CN113387914B - 一种砜基化γ-内酯的合成方法 - Google Patents

一种砜基化γ-内酯的合成方法 Download PDF

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CN113387914B
CN113387914B CN202110658797.4A CN202110658797A CN113387914B CN 113387914 B CN113387914 B CN 113387914B CN 202110658797 A CN202110658797 A CN 202110658797A CN 113387914 B CN113387914 B CN 113387914B
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饶伟浩
李琪
蒋莉莉
许盼
邓雪婉
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Xinyang Normal University
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Abstract

本发明公开了一种砜基化γ‑内酯类化合物的合成方法，属于有机合成技术领域。以2‑乙烯基芳基羧酸1为反应原料，以三价金属铱盐或二价钌盐为催化剂，以磺酰氯2以磺酰化试剂，在无机碱和可见蓝光辐射存在下有机溶剂中室温反应，得到砜基化γ‑内酯类化合物3。该发明合成方法操作方便，反应条件温和，底物官能团适用范围广泛，反应区域选择性好，收率高。

Description

一种砜基化γ-内酯的合成方法
技术领域
本发明涉及一种砜基化γ-内酯的合成方法，属于有机合成技术领域。
背景技术
砜类化合物和γ-内酯化合物具有广泛的生物活性，二者也是有机合成领域中一类重要的合成中间体，用于构筑碳碳双键、四氢呋喃类或羟基羧酸类化合物。
目前，已报道的砜基化γ-内酯的合成方法采用芳基重氮盐与三乙烯二胺-二氧化硫络合物DABCO·(SO2)2组合作为芳基砜给体，缺点是芳基重氮盐具有爆炸性，不安全环保，而且不能够用于烷基芳的引入(Org.Lett.2015,17,2482；Adv.Synth.Catal.2016,358,2707)。经过合成化学家的努力，目前发展了以稳定安全的芳基亚磺酸钠盐作为芳基砜给体(Org.Lett.2015,17,2482)，然而芳基亚磺酸钠盐仍需要由相对简单易得的磺酰氯的还原反应才能制备。采用相对简单易得磺酰氯作为合成砜基化γ-内酯的芳基砜给体不仅能够缩短合成步骤、降低反应成本，然而仅有Buchwald小组报道了以对甲苯磺酰氯作为砜基给体在常规加热条件下由铜盐催化合成砜基化γ-内酯化合物，反应需要价格昂贵的贵金属盐碳酸银(J.Am.Chem.Soc.2015,137,8069)。
基于以上方法的不足，本发明以简单易得的磺酰氯作为砜基给体通过可见光条件下的铱盐或钌盐催化2-乙烯基芳基羧酸的磺酰化/内酯化反应实现砜基化γ-内酯化合物的温和高效便捷合成。
发明内容
为了解决现有合成方法的不足，本发明提供了一种温和、操作简便、高产率及高区域选择性的砜基化γ-内酯类化合物的合成方法。以2-乙烯基芳基羧酸为反应原料，以三价金属铱盐或钌盐为光催化剂，以磺酰氯为磺酰化试剂，在无机碱存在下有机溶剂中可见蓝光辐射反应，得到砜基化γ-内酯类化合物。该发明合成方法操作方便，条件温和、工艺简单，底物官能团适用范围广泛，反应区域选择性好，收率高。
本发明所述一种砜基化γ-内酯类化合物的合成方法，包括以下步骤：在光催化剂和碱存在下，2-乙烯基芳基羧酸1与磺酰氯2在有机溶剂中可见光照射反应，得到砜基化γ-内酯类化合物3；反应方程式如下：
Figure BDA0003113018930000021
其中：R1选自氢、C1-C4烷基、苯基、取代苯基或萘基，取代苯基中取代基为卤素、C1-C4烷基、C1-C4烷氧基；R2选自氢、C1-C4烷基、C1-C4烷氧基、卤素；R3和R4各自独立选自氢、C1-C4烷基、苯基或一起组成3-6元环；R选自C1-C8烷基、苯基、取代苯基或萘基，取代苯基中取代基为卤素、C1-C4烷基、C1-C4烷氧基、三氟甲基、腈基。
进一步地，在上述技术方案中，所述碱选自碳酸铯、碳酸钠、碳酸氢钠、碳酸钾、三乙胺、DABCO、2,6-二甲基吡啶。
进一步地，在上述技术方案中，所述有机溶剂选自二氯甲烷、1,2-二氯乙烷或乙腈。
进一步地，在上述技术方案中，所述光催化剂选自Ir(ppy)3或Ru(bpy)3Cl2。
进一步地，在上述技术方案中，所述碱与2-乙烯基芳基羧酸摩尔比为1-3:1。
进一步地，在上述技术方案中，所述光催化剂与2-乙烯基芳基羧酸摩尔比为0.01-0.02:1。
进一步地，在上述技术方案中，所述磺酰氯与2-乙烯基芳基羧酸摩尔比为1-2:1。
进一步地，在上述技术方案中，反应温度为20～25℃。
进一步地，在上述技术方案中，可见光选自蓝光。
发明有益效果：
本发明的反应条件温和，反应通用性强，可以适用于各种取代基取代的底物，同时反应的区域选择性高；避免了外加氧化剂。
具体实施方式
反应条件优化实验，具体结果如下：
Figure BDA0003113018930000031
Figure BDA0003113018930000041
a以二溴甲烷为内标产物粗核磁收率；b括号内为分离收率；c以Ru(bpy)2Cl2(1mol％)代替Ir(ppy)3；d以Ru(bpy)2(PF6)2(1mol％)代替Ir(ppy)3；e以[Ir(dF)(CF3)ppy2(dtbpy)]PF6(1mol％)代替Ir(ppy)3；f无光催化剂；g避光条件下。
实施例1
Figure BDA0003113018930000042
在50mL反应瓶中，加入0.5毫摩尔2-乙烯基苯甲酸、0.005毫摩尔联吡啶铱催化剂、0.75毫摩尔对甲苯磺酰氯、1毫摩尔碳酸钠和5毫升无水二氯甲烷，在蓝光(20W/λmax＝455nm)辐射下，室温搅拌反应24小时，反应结束后处理，硅胶柱层析得到砜基化的苯并内酯化合物3a，产率为78％。白色固体，1H NMR(600MHz,CDCl3)δ7.86(d,J＝8.4Hz,2H),7.72(d,J＝7.8Hz,1H),7.67-7.64(m,1H),7.57(t,J＝7.8Hz,1H),7.39(d,J＝8.0Hz,2H),5.94(dd,J＝7.8,4.2Hz,1H),3.67(dd,J＝15.0,4.2Hz,1H),3.58(dd,J＝15.0,7.8Hz,1H),2.47(s,3H).13C NMR(150MHz,CDCl3)δ169.2,147.2,145.7,136.1,134.8,130.2,130.2,128.5,126.1,125.6,122.7,75.0,60.6,21.9.HRMS:calcd for C16H15O4S[M+H]+303.0686,found303.0686.
实施例2
按照实施例1中反应条件，仅仅改变反应底物，反应结果如下：
Figure BDA0003113018930000051
Figure BDA0003113018930000061
代表性化合物表征数据如下：
3b,白色固体，85％收率。1H NMR(600MHz,CDCl3)δ7.92-7.72(m,2H),7.53(d,J＝8.4Hz,1H),7.38(d,J＝8.4Hz,2H),7.30-7.11(m,2H),5.87(dd,J＝7.2,4.8Hz,1H),3.85(s,3H),3.63(dd,J＝15.0,4.8Hz,1H),3.55(dd,J＝15.0,7.2Hz,1H),2.46(s,3H).13C NMR(150MHz,CDCl3)δ169.2,161.4,145.6,139.4,136.2,130.2,128.4,127.1,123.6,123.5,107.9,74.8,60.7,56.0,21.8.HRMS:calcd for C17H17O5S[M+H]+333.0791,found333.0790.
3c，白色固体，82％收率。1H NMR(600MHz,CDCl3)δ7.85(d,J＝8.4Hz,2H),7.70(dd,J＝8.4,4.2Hz,1H),7.52(dd,J＝7.2,2.4Hz,1H),7.43(td,J＝8.4,2.4Hz,1H),7.40(d,J＝8.4Hz,2H),5.93(t,J＝6.6Hz,1H),3.64(dd,J＝14.4,4.8Hz,1H),3.64(dd,J＝14.4,6.6Hz,1H),2.47(s,3H).13C NMR(150MHz,CDCl3)δ167.9,164.5,162.9,145.8,142.7,136.9,130.3,128.4,127.9,127.8,124.9,124.8,122.9,122.7,112.5,112.4,74.9,60.4,21.9.19F NMR(565MHz,CDCl3)δ-109.6.HRMS:calcd for C16H14FO4S[M+H]+321.0591,found321.0589.
3d，白色固体，88％收率。1H NMR(600MHz,CDCl3)δ7.64-7.56(m,2H),7.50(t,J＝7.8Hz,1H),7.33-7.24(m,4H),3.80(d,J＝15.0Hz,1H),3.68(d,J＝15.0Hz,1H),2.65(s,3H),2.43(s,3H),1.77(s,3H).13C NMR(150MHz,CDCl3)δ168.7,151.4,145.1,140.0,137.1,134.1,131.4,130.0,128.2,123.1,119.5,81.9,63.4,27.2,21.8,17.5.HRMS:calcd forC18H19O4S[M+H]+331.0999,found 331.0997.
3e，白色固体，85％收率。1H NMR(600MHz,CDCl3)δ7.84(d,J＝7.8Hz,1H),7.62(d,J＝7.8Hz,1H),7.58(d,J＝8.4Hz,2H),7.53(t,J＝7.8Hz,1H),7.48(d,J＝7.8Hz,1H),7.27(d,J＝8.4Hz,2H),3.83(d,J＝15.0Hz,1H),3.74(d,J＝15.0Hz,1H),2.41(s,3H),1.78(s,3H).13C NMR(150MHz,CDCl3)δ168.6,150.8,145.1,137.1,134.4,123.0,129.8,128.0,125.8,125.6,122.2,83.1,62.9,27.0,21.8.HRMS:calcd for C17H17O4S[M+H]+317.0842,found 317.0840.
3f，白色固体，86％收率。1H NMR(600MHz,CDCl3)δ7.85(d,J＝7.8Hz,1H),7.63(t,J＝7.8Hz,1H),7.55(d,J＝8.4Hz,2H),7.54(t,J＝7.8Hz,1H),7.43(d,J＝7.8Hz,1H),7.27(d,J＝7.8Hz,2H),3.87(d,J＝13.8Hz,1H),3.76(d,J＝13.8Hz,1H),2.42(s,3H),2.23(dd,J＝14.4,7.2Hz,1H),2.02(dd,J＝13.8,6.6Hz,1H),0.66(t,J＝7.2Hz,3H).13C NMR(150MHz,CDCl3)δ168.9,148.8,145.1,137.2,134.3,130.0,129.8,128.0,126.9,125.7,122.4,85.7,62.1,32.7,21.8,7.1.HRMS:calcd for C18H19O4S[M+H]+331.0999,found331.0996.
3g，白色固体，88％收率。1H NMR(600MHz,CDCl3)δ7.86(dt,J＝7.8,1.2Hz,1H),7.65(td,J＝7.8,1.2Hz,1H),7.59-7.53(m,3H),7.49-7.44(m,1H),7.33-7.27(m,2H),3.85(d,J＝15.0Hz,1H),3.75(d,J＝15.0Hz,1H),2.43(s,3H),2.18(ddd,J＝14.4,12.0,4.2Hz,1H),1.96(ddd,J＝14.4,12.0,4.2Hz,1H),1.31-1.05(m,3H),0.82-0.77(m,4H).13C NMR(150MHz,CDCl3)δ169.0,149.2,145.2,137.2,134.3,130.0,129.8,128.0,126.7,125.8,122.5,85.4,62.4,39.3,24.7,22.5,21.8,13.9.HRMS:calcd for C20H23O4S[M+H]+359.1312,found 359.1310.
3h，白色固体，90％收率。1H NMR(600MHz,CDCl3)δ7.89(dd,J＝7.8,1.2Hz,1H),7.68-7.63(m,1H),7.61(d,J＝7.8Hz,1H),7.58-7.54(m,1H),7.54-7.50(m,2H),7.45-7.41(m,2H),7.35-7.31(m,2H),7.31-7.28(m,1H),7.28-7.23(m,2H),4.28(d,J＝15.0Hz,1H),4.19(d,J＝15.0Hz,1H),2.43(s,3H).13C NMR(150MHz,CDCl3)δ168.7,149.2,145.1,139.1,137.2,134.4,123.0,129.2,129.0,128.1,126.1,125.8,124.7,123.4,85.1,63.3,21.8.HRMS:calcd for C22H19O4S[M+H]+379.0999,found 379.0995.
实施例3
Figure BDA0003113018930000081
在50mL反应瓶中，加入0.5毫摩尔2-乙烯基苯甲酸、0.005毫摩尔联吡啶铱催化剂、0.75毫摩尔对甲苯磺酰氯、1毫摩尔碳酸钠和5毫升无水二氯甲烷，采用蓝光(20W/λmax＝455nm)辐射，室温搅拌反应24小时，反应结束后处理，硅胶柱层析得到砜基化的苯并内酯化合物3Aa，产率为95％。白色固体，1H NMR(600MHz,CDCl3)δ7.87(d,J＝7.5Hz,1H),7.63(dd,J＝8.3,1.0Hz,2H),7.60-7.55(m,3H),7.52(ddd,J＝8.0,6.7,1.8Hz,1H),7.47-7.38(m,4H),7.34-7.23(m,3H),4.32(d,J＝15.6Hz,1H),4.25(d,J＝15.6Hz,1H).13C NMR(150MHz,CDCl3)δ168.6,149.0,140.0,138.9,134.4,133.9,129.9,129.3,129.1,129.0,127.9,125.9,125.6,124.7,123.3,85.0,62.94.HRMS:calcd for C21H17O4S[M+H]+365.0842,found365.0842.
实施例4
按照实施例3中反应条件，仅仅改变反应底物，反应结果如下：
Figure BDA0003113018930000091
代表性化合物表征数据如下：
3Ab，白色固体，82％收率。1H NMR(600MHz,CDCl3)δ7.88(d,J＝7.8Hz,1H),7.69-7.59(m,2H),7.58-7.51(m,3H),7.47-7.38(m,2H),7.35-7.27(m,3H),6.91(d,J＝8.4Hz,8H),4.27(d,J＝15.6Hz,1H),4.19(d,J＝15.6Hz,1H),3.86(s,3H).13C NMR(150MHz,CDCl3)δ168.7,163.9,149.3,139.1,134.4,131.6,130.3,129.9,129.1,129.0,126.0,125.7,124.7,123.4,114.5,85.2,63.4,55.8.HRMS:calcd for C22H19O5S[M+H]+395.0948,found395.0946.
3Ac，白色固体，89％收率。1H NMR(600MHz,CDCl3)δ7.87(d,J＝7.2Hz,1H),7.61-7.57(m,2H),7.55-7.52(m,3H),7.45-7.43(m,4H),7.33-7.26(m,3H),4.28(d,J＝15.6Hz,1H),4.21(d,J＝15.6Hz,1H),1.33(s,9H).13C NMR(150MHz,CDCl3)δ168.6,157.9,149.0,139.1,136.9,134.3,129.9,129.1,129.0,128.0,126.3,126.0,126.0,124.8,123.5,85.1,63.2,35.3,31.1.HRMS:calcd for C25H25O4S[M+H]+421.1468,found421.1467.
3Ad，白色固体，85％收率.1H NMR(600MHz,CDCl3)δ7.95-7.84(m,1H),7.70(d,J＝8.4Hz,2H),7.67-7.54(m,7H),7.53-7.47(m,2H),7.45-7.42(m,3H),7.37-7.28(m,3H),4.33(d,J＝15.6Hz,1H),4.23(d,J＝15.6Hz,1H).13C NMR(150MHz,CDCl3)δ168.6,149.2,147.0,139.2,139.1,138.5,134.4,130.1,129.2,129.1,128.8,128.6,128.0,127.6,126.2,125.9,124.8,123.4,85.1,63.4.HRMS:calcd for C27H21O4S[M+H]+441.1155,found441.1151.
3Ae，白色固体，73％收率。1H NMR(600MHz,CDCl3)δ7.94-7.87(m,1H),7.84-7.74(m,4H),7.72-7.65(m,1H),7.63-7.52(m,2H),7.43-7.36(m,2H),7.36-7.27(m,3H),4.36(d,J＝15.6Hz,1H),4.22(d,J＝15.6Hz,1H).13C NMR(150MHz,CDCl3)δ168.4,149.4,144.1,138.5,134.8,133.1,130.3,129.3,129.3,129.0,126.3,125.4,124.6,123.1,117.8,117.2,84.7,63.4.HRMS:calcd for C22H16NO4S[M+H]+390.0795,found 390.0796.
3Af，白色固体，88％收率。1H NMR(600MHz,CDCl3)δ7.89(d,J＝7.8Hz,1H),7.72-7.66(m,2H),7.66-7.62(m,1H),7.60(d,J＝7.8Hz,1H),7.58-7.52(m,1H),7.43(dd,J＝8.4,1.2Hz,2H),7.36-7.28(m,3H),7.14(t,J＝8.4Hz,2H),4.32(d,J＝15.6Hz,1H),4.22(d,J＝15.6Hz,1H).13C NMR(150MHz,CDCl3)δ168.4,166.0(d,J＝225.5Hz,1C),149.5,139.1,136.5,134.4,131.1(d,J＝9.5Hz,2C),130.0,129.2,129.1,126.1,125.8,124.8,123.4,116.6(d,J＝22.7Hz,2C),85.0,63.6.19F NMR(565MHz,CDCl3)δ-102.7.HRMS:calcdfor C21H16FO4S[M+H]+383.0748,found 383.0743.
3Ag，白色固体，84％收率。1H NMR(600MHz,CDCl3)δ7.91(d,J＝7.8Hz,1H),7.81(d,J＝8.4Hz,2H),7.73(d,J＝8.4Hz,2H),7.66-7.61(m,1H),7.59-7.54(m,2H),7.45-7.37(m,2H),7.35-7.27(m,3H),4.35(d,J＝15.6Hz,1H),4.25(d,J＝15.6Hz,1H).13C NMR(150MHz,CDCl3)δ168.5,149.2,143.5,138.6,135.5(q,J＝33.0Hz,1C),134.6,130.2,129.3,129.2,128.8,126.5(d,J＝3.8Hz,2C),126.3,125.9,125.6,124.7,124.1,123.2(q,J＝271.4Hz,1C),123.1,122.3,120.5,84.8,63.3.19F NMR(565MHz,CDCl3)δ-63.1.HRMS:calcd forC22H16F3O4S[M+H]+433.0716,found 433.0712.
3Ah，白色固体，85％收率。1H NMR(600MHz,CDCl3)δ7.95-7.77(m,1H),7.59-7.54(m,2H),7.53-7.50(m,1H),7.49-7.46(m,1H),7.45-7.41(m,2H),7.37(d,J＝7.8Hz,1H),7.34-7.25(m,5H),4.30(d,J＝15.6Hz,1H),4.25(d,J＝15.6Hz,1H),2.33(s,3H).13C NMR(150MHz,CDCl3)δ168.6,148.9,139.7,139.4,139.0,134.6,134.2,129.8,129.1,129.0,128.9,128.3,125.8,125.0,124.7,123.4,85.0,63.0,21.2.HRMS:calcd for C22H19O4S[M+H]+379.0999,found 379.0996.
3Ai，白色固体，84％收率。1H NMR(600MHz,CDCl3)δ7.90(d,J＝7.8Hz,1H),7.68-7.61(m,1H),7.60-7.54(m,2H),7.51-7.40(m,4H),7.36-7.28(m,4H),7.28-7.23(m,1H),4.33(d,J＝15.6Hz,1H),4.22(d,J＝15.6Hz,1H).13C NMR(150MHz,CDCl3)δ168.5,162.3(d,J＝251.1Hz,1C),149.0,142.0(d,J＝6.2Hz,1C),138.7,134.5,131.3(d,J＝7.8Hz,1C),130.2,129.2,129.2,126.1,125.7,124.7,123.9(d,J＝2.6Hz,1C),123.4,121.3(d,J＝21.2Hz,1C),115.4(d,J＝24.3Hz,1C),84.9,63.3.19F NMR(565MHz,CDCl3)δ-108.8.HRMS:calcd for C21H16FO4S[M+H]+383.0748,found 383.0748.
以上实施例描述了本发明的基本原理、主要特征及优点。本行业的技术人员应该了解，本发明不受上述实施例的限制，上述实施例和说明书中描述的只是说明本发明的原理，在不脱离本发明原理的范围下，本发明还会有各种变化和改进，这些变化和改进均落入本发明保护的范围内。

Claims (5)

1.一种砜基化γ-内酯的合成方法，其特征在于，包括以下步骤：在光催化剂和碱存在下，2-乙烯基芳基羧酸1与磺酰氯2在有机溶剂中可见光照射反应，得到砜基化γ-内酯类化合物3；反应方程式如下：
Figure FDA0003919005650000011
其中：R1选自氢、C1-C4烷基、苯基、取代苯基或萘基，取代苯基中取代基为卤素、C1-C4烷基、C1-C4烷氧基；R2选自氢、C1-C4烷基、C1-C4烷氧基、卤素；R3和R4各自独立选自氢、C1-C4烷基、苯基或一起组成3-6元环；R选自C1-C8烷基、苯基、取代苯基或萘基，取代苯基中取代基为卤素、C1-C4烷基、C1-C4烷氧基、三氟甲基、腈基；所述碱选自碳酸铯、碳酸钠、碳酸氢钠、碳酸钾、三乙胺、DABCO或2,6-二甲基吡啶，有机溶剂选自二氯甲烷、1,2-二氯乙烷或乙腈；光催化剂选自Ir(ppy)3或Ru(bpy)3Cl2，可见光选自蓝光。
2.根据权利要求1所述砜基化γ-内酯的合成方法，其特征在于：所述碱与2-乙烯基芳基羧酸摩尔比为1-3:1。
3.根据权利要求1所述砜基化γ-内酯的合成方法，其特征在于：所述光催化剂与2-乙烯基芳基羧酸摩尔比为0.01-0.02:1。
4.根据权利要求1所述砜基化γ-内酯的合成方法，其特征在于：所述磺酰氯与2-乙烯基芳基羧酸摩尔比为1-2:1。
5.根据权利要求1所述砜基化γ-内酯的合成方法，其特征在于：反应温度为20～25℃。
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