29171-20-8

基本信息
3,7-二甲基-6-辛烯-1-炔基-3-醇
2-Dehydrolinalool
(+/-)-Dehydrolinalool
DEHYDRO-BETA-LINALOOL
3,7-dimethyl-6-octen-1-yn-3-o
3,7-dimethyloct-6-en-1-yn-3-o
3,7-dimethyl-6-octen-1-yn-3-ol
6-Octen-1-yn-3-ol, 3,7-dimethyl-
(+/-)-3,7-Dimethyl-6-octen-1-yn-3-ol
物理化學(xué)性質(zhì)
安全數(shù)據(jù)
制備方法

110-93-0

4301-14-8

29171-20-8
在-78℃條件下,向6-甲基庚-5-烯-2-酮(5.05g,40mmol)的四氫呋喃(THF,100mL)溶液中緩慢滴加0.5M乙炔基溴化鎂的THF溶液(96mL,48.0mmol),使用恒壓滴液漏斗控制滴加速度。反應(yīng)混合物逐漸形成白色漿狀物,隨后緩慢升溫至室溫并持續(xù)攪拌2小時(shí)。反應(yīng)完成后,用飽和氯化銨(NH4Cl)水溶液淬滅反應(yīng),隨后用乙醚進(jìn)行萃取。分離有機(jī)層,用飽和食鹽水洗滌,無(wú)水硫酸鈉(Na2SO4)干燥,過(guò)濾后減壓濃縮。通過(guò)快速柱層析(FCC,洗脫劑梯度:0%至35%乙酸乙酯/己烷)純化殘余油狀物,得到目標(biāo)產(chǎn)物3,7-二甲基辛-6-烯-1-炔-3-醇(CapW-24步驟A,5.87g),為無(wú)色油狀物。核磁共振氫譜(500MHz,CDCl3)δ5.28-5.12(m,1H),2.48(s,1H),2.39-2.26(m,1H),2.24-2.15(m,1H),2.09(br.s.,1H),1.79-1.65(m,8H),1.56-1.50(m,3H)。
參考文獻(xiàn):
[1] Journal of the American Chemical Society, 2002, vol. 124, # 18, p. 5025 - 5036
[2] Tetrahedron Letters, 1999, vol. 40, # 46, p. 8113 - 8114
[3] Chemistry - A European Journal, 2006, vol. 12, # 11, p. 3006 - 3019
[4] Chemical Communications, 2015, vol. 51, # 5, p. 892 - 894
[5] Tetrahedron, 2005, vol. 61, # 20, p. 4793 - 4803