CN114540844A - 一种电催化下苯并噻吩衍生物的制备方法 - Google Patents
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Abstract
本发明公开了属于有机合成技术领域的一种电催化下苯并噻吩衍生物的制备方法。所述方法为:向反应器中,加入摩尔比为1:3的烷基苯基乙炔类物质与取代苯磺酰肼,加入四丁基六氟磷酸铵,加入体积比为47:3的六氟异丙醇与硝基甲烷作为溶剂,通过电催化策略促进反应进行。待反应完毕后,使用旋转蒸发仪浓缩得到粗产物,再经过硅胶柱层析分离得到目标产物。本发明提供的苯并噻吩衍生物的合成方法具有科学合理,合成途径绿色环保,无需金属催化剂;反应条件温和,反应温度为室温;底物在弱电流下即可反应;合成方法简单,反应快速;目标化合物收率较高,产品易于纯化等特点。其反应方程式如下:
Description
技术领域
本发明属于有机合成技术领域,具体涉及一种电催化下苯并噻吩衍生物的制备方法。
背景技术
苯并噻吩类化合物在自然界中广泛存在,其衍生物具有多种生物活性、药用价值以及材料应用:如预防骨质疏松症、改善细胞渗透性、电致发光材料、心血管保护、预防乳腺癌、选择性雌激素调节等多方面应用。((a)Tetrahedron.2013,69,7082-7089.(b)J.Med.Chem.2007,50,5644–5654.(c)Org.Chem.Front.2016,3,1126-1130.)
Indian Institute of Technology Madras大学的Perumal Saravanan andPazhamalai Anbarasan报道了合成苯并噻吩衍生物的方法:在钯催化下二溴取代烯基的邻位苯硫酚类物质分子内环化合成苯并噻吩衍生物。(Org.Lett.2014,16,848-851.)反应式见式Ⅰ:
上述方法具有使用金属催化剂以及反应温度高、额外使用磷催化剂等明显的缺陷。
发明内容
为了克服上述合成苯并噻吩衍生物现有技术的缺陷,本发明提供了一种在电催化促进下制备苯并噻吩衍生物的方法。
电催化合成反应具有很多显著的优势:可以避免使用有毒或难以处理的催化剂,电子是绿色的反应试剂,反应产物纯度高容易分离,对环境几乎无污染;在电催化反应中,可通过改变电极电压或电流来调控反应速率以避免副反应的发生,从而提高目标产品的选择性以及收率。
一种电催化策略下苯并噻吩衍生物的制备方法,所述苯并噻吩衍生物具有式Ⅱ所示的结构:
R1取代基团选自甲基、异丙基、环丙基、叔丁基、戊基且R2选自甲基;或者R1选自甲基且R2取代基团选自丙基、环己基、叔丁基、甲氧基。其特征在于,向反应器中,加入摩尔比为1:3的烷基苯基乙炔类物质与取代苯磺酰肼类化合物,加入四乙基六氟磷酸铵作为电解质,加入体积比为47:3的六氟异丙醇与硝基甲烷作为溶剂,通过电催化策略促进反应进行。待反应完毕后,使用旋转蒸发仪浓缩得到粗产物,再经过硅胶柱层析分离得到目标产物。其化学过程见反应式Ⅲ:
所述的烷基苯基乙炔、取代苯磺酰肼的摩尔比值为1:3,所述电解质为四乙基六氟磷酸铵,所述溶剂为六氟异丙醇与硝基甲烷的体积比值为47:3,通过电催化策略促进反应进行,所用电极材料为石墨毡,所用电流为5mA,反应温度为室温,反应时间为8h。
本发明的有益效果为:本发明提供的苯并噻吩衍生物合成方法科学合理,提供了一种合成苯并噻吩衍生物新途径,通过本方法得到了具有多种取代基的苯并噻吩衍生物,其特点为:合成途径绿色环保,无需金属催化剂;反应温度为室温,代替了高温反应条件;底物在弱电流下即可反应;合成方法简单;目标化合物收率较高,产品易于纯化。
附图说明
图1为实施例2制备的化合物3ba的NMR图谱;
图2为实施例5制备的化合物3ea的NMR图谱;
图3为实施例9制备的化合物3ae的NMR图谱。
具体实施方式
下面结合附图和具体的实施例对本发明进一步详细的说明:
下述实施例中所述试验方法,如无特殊说明,均为常规方法;所述试剂和材料,如无特殊说明,均可从商业途径获得。
实施例1
苯并噻吩衍生物3aa的制备
向10mL无隔膜电解槽加入1-苯基-1-丙炔1a(0.2mmol,23.2mg)、对甲苯磺酰肼2a(0.6mmol,111.7mg)、四乙基六氟磷酸铵(0.2mmol,55.0mg),阴、阳电极均采用石墨毡电极(1cm x 1cm x 0.5cm)。后向体系充换氮气,加入六氟异丙醇(4.7mL)和硝基甲烷(0.3mL)。于室温、5mA恒定电流下进行电解,反应8h。反应完毕后,使用旋转蒸发仪除去溶剂得到粗产物,粗产物经柱层析分离(200-300目硅胶,石油醚/乙酸乙酯=20/1),使用旋转蒸发仪除去溶剂,得到目标产物苯并噻吩衍生物3aa,其收率为75%。
谱图解析数据3aa:
1H NMR(CDCl3,500MHz):δ7.61(s,1H),7.56–7.45(m,3H),7.39–7.32(m,2H),7.31–7.23(m,1H),7.08(d,J=7.8Hz,1H),2.44(s,3H),2.13(s,3H);13C NMR(CDCl3,125MHz):δ140.09,137.92,136.35,134.42,133.85,130.94,130.62,129.38,129.01,128.65,123.21,122.11,21.31,7.47.
实施例2
用1b代替实例1中的1a,其他条件同实例1,实验结果见表1。
谱图解析数据3ba:
1H NMR(500MHz,CDCl3):δ7.55(s,1H),7.54–7.45(m,3H),7.34–7.29(m,2H),7.23(d,J=7.8Hz,1H),6.86(d,J=7.7Hz,1H),3.05(p,J=7.1Hz,1H),2.42(s,3H),1.37(d,J=7.0Hz,6H);13C NMR(125MHz,CDCl3)δ143.11,140.24,137.74,136.68,133.71,131.51,131.02,129.10,128.97,128.43,123.28,121.41,27.24,21.37,21.31.
实施例3
用1c代替实例1中的1a,其他条件同实例1,实验结果见表1。
谱图解析数据3ca:
1H NMR(500MHz CDCl3):δ7.54(s,1H),7.53–7.50(m,2H),7.50–7.47(m,1H),7.46–7.42(m,2H),7.25(d,J=7.1Hz,1H),7.03(d,J=7.8Hz,1H),2.42(s,3H),1.75(tt,J=8.6,5.4Hz,1H),1.22(dt,J=6.8,4.9Hz,2H),0.93–0.86(m,2H);13C NMR(125MHz,CDCl3):δ140.02,138.62,138.29,136.34,133.77,131.10,130.46,129.19,128.92,128.84,21.29,6.86,6.57.
实施例4
用1d代替实例1中的1a,其他条件同实例1,实验结果见表1。
谱图解析数据3da:
1H NMR(500MHz,CDCl3):δ7.52(s,1H),7.51–7.41(m,3H),7.25(dd,J=7.8,1.7Hz,2H),7.21–7.11(m,1H),6.53(d,J=7.8Hz,1H),2.40(s,3H),1.31(s,9H);13C NMR(125MHz,CDCl3):δ145.78,140.26,138.21,135.63,133.78,133.27,132.19,128.72,128.59,128.49,123.27,120.91,35.23,30.60,21.30.
实施例5
用1e代替实例1中的1a,其他条件同实例1,实验结果见表1。
谱图解析数据3ea:
1H NMR(CDCl3,500MHz):δ7.59(s,1H),7.51(dddd,J=11.7,6.9,4.6,2.4Hz,3H),7.36–7.31(m,2H),7.29–7.23(m,1H),6.99(d,J=7.8Hz,1H),2.71–2.49(m,2H),2.43(s,3H),1.72(p,J=7.5Hz,2H),1.27(tt,J=8.7,4.8Hz,5H),0.84(t,J=6.9Hz,3H);13C NMR(CDCl3,125MHz):δ140.17,138.69,138.40,136.46,133.77,131.03,130.98,129.24,129.00,128.46,123.26,121.85,31.63,27.71,23.63,22.08,21.30,13.85.
实施例6
用2b代替实例1中的2a,其他条件同实例1,实验结果见表1。
谱图解析数据3ab:
1H NMR(CDCl3,500MHz):δ7.62(s,1H),7.51(ddd,J=13.6,7.9,6.1Hz,3H),7.38–7.32(m,2H),7.28(dd,J=7.8,1.6Hz,1H),7.10(d,J=7.8Hz,1H),2.67(t,J=7.6Hz,2H),2.14(s,3H),1.68(dt,J=15.0,7.5Hz,2H),0.95(t,J=7.3Hz,3H);13C NMR(CDCl3,125MHz):δ144.89,137.96,136.33,134.48,133.39,131.17,130.64,129.38,129.02,128.66,123.22,121.49,37.66,24.20,13.65,7.48.
实施例7
用2c代替实例1中的2a,其他条件同实例1,实验结果见表1。
谱图解析数据2ac:
1H NMR(CDCl3,500MHz):δ7.67(s,1H),7.57–7.45(m,3H),7.39–7.33(m,2H),7.31(dd,J=7.9,1.7Hz,1H),7.10(d,J=7.9Hz,1H),2.59(td,J=11.4,9.7,5.5Hz,1H),2.13(s,3H),1.96–1.81(m,5H),1.48–1.35(m,5H),1.26(d,J=5.8Hz,2H);13C NMR(CDCl3,125MHz):δ149.55,137.25,135.65,133.87,131.24,130.53,130.00,128.65,128.31,127.95,122.60,119.26,43.71,33.49,25.93,25.20,6.77.
实施例8
用2d代替实例1中的2a,其他条件同实例1,实验结果见表1。
谱图解析数据3ad:
1H NMR(500MHz,CDCl3):δ7.85(s,1H),7.57–7.46(m,4H),7.40–7.33(m,2H),7.14(d,J=7.9Hz,1H),2.15(s,3H),1.35(s,9H);13C NMR(125MHz,CDCl3):δ153.52,137.81,136.22,134.75,130.87,130.65,130.36,129.38,129.01,128.64,123.09,118.66,35.28,31.14,7.50.
实施例9
用2e代替实例1中的2a,其他条件同实例1,实验结果见表1。
谱图解析数据3ae:
1H NMR(CDCl3,500MHz):δ7.57–7.46(m,3H),7.37–7.34(m,3H),7.11(d,J=8.4Hz,1H),6.97(dd,J=8.4,2.5Hz,1H),3.88(s,3H),2.12(s,3H);13C NMR(CDCl3,125MHz):δ160.97,137.99,137.83,133.46,130.68,129.39,129.02,128.63,125.77,124.46,118.78,107.34,55.99,7.51.
表1
Claims (2)
2.按照权利要求1所述的制备方法,其特征在于:所述的烷基苯基乙炔、取代苯磺酰肼的摩尔比值为1:3,所述电解质为四乙基六氟磷酸铵,所述溶剂为六氟异丙醇与硝基甲烷的体积比值为47:3,通过电催化策略促进反应进行,所用电流为5mA,所用电极材料为石墨毡,反应温度为室温,反应时间为8h。
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