CN112898162A - 一种氢化柠檬基叔胺的合成方法 - Google Patents
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Abstract
本发明公开了一种氢化柠檬基叔胺的合成方法,合成原料包括香茅醇和四氢香叶醇,以香茅醇和四氢香叶醇的溴代产物香茅基溴和四氢香叶基溴为原料,分别与二甲胺、二乙胺、二正丙胺、吗啉在有机溶剂中于水热合成反应釜中110℃~135℃加热24~72h,经冷却、过滤、蒸馏,得到4种二氢柠檬基叔胺和4种四氢柠檬基叔胺,均为无色液体,GC纯度95%以上。本发明是进一步合成含氢化柠檬基的季铵盐类化合物的重要中间体。
Description
技术领域
本发明属于天然产物化学合成技术领域,具体涉及一种氢化柠檬基叔胺的合成方法。
背景技术
山苍子,别名山鸡椒,樟科樟属植物,其根、茎、叶和果实均可入药,其果实可通过水蒸气蒸馏得到山苍子油,主要成分为柠檬醛(两种异构体:橙花醛与香叶醛),油中柠檬醛含量占70%左右,本身可以香原料,用于配制香精。在化工方面,柠檬醛是制备β-紫罗兰酮、甲基紫罗兰酮、维生素A的原料,分别用于香料和医药行业。在我国,山苍子树主要分布于长江以南各省的低山区和丘陵地带。由于农村经济的发展,人工种植山苍子林面积越来越增加,山苍子果实和山苍子油的产量也越发增加。
为了充分利用山苍子油,扩大柠檬醛的深加工范围,提高其经济价值;结合对松节油的主要成分β-蒎烯在合成多个系列季铵盐类化合物及其在抗菌应用方面所取得的成绩与经验,本专利研究并公开了一种氢化柠檬基季铵盐合成过程中的必需中间体氢化柠檬基叔胺类化合物的合成方法。
柠檬醛(两种异构体)经催化剂控制氢化可转变成香茅醛、香茅醛再还原得香茅醇,再经溴代可合成得香茅基溴;柠檬醛经完全氢化,得到的是3,7-二甲基-1-辛醇(四氢香叶醇),经溴代可合成四氢香叶基溴。香茅基溴与四氢香叶基溴是合成氢化柠檬基叔胺类化合物的主要原料。
目前,未见有所述的4种二氢柠檬基叔胺和4种四氢柠檬基叔胺类化合物的合成方法的报道,因此,本专利探究了该8种氢化柠檬基叔胺化合物的合成方法。
发明内容
本发明提出了一种氢化柠檬基叔胺的合成方法,进一步合成含氢化柠檬基的季铵盐类化合物的重要中间体。
本发明的技术方案是这样实现的:
以柠檬醛经催化控制氢化和还原所得的香茅醇再经溴代得香茅基溴,将其分别与二甲胺、二乙胺、二正丙胺、吗啉在有机溶剂中于水热合成反应釜中加热反应,合成得到4种二氢柠檬基叔胺:
以柠檬醛经完全氢化所得的四氢香叶醇经溴代得四氢香叶基溴,将其分别与二甲胺、二乙胺、二正丙胺、吗啉在有机溶剂中于水热合成反应釜中加热反应,合成得到4种四氢柠檬基叔胺:
实施本发明的这种氢化柠檬基叔胺的合成方法,具有以下有益效果:
1)扩大柠檬醛的深加工范围,提高了经济价值;
2)进一步合成含氢化柠檬基的季铵盐类化合物的重要中间体,为生产生活提供了重要的经济价值;
3)以香茅基溴为原料合成了4种二氢柠檬基叔胺(1a~1d),以四氢香叶基溴为原料合成了4种四氢柠檬基叔胺(2a~2d),目前国内外尚无相关报道,本发明为首创。
具体实施方式
下面通过实施例详述本发明,然而本发明不限于下述的实施例。
实施例1:
氢化柠檬基叔胺类化合物(1a~1d,2a~2d)的合成通法。
在70mL水热合成反应釜中,将香茅基溴或四氢香叶基溴与仲胺(二甲胺、二乙胺、二正丙胺、吗啉),按物料比1:2.1~2.2(mol/mol)投料。加入适量无水乙醇,以不装满为准,盖好,密封,置于保温效果较好的加热器中,在110~135℃加热24h~72h。冷却至室温后,将反应釜开封,倾出内容物,用吸滤法过滤去结晶物(仲胺的氢溴酸盐),并以石油醚(60~90℃)洗涤3~5次,洗出液与油状液合并,先水泵蒸馏或旋蒸去低沸物,再油泵减压蒸出氢化柠檬基叔胺产品。
实施例2:
用香茅基溴与二甲胺反应,其它实验方法和条件同实施例1,最后减压蒸馏得香茅基二甲胺(1a,R=CH3),无色液体,b.p.106~107℃/2260Pa。
IR(Vmax,cm-1):2965,2927,2856,2778(C-H),1462(CH2),1377 (CH3),1273,1064,1042(C-N);NMR,δH(CDCl3):5.095(1H,t,J=6.8Hz,6-CH),2.260(2H,t,J=7.6Hz,1-CH2),2.212(6H,s,2 α-CH3),1.978(2H,m,5-CH2),1.676(3H,s,8-CH3),1.598(3H, s,10-CH3) ,1.465(2H, m,2-CH2) ,1.298(2H, m,4-CH2) ,1.173(1H, m,3-CH ) ,0.891(3H, d,J=6.4Hz,9-CH3);δC(CDCl3):130.91(C-7),124.79(C-6),57.78(C-1),45.47(2 C-α),37.22(C-5),34.70(C-2),30.83(C-8),25.64(C-3),25.42(C-4),19.59(C-9),17.54(C-10);MS,C12H25N,m/s(%RT):183 (M+,9.47),184(M++1,1.38),58(Me2N-CH27+,100)。
实施例3:
用香茅基溴和二乙胺反应,其它实验方法和条件同实施例1,最后减压蒸馏得香茅基二乙胺(1b,R=CH2CH3),无色液体,b.p.118-120℃/1800Pa。
IR(Vmax,cm-1):2967,2927,2872,2799(C-H),1456(CH2),1376 (CH3),1293,1064,1070(C-N);NMR,δH(CDCl3):5.097(1H,t,J=6.8Hz,6-CH),2.512(4H,8,J=6.8Hz,2 α-CH2),2.415(2H,m,1-CH2),1.979(2H,m,5-CH2),1.678(3H,s,8-CH3),1.599(3H, s,10-CH3) ,1.451(2H, m,2-CH2) ,1.283(2H, m,4-CH2) ,1.162(1H, m,3-CH ) ,1.020(6H, t,J=7.2Hz,2 β-CH3) ,0.892(3H, d ,J=6.4Hz,9-CH3);δC(CDCl3):130.89(C-7),124.85(C-6),50.76(C-1),46.84(2 C-α),37.24(C-5),33.81(C-2),31.31(C-8),25.64(C-3),25.45(C-4),19.69(C-9),17.53(C-10),11.63(2 C-β);MS,C14H29N,m/s(% RT):211 (M+,13.8),212(M++1,2.4),86[(C2H5)2N-CH27+,100]。
实施例4:
用香茅基溴与二正丙胺反应,其它合成方法与条件同实施例1,最后减压蒸馏得香茅基二正丙基胺(1c,R=CH2CH2CH3),无色液体,b.p.118~120℃/860Pa。
IR(Vmax,cm-1):2959,2931,2873,2799(C-H),1458(CH2),1377 (CH3),1297,1077(C-N);NMR,δH(CDCl3):5.094(1H,t,J=6.8Hz,6-CH),2.424(2H,m,1-CH2),2.354(4H,t,1-CH2 ,J=6.8Hz,2 α-CH2),1.937(2H,m,5-CH2),1.675(3H,s,8-CH3),1.597(3H, s,10-CH3),1.446(6H,m,2 β-CH2,2-CH2) ,1.371~1.148(3H,m,4-CH2,3-CH),0.871(9H,t,J=6.4Hz,2γ-CH3,9-CH3);δC(CDCl3):130.83(C-7),124.91(C-6),56.46(2 C-α),52.07(C-1),37.25(C-5),33.99(C-2),30.89(C-8),25.65(C-3),25.49(C-4),20.25(2C-β),19.69(C-9),17.53(C-10),11.95(2 C-γ);MS,C16H33N,m/s(% RT):239 (M+,12.14),240(M++1,2.32),114[(CH3CH2CH2)2N-CH27+,100]。
实施例5:
用香茅基溴与吗啉反应,其它合成方法与条件同实施例1,最后减压蒸馏得N-香茅基吗啉(1d,R=CH2CH2OCH2CH2),无色液体,b.p.140-142℃/1330Pa。
IR(Vmax,cm-1):2959,2923,2873,2807 (C-H),1457(CH2),1376 (CH3),1261,1070 (C-N);NMR,δH(CDCl3):5.084(1H,t,J=6.8Hz,6-CH),3.693(4H,t,J=4.4Hz,2β-CH2),2.416(4H,s, 2 α-CH2), 2.328(2H,m,1-CH2),1.970(2H,m,5-CH2),1.671(3H,s,8-CH3) ,1.592(3H,s,10-CH3) ,1.488(2H,m,2-CH2),1.318(2H,m,4-CH2),1.176(1H,m,3-CH),0.894(3H,d,J=6.4Hz, 9-CH3);δC(CDCl3):130.77(C-7),124.68(C-6),66.83(2C-β),57.06(C-1),53.80(2 C-α), 37.09(C-5),33.43(C-2),30.81(C-8),25.58(C-3),25.34(C-4), 19.59(C-9),17.49(C-10);MS,C14H27NO,m/s(% RT):225 (M+,16.7),226(M++1,2.89),100[O(CH2CH2)2N-CH27+,100]。
实施例6:
用四氢香叶基溴与二甲胺反应,其它实验方法和条件同实施例1,最后减压蒸馏得四氢香叶基二甲胺(2a,R=CH3),无色液体,b.p. 90-92℃/6650Pa。
IR(Vmax,cm-1):2954,2927,2869,2780(C-H),1465(CH2),1384,1367(CH3),1272,1163,1042(C-N);NMR,δH(CDCl3):2.26(2H,t,J=4Hz,1-CH2),2.22(6H,s,2α-CH3),1.50(3H,m,2-CH2,3-CH),1.25(4H,m,4-CH,5-CH2,7-CH),1.14(3H,m,4-CH,6-CH2),0.87,0.85(9H,s,s,8-CH3,10-CH3,9-CH3);δC(CDCl3):57.96(C-1),45.63(2 C-α),39.36(C-2),37.51(C-6),34.98(C-4),31.29(C-3),28.02(C-7),24.77(C-5),22.77,22.67(C-8, C-10),19.83(C-9);MS,C12H27N,m/s(% RT): 185(M+,20.7),186(M++1,3.1),58[ (CH3)2N-CH27+,100]。
实施例7:
用四氢香叶基溴与二乙胺反应,其它实验方法和条件同实施例1,最后减压蒸馏得四氢香叶基二乙胺(2b,R=CH2CH3),无色液体,b.p.103~105℃/2100Pa。
IR(Vmax,cm-1):2956,2927,2870,2796(C-H),1468(CH2),1384,1367(CH3),1293,1178,1070(C-N);NMR,δH(CDCl3):2.53(4H,8,J=4Hz,2 α-CH2),2.42(2H,m,1-CH2),1.56~1.31(4H,m,2-CH2,3-CH, 7-CH),1.27(4H,m,5-CH2,4-CH2),1.16(2H,m,6-CH2),1.04(6H,t, J=6Hz 2 β-CH3),0.89 (6H,d, J=6Hz , 8-CH3, 10-CH3),0.87(3H,d, J=6Hz , 9-CH3);δC(CDCl3):50.91(C-1),48.93(2 C-α),39.40(C-2),37.55(C-6),33.96(C-4),31.59(C-3),28.06(C-7),24.80(C-5),22.79,22.70(C-8, C-10),19.94(C-9),11.71(2 C-β) ;MS,C14H31N,m/s(% RT): 213(M+,13.43),214(M++1,2.25) ,86[ (C2H5)2N-CH27+,100]。
实施例8:
用四氢香叶基溴与二正丙胺反应,其它实验方法和条件同实施例1,最后减压蒸馏得四氢香叶基二正丙胺(2c,R=CH2CH2CH3),无色液体,b.p.122~124℃/2100Pa。
IR(Vmax,cm-1):2958,2932,2874,2800(C-H),1464(CH2),1378,1364 (CH3),1190,1075(C-N);NMR,δH(CDCl3):2.296(4H,t,J=7.2Hz,2 α-CH2),2.145(2H,m,1-CH2),1.459~1.165(17H,m, 3-CH, 7-CH,2-CH2, 6-CH2, 4-CH2, 5-CH2, 2 β-CH2, 9-CH3),0.909~0.824(12H,m,8-CH3,10-CH3, 2 γ-CH3) ;δC(CDCl3):59.06(C-1),56.91(2 C-α),37.53(C-3, C-7) ,31.31(C-2),28.95(C-6),24.45(C-4),23.23(C-5),20.35(2C-β),14.13(C-8, C-10),11.95(2C-γ),10.73(C-9) ;MS,C16H35N,m/s(% RT): 241(M+,5.8),114[ (C3H7)2N-CH27+,100]。
实施例9:
用四氢香叶基溴与吗啉反应,其它实验方法和条件同实施例1,最后减压蒸馏得N-四氢香叶基吗啉(2d,R= CH2CH2OCH2CH2),无色液体,b.p.114-1146℃/1330Pa。
IR(Vmax,cm-1):2958,2931,2857,2807(C-H),1457(CH2),1379,1359CH3)2,1273,1120,1071(C-N);NMR,δH(CDCl3):3.685(4H,t,J=4.4Hz,2 β-CH2),2.370(4H,s,2 α-CH2),2.127(2H,t,J=6.8Hz,1-CH2),1.543~1.186(13H,m,3-CH,7-CH,2-CH2,6-CH2,4-CH2,5-CH2,9-CH3),0.901~0.834(6H,m,8-CH3,10-CH3);δC(CDCl3):67.05(2C-β),63.39(C-1),54.20(2 C-α),35.73(C-3, C-7),31.33(C-2), 28.88(C-6),24.50(C-4),23.09(C-5),14.09(C-8, C-9),10.66(C-9); MS,C14H29NO,m/s(% RT):227 (M+,12.1), 100[O(CH2CH2)2N-CH27+,100]。 至此,本发明目的得以完成。
以上所述仅为本发明的较佳实施例而已,并不用以限制本发明,凡在本发明的精神和原则之内,所作的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。
Claims (5)
2.根据权利要求1所述的氢化柠檬基叔胺的合成方法,其特征在于,所述二烷基仲胺为二甲胺、二乙胺、二正丙胺、吗啉,所述香茅基溴分别与二甲胺、二乙胺、二正丙胺、吗啉反应,得到4个二氢柠檬基叔胺类化合物,所述四氢香叶基溴与二甲胺、二乙胺、二正丙胺、吗啉反应,得到4个四氢柠檬基叔胺类化合物。
3.根据权利要求1所述的氢化柠檬基叔胺的合成方法,其特征在于,所述有机溶剂为无水乙醇。
4.根据权利要求2所述的氢化柠檬基叔胺的合成方法,其特征在于,所述香茅基溴与二烷基仲胺的物料比为:1:2.1~2.2mol,所述四氢香叶基溴与二烷基仲胺的物料比为:1:2.1~2.2mol。
5.根据权利要求1所述的氢化柠檬基叔胺的合成方法,其特征在于,所述反应时间为24~72h。
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