(guò)濾后濃縮，得到540 mg的7-芐基-3,7-二氮雜二環(huán)[3.3.1]壬烷-3-甲酸叔丁酯，產(chǎn)率為85%。產(chǎn)物通過(guò)1H NMR、13C NMR、IR和HRMS進(jìn)行表征：1H NMR (CDCl3, 300 MHz) δ 1.52 (br s, 9H), 1.56-1.72 (br m, 2H), 1.78 (br s, 1H), 1.87 (br s, 1H), 2.12-2.26 (br m, 2H), 2.84-3.14 (br m, 4H), 3.29 (d, 1H, J = 13.5 Hz), 3.44 (d, 1H, J = 13.5 Hz), 3.99 (d, 1H, J = 13.2 Hz), 4.16 (d, 1H, J = 13.2 Hz), 7.26 (br m, 5H); 13C NMR (CDCl3, 75 MHz) δ 28.6, 28.8, 31.0, 47.4, 48.2, 58.6, 58.8, 63.3, 78.5, 126.4, 127.9, 128.4, 138.8, 154.8; IR (KBr) νmax 3428 (br), 3058, 2974, 2920, 2857, 2805, 2768, 1681, 1453, 1422, 1362, 1329, 1241, 1176, 1128 cm-1; HRMS (ESI) m/z calcd for C19H29N2O2 [M+H]+ 317.2229, found 317.2229.
參考文獻(xiàn)：
[1] Tetrahedron Letters, 2012, vol. 53, # 6, p. 623 - 626
[2] Physical Chemistry Chemical Physics, 2016, vol. 18, # 22, p. 15046 - 15053
[3] Journal of the American Chemical Society, 2008, vol. 130, # 17, p. 5654 - 5655
[4] Advanced Synthesis and Catalysis, 2008, vol. 350, # 13, p. 2001 - 2006
[5] Russian Chemical Bulletin, 2016, vol. 65, # 10, p. 2479 - 2484