233276-35-2

基本信息
順式-3-(芐氧基)環(huán)丁烷-1-醇
cis-3-(benzyloxy)cyclobutan-1-ol
(1s,3s)-3-(benzyloxy)cyclobutanol
(1s,3s)-3-(benzyloxy)cyclobutan-1-ol
Cyclobutanol, 3-(phenylmethoxy)-, cis-
物理化學(xué)性質(zhì)
制備方法

30830-27-4

233276-35-2
以3-(芐氧基)-1-環(huán)丁酮為原料合成cis-3-(芐氧基)環(huán)丁醇的一般步驟:在0℃下,向3-(芐氧基)環(huán)丁-1-酮(300 mg,1.71 mmol)的無(wú)水乙醇(5 mL)溶液中分批加入硼氫化鈉(65 mg,1.71 mmol)。反應(yīng)混合物在該溫度下持續(xù)攪拌3小時(shí)。反應(yīng)完成后,通過(guò)加入冰水淬滅反應(yīng),并用乙酸乙酯(EtOAc)進(jìn)行萃取。合并有機(jī)層,依次用水和飽和食鹽水洗滌,無(wú)水硫酸鈉干燥,減壓濃縮除去溶劑。所得粗產(chǎn)物通過(guò)硅膠柱色譜法純化,洗脫劑為10%乙酸乙酯的己烷溶液,得到cis-3-(芐氧基)環(huán)丁醇,為淺黃色油狀物(300 mg,收率99%)。產(chǎn)物經(jīng)1H NMR(400 MHz,DMSO-d6)表征:δ 1.69-1.76(m,2H),2.49-2.55(m,2H),3.49-3.72(m,2H),4.33(s,2H),4.97-5.01(m,1H),7.25-7.35(m,5H)。
參考文獻(xiàn):
[1] Patent: WO2016/9296, 2016, A1. Location in patent: Page/Page column 86-87
[2] Patent: WO2018/96159, 2018, A1. Location in patent: Paragraph 0619-0622; 0652
[3] Patent: WO2014/124430, 2014, A1. Location in patent: Page/Page column 230-231
[4] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 3, p. 643 - 652
[5] Patent: WO2017/87905, 2017, A1. Location in patent: Page/Page column 232