CN114890883A - 一种茚酮及其制备方法 - Google Patents
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
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Abstract
Description
技术领域
本发明属于有机合成技术领域,涉及一种茚酮及其制备方法。
背景技术
茚酮骨架广泛存在于天然产物、药物、农药等生物活性分子中,也是有机发光、光致变色、染料等材料中的结构单元。某些茚酮类化合物不仅自身具有较好的生物活性,而且还能作为中间体用于药物合成中。如:茚达曲林、替氟达嗪及托特罗定等。
因此建立一种快速、便捷、有效的茚酮的合成方法对科技进步有着极其重要的意义。
发明内容
本发明的目的就是提供一种茚酮及其制备方法。
本发明的目的可以通过以下技术方案来实现:
一种茚酮的制备方法,包括:将邻二卤代苯系化合物、二苯乙炔类化合物、羰基源在PdCl2的催化作用下进行反应,即得到茚酮;
其中,所述的邻二卤代苯系化合物为具有如式(I)所示结构式的化合物,
式中,R1为H或CH3;R2为H、CH3、COOCH3、CF3、F或Cl中的一种;
所述的二苯乙炔类化合物为具有如式(II)所示结构式的化合物,
式中,R3、R4分别为H、CH3、OCH3、F或Cl中的一种。
进一步地,上述反应过程包括:将邻二卤代苯系化合物、二苯乙炔类化合物、羰基源、TBAI、DBU、PdCl2于有机溶剂中混合,并在100-130℃下搅拌反应23-25h,即得到茚酮。
进一步地,所述的邻二卤代苯系化合物、二苯乙炔类化合物、羰基源、TBAI(四丁基碘化铵)、DBU(1,8-二氮杂二环十一碳-7-烯)、PdCl2的投料比为(1.8-2.2):(0.8-1.2):(0.8-1.2):(0.8-1.2):(2.8-3.2):(0.08-0.12)。
进一步地,所述的羰基源为Mo(CO)6。
进一步地,所述的有机溶剂为1,4-二氧六环。
进一步地,反应在惰性气体氛围中进行。
进一步地,所得反应产物混合液依次经过稀释、洗涤、干燥、柱层析分离后,得到茚酮。
进一步地,稀释过程中,所用稀释剂为石油醚;洗涤过程中,所用洗涤剂为饱和食盐水。
进一步地,干燥过程依次包括采用固体Na2SO4干燥,以及减压干燥。
进一步地,柱层析分离过程中,所用洗脱剂为乙酸乙酯与石油醚以体积比1:50组成的混合液。
一种茚酮,采用如上述的方法制备而成。
在本反应中,邻二卤代苯系化合物、二苯乙炔类化合物主要用作底物;羰基源为Mo(CO)6;PdCl2主要用作催化剂;TBAI主要用作添加剂稳定反应中产生的纳米钯;DBU主要用作一种优良的碱脱酸剂。
与现有技术相比,本发明提供了一种将邻二卤代苯和二苯乙炔催化合成茚酮的方法,以1,4-二氧六环为反应溶剂,在120℃下、N2氛围中即可进行反应,反应时间为23-25小时,具有耗能低、产率高等优点。
具体实施方式
下面结合具体实施例对本发明进行详细说明。
一种茚酮的制备方法,包括以下步骤:
1)在有机溶剂1,4-二氧六环中,浸入邻二卤代苯系化合物与二苯乙炔类化合物,同时加入羰基源Mo(CO)6、TBAI、DBU、催化剂PdCl2,并在惰性气体氛围中100-130℃下搅拌反应23-25h,同时用薄层色谱法监测反应,得到产物混合液;
其中,邻二卤代苯系化合物为具有如式(I)所示结构式的化合物,
式中,R1为H或CH3;R2为H、CH3、COOCH3、CF3、F或Cl中的一种;优选为结构式1-1至1-7中的一种:
二苯乙炔类化合物为具有如式(II)所示结构式的化合物,
式中,R3、R4分别为H、CH3、OCH3、F或Cl中的一种;优选为结构式2-1至2-5中的一种:
邻二卤代苯系化合物、二苯乙炔类化合物、羰基源Mo(CO)6、TBAI、DBU、PdCl2的投料比为(1.8-2.2):(0.8-1.2):(0.8-1.2):(0.8-1.2):(2.8-3.2):(0.08-0.12),优选投料比为2:1:1:1:3:0.1;
2)将产物混合液依次经过石油醚稀释、饱和食盐水洗涤有机相、Na2SO4(s)干燥有机相、减压蒸发干燥,得到初提纯产物;
3)以体积比1:50的乙酸乙酯与石油醚组成的混合液作为洗脱剂,用快速色谱法纯化初提纯产物,得到茚酮。
基于上述优选的邻二卤代苯系化合物与二苯乙炔类化合物,所得茚酮的结构式包括具有以下结构式的化合物:
本实施例以本发明技术方案为前提进行实施,给出了详细的实施方式和具体的操作过程,但本发明的保护范围不限于下述的实施例。
实施例1:
一种茚酮的制备方法,包括以下步骤:
1)室温下,在4mL1,4-二氧六环中,浸入邻二卤代苯(0.5mmol)与二苯乙炔(0.25mmol),同时加入Mo(CO)6(0.25mmol)、TBAI(0.25mmol)、DBU(0.75mmol)、PdCl2(0.025mmol),并在N2氛围中120℃下搅拌反应24h,同时用薄层色谱法监测反应,得到产物混合液;
2)将产物混合液依次经过石油醚(20mL)稀释、饱和食盐水洗涤并用柱层析分离有机相、Na2SO4(s)干燥有机相、减压蒸发干燥,得到初提纯产物;
3)以体积比1:50的乙酸乙酯与石油醚组成的混合液作为洗脱剂,用快速色谱法纯化初提纯产物,得到橙色固体,即为茚酮,产率91%(反应温度100℃时收率为58%,反应温度为130℃时收率为68%)。
产品(反应温度为120℃)表征结果如下:
1H NMR(500MHz,CDCl3)δ7.50(d,J=7.0Hz,1H),7.36–7.25(m,6H),7.23–7.12(m,6H),7.06(d,J=7.2Hz,1H).
13C NMR(126MHz,CDCl3)δ196.58,155.39,145.27,133.51,132.75,132.43,130.79,130.04,129.36,129.02,128.85,128.56,128.14,127.81,123.04,121.33.
实施例2:
一种茚酮的制备方法,包括以下步骤:
1)室温下,在4mL1,4-二氧六环中,浸入邻二卤代苯(0.5mmol)与二苯乙炔类化合物(0.25mmol),同时加入Mo(CO)6(0.25mmol)、TBAI(0.25mmol)、DBU(0.75mmol)、PdCl2(0.025mmol),并在N2氛围中120℃下搅拌反应24h,同时用薄层色谱法监测反应,得到产物混合液;
2)将产物混合液依次经过石油醚(20mL)稀释、饱和食盐水洗涤有机相、Na2SO4(s)干燥有机相、减压蒸发干燥,得到初提纯产物;
3)以体积比1:50的乙酸乙酯与石油醚组成的混合液作为洗脱剂,用快速色谱法纯化初提纯产物,得到橙色固体,即为茚酮,产率85%。
产品表征结果如下:
1H NMR(500MHz,CDCl3)δ7.61(d,J=7.1Hz,1H),7.43–7.37(m,3H),7.35–7.30(m,1H),7.29–7.23(m,2H),7.19–7.11(m,3H),7.03–6.97(m,2H).
13C NMR(126MHz,CDCl3)δ196.16,164.18,162.19,154.13,144.95,133.58,131.78,131.71,131.57,130.58,130.55,130.49,129.17,128.54,126.60,123.14,121.10,116.26,116.10,115.42,115.26.
实施例3:
一种茚酮的制备方法,包括以下步骤:
1)室温下,在4mL1,4-二氧六环中,浸入邻二卤代苯(0.5mmol)与二苯乙炔类化合物(0.25mmol),同时加入Mo(CO)6(0.25mmol)、TBAI(0.25mmol)、DBU(0.75mmol)、PdCl2(0.025mmol),并在N2氛围中120℃下搅拌反应24h,同时用薄层色谱法监测反应,得到产物混合液;
2)将产物混合液依次经过石油醚(20mL)稀释、饱和食盐水洗涤有机相、Na2SO4(s)干燥有机相、减压蒸发干燥,得到初提纯产物;
3)以体积比1:50的乙酸乙酯与石油醚组成的混合液作为洗脱剂,用快速色谱法纯化初提纯产物,得到橙色固体,即为茚酮,产率89%。
产品表征结果如下:
1H NMR(500MHz,CDCl3)δ7.61(d,J=7.1Hz,1H),7.47–7.38(m,3H),7.37–7.31(m,3H),7.30–7.26(m,2H),7.24–7.19(m,2H),7.13(d,J=7.3Hz,1H).
13C NMR(126MHz,CDCl3)δ195.77,154.31,144.69,135.56,134.08,133.66,131.57,131.21,130.91,130.53,129.85,129.36,128.92,128.55,123.28,121.18.
上述的对实施例的描述是为便于该技术领域的普通技术人员能理解和使用发明。熟悉本领域技术的人员显然可以容易地对这些实施例做出各种修改,并把在此说明的一般原理应用到其他实施例中而不必经过创造性的劳动。因此,本发明不限于上述实施例,本领域技术人员根据本发明的揭示,不脱离本发明范畴所做出的改进和修改都应该在本发明的保护范围之内。
Claims (10)
2.根据权利要求1所述的一种茚酮的制备方法,其特征在于,反应过程包括:将邻二卤代苯系化合物、二苯乙炔类化合物、羰基源、TBAI、DBU、PdCl2于有机溶剂中混合,并在100-130℃下搅拌反应23-25h,即得到茚酮。
3.根据权利要求2所述的一种茚酮的制备方法,其特征在于,所述的邻二卤代苯系化合物、二苯乙炔类化合物、羰基源、TBAI、DBU、PdCl2的投料比为(1.8-2.2):(0.8-1.2):(0.8-1.2):(0.8-1.2):(2.8-3.2):(0.08-0.12)。
4.根据权利要求2所述的一种茚酮的制备方法,其特征在于,所述的羰基源为Mo(CO)6。
5.根据权利要求2所述的一种茚酮的制备方法,其特征在于,所述的有机溶剂为1,4-二氧六环,反应在惰性气体氛围中进行。
6.根据权利要求2所述的一种茚酮的制备方法,其特征在于,所得反应产物混合液依次经过稀释、洗涤、干燥、柱层析分离后,得到茚酮。
7.根据权利要求6所述的一种茚酮的制备方法,其特征在于,稀释过程中,所用稀释剂为石油醚;洗涤过程中,所用洗涤剂为饱和食盐水。
8.根据权利要求6所述的一种茚酮的制备方法,其特征在于,干燥过程依次包括采用固体Na2SO4干燥,以及减压干燥。
9.根据权利要求6所述的一种茚酮的制备方法,其特征在于,柱层析分离过程中,所用洗脱剂为乙酸乙酯与石油醚以体积比1:50组成的混合液。
10.一种茚酮,其特征在于,其采用如权利要求1至9任一项所述的方法制备而成。
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