40353-34-2

基本信息
7-硝基-1-四氫萘酮
7-硝基-3,4-二氫-2H-1-萘酮
7-NITRO-3,4-DIHYDRO-2H-NAPHTHALEN-1-ONE
7-NITROTETRA-1-LONE
7-NITROTETRALONE
1(2H)-Naphthalenone, 3,4-dihydro-7-nitro-
3,4-dihydro-7-nitro-1(2h)-naphthalenon
3,4-Dihydro-7-nitro-1(2H)-naphthalenone
7-Nitro-3,4-dihydro-1(2H)-naphthalenone
3,4-dihydro-7-nitronaphthalen-1(2H)-one
7-Nitro-1-tetralone,97%
7-Nitrotetra-1-lone 98%
7-Nitrotetralone or 7-Nitro-3,4-dihydronaphthalen-1(2H)-one
7-Nitro-3,4-dihydronaphthalen-1(2H)-one
7-Nitrotetralin-1-one
物理化學(xué)性質(zhì)
安全數(shù)據(jù)
制備方法

529-34-0

40353-34-2
以1-四氫萘酮為原料合成7-硝基-3,4-二氫-2H-1-萘酮的一般步驟:在冰浴中將濃硫酸(60 mL)冷卻至0℃。在攪拌下加入1-四氫萘酮(8 g,54.7 mmol),然后通過(guò)滴液漏斗緩慢滴加溶解在濃硫酸(18 mL)中的硝酸鉀(6 g,59.3 mmol,1.08當(dāng)量),控制反應(yīng)溫度不超過(guò)15℃。滴加完畢后,繼續(xù)攪拌反應(yīng)混合物1小時(shí)。將反應(yīng)液倒入碎冰中淬滅反應(yīng),過(guò)濾收集沉淀,并用蒸餾水洗滌。干燥后,通過(guò)乙醇/水(1:1)混合溶劑進(jìn)行重結(jié)晶,得到淺黃色固體7-硝基-3,4-二氫-2H-1-萘酮(8.5 g,產(chǎn)率81%),熔點(diǎn)為104-106℃。產(chǎn)物經(jīng)紅外光譜(IR, film)分析顯示特征吸收峰位于1675 cm?1、1500 cm?1和1340 cm?1。核磁共振氫譜(1H NMR, 400 MHz, CDCl3)數(shù)據(jù)如下:δ 2.18-2.25(2H, m, CH2),2.75(2H, t, J = 6.8 Hz, CH2),3.10(2H, t, J = 6.1 Hz, CH2),7.45(1H, d, J = 8.4 Hz, ArH),8.30(1H, dd, J = 2.4 Hz, 8.4 Hz, ArH),8.86(1H, d, J = 2.4 Hz, ArH)。
參考文獻(xiàn):
[1] Patent: WO2004/87124, 2004, A1. Location in patent: Page/Page column 47-48
[2] European Journal of Medicinal Chemistry, 2014, vol. 71, p. 237 - 249
[3] Tetrahedron Letters, 1994, vol. 35, # 38, p. 7061 - 7064
[4] Justus Liebigs Annalen der Chemie, 1927, vol. 451, p. 53
[5] Journal of the Chemical Society. Perkin transactions 1, 1969, vol. 10, p. 1376 - 1378