153559-48-9
153559-48-9 結(jié)構(gòu)式
基本信息
貝沙羅汀雜質(zhì)5
蓓薩羅丁 中間體6
4-(1-(3,5,5,8,8-五甲基-5,6,7,8-四氫萘-2-基)乙烯基)苯甲酸甲酯
bexarotene methyl ester
Methyl 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)
Methyl 4-(1-(3,5,5,8,8-pentaMethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoate
methyl 4-<1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl>benzoate
4-[1-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)ethenyl]benzoic acid methyl ester
Benzoic acid, 4-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]-, methyl ester
物理化學(xué)性質(zhì)
制備方法
1779-49-3
![4-[(5,6,7,8-四氫-3,5,5,8,8-五甲基-2-萘基)羰基]苯甲酸甲酯](/CAS/GIF/153559-45-6.gif)
153559-45-6
153559-48-9
以甲基三苯基溴化鏻和4-(3,5,5,8,8-五甲基-5,6,7,8-四氫萘-2-羰基)苯甲酸甲酯為起始原料，通過Wittig反應(yīng)合成4-(1-(3,5,5,8,8-五甲基-5,6,7,8-四氫萘-2-基)乙烯基)苯甲酸甲酯。在合成過程中，發(fā)現(xiàn)化合物35的晶體適合進(jìn)行X射線衍射分析。為了完成貝沙羅汀的合成，首先利用粗制的單甲基對苯二甲酰氯（36）對化合物35進(jìn)行Friedel-Crafts?；磻?yīng)，得到酮類化合物37。隨后，通過Wittig反應(yīng)將酮37轉(zhuǎn)化為烯烴酯38。最后，烯烴酯38在氫氧化鉀作用下進(jìn)行皂化反應(yīng)，接著用鹽酸水溶液酸化，得到目標(biāo)產(chǎn)物貝沙羅汀（39）（方案2）。
參考文獻(xiàn)：
[1] Journal of Medicinal Chemistry, 2009, vol. 52, # 19, p. 5950 - 5966
[2] Patent: WO2011/103321, 2011, A1. Location in patent: Page/Page column 19
[3] Journal of Medicinal Chemistry, 1994, vol. 37, # 18, p. 2930 - 2941
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 1995, vol. 36, # 7, p. 701 - 712
[5] Journal of Medicinal Chemistry, 1995, vol. 38, # 17, p. 3368 - 3383