171290-52-1

基本信息
3,5-雙甲氧基苯乙炔
3,5-二甲氧基苯乙炔
3,5-二甲氧基苯基乙炔
1-乙炔基-3,5-二甲氧基苯
-ETHYNYL-3 5-DIMETHOXYBENZENE 98
Benzene, 1-ethynyl-3,5-diMethoxy-
1-ETHYNYL-3 5-DIMETHOXYBENZENE 98
1-Ethynyl-3,5-diMethoxybenzene 98% (CP)
物理化學(xué)性質(zhì)
安全數(shù)據(jù)
制備方法

205746-51-6

171290-52-1
在氬氣保護(hù)下,將1-(2,2-二溴乙烯基)-3,5-二甲氧基苯(2.99 g,9.28 mmol,1當(dāng)量)溶于無(wú)水四氫呋喃(50 mL)中,于-50℃(干冰/乙腈?。┫聰嚢?。緩慢滴加正丁基鋰(24.0 mL,1.6 M的己烷溶液,38.4 mmol,4.1當(dāng)量),反應(yīng)進(jìn)程通過(guò)薄層色譜(TLC)監(jiān)測(cè)至反應(yīng)完成。反應(yīng)混合物用飽和氯化銨水溶液(40 mL)淬滅,隨后用二氯甲烷(3×20 mL)萃取。合并有機(jī)相,用無(wú)水硫酸鈉干燥,過(guò)濾后減壓濃縮,得到橙棕色油狀物(1.61 g)。通過(guò)快速柱色譜法(洗脫劑:純戊烷,隨后為19:1戊烷:乙醚)純化,得到無(wú)色結(jié)晶固體3,5-二甲氧基苯乙炔(1.22 g,收率81%),Rf = 0.24(戊烷),熔點(diǎn)205℃。其核磁共振氫譜(400.1 MHz,CDCl3)數(shù)據(jù)如下:δ 6.72(d,J = 2.3 Hz,2H,ArH),6.50(t,J = 2.3 Hz,1H,ArH),3.76(s,6H,OCH3),3.15(s,1H,C≡CH)。核磁共振碳譜(100.6 MHz,CDCl3)數(shù)據(jù)如下:δ 160.6(C),123.4(C),110.0(CH),102.3(CH),83.7(C),76.9(CH),55.4(CH3)。
參考文獻(xiàn):
[1] Tetrahedron Letters, 2009, vol. 50, # 17, p. 1969 - 1972
[2] Chemistry Letters, 2008, vol. 37, # 2, p. 174 - 175
[3] Beilstein Journal of Organic Chemistry, 2015, vol. 11, p. 273 - 279
[4] European Journal of Medicinal Chemistry, 2011, vol. 46, # 6, p. 2386 - 2396
[5] Tetrahedron, 2017, vol. 73, # 33, p. 5023 - 5028