CN112174862B - 一种苄基硫醚的合成方法 - Google Patents

一种苄基硫醚的合成方法 Download PDF

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CN112174862B
CN112174862B CN202011219594.7A CN202011219594A CN112174862B CN 112174862 B CN112174862 B CN 112174862B CN 202011219594 A CN202011219594 A CN 202011219594A CN 112174862 B CN112174862 B CN 112174862B
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曾庆乐
张巧玲
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Chengdu Univeristy of Technology
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Abstract

目前，市场上有许多用于治疗各种疾病的含硫药物，例如抗精神病药物氯丙噻吩。其中，硫醚具有广泛的生物活性。它不仅易于转化为其他类型的含硫有机化合物，而且还是许多药物合成的重要中间体。本专利公开了一种无金属催化的硫醚合成方法：在乙腈溶液中，苄基三氟甲烷磺酸季铵盐与β‑亚磺酰基酯在KOH的作用下，通过碳氮键的断裂、碳硫键的生成，以良好至优秀的收率在广泛的底物范围内合成苄基硫醚。在具有手性的季铵盐参与的反应中，以非常好的手性值保留得到了手性的硫醚。该方法具有反应条件温和，实验操作简单，无金属催化剂，产物产率高，底物适用性广，手性保留值高等优点。

Description

一种苄基硫醚的合成方法
技术领域
该专利涉及有机合成、药物合成、有机化工等研究领域，具体的方法就是β-亚磺酰基酯和苄基三氟甲烷磺酸季铵盐进行的无过渡金属催化一步合成苄基硫醚类化合物。
背景技术
目前，市场上有许多用于治疗各种疾病的含硫药物，例如抗精神病药物氯丙噻吩(Luis E.
Figure BDA0002760079330000011
Carmelo García,Virginie Lhiaubet-Vallet,Rolando Oyola1 andMiguel A.Miranda,Photochemistry and Photobiology,2009,85,895–900.)和抗菌药物头孢唑林(O.H.Jústiz,R.Fernández-Lafuente,J.M.Guisán,P.Negri,G.Pagani,M.Pregnolato,and M.Terreni,J.Org.Chem.1997,62,9099-9106)。更有趣的是硫醚具有广泛的生物活性。它不仅易于转化为其他类型的含硫有机化合物，而且还是许多药物合成的重要中间体。((a)Halama.A.J,Jirman.O,Bouskova.P,Gibala,Jarrah.K,Org.ProcessRes.Dev.2010,14,425-431.(b)O’Connor.S.E,Grosset.A,Philip.J,Fundam.Clin.Pharmacol.1999,13,145-153.(c)Tisdale.M,Kemp.S.D,Parry.N.R,Larder.B.A,Proc.Natl.Acad.Sci.U.S.A.1993,90,5653-5656.)因此，硫醚的制备受到了有机工作者的广泛关注。在过去的文献报道中合成苄基硫醚的方法很多((a)WenlongJiang,Nutao Li,Lihong Zhou,and Qingle Zeng,ACS Catal.2018,8,9899-9906.(b)Fuhai Li,Dan Wang,Hongyi Chen,Ze He,Lihong Zhou,and Qingle Zeng,Chem.Commun.,2020,56,13029-13032)，但本发明合成苄基硫醚的方法并未见报道。
我们开发了苄基三氟甲烷磺酸季铵盐与β-亚磺酰基酯在强碱的作用下一步合成苄基硫醚的合成方法，即在乙腈中，在KOH的作用下，苄基三氟甲烷磺酸季铵盐与β-亚磺酰基酯合成苄基硫醚；在使用手性的苄基三氟甲烷磺酸季铵盐时，能够得到构型翻转的目标产物，且手性值保留得非常好。
尽我们所知，未见与本申请相同的文献报道。
发明内容
本发明提供一种无金属催化苄基硫醚的合成方法。
本发明公开的苄基硫醚的合成方法均一步完成，在有机溶剂乙腈中，无过渡金属催化，仅在碱KOH的作用下β-亚磺酰基酯和苄基三甲基铵盐一步合成苄基硫醚，反应通式如下。其中R可以是芳基、杂芳基、烷基。此外，部分季铵盐苄位具有手性碳，合成的产物相应地具有手性。
Figure BDA0002760079330000021
结合下面的实施例，更详细地阐述本发明，但并不认为它们是对本发明范围的限制。
具体实施方式
实施例一
Figure BDA0002760079330000022
向装有搅拌子的25mL干净玻璃试管中加入3-(甲苯-4-亚磺酰基)-丙酸叔丁酯(1mmol)，N,N,N-三甲基苄基三氟甲烷磺酸铵(1.2mmol)和5mL乙腈，在室温下搅拌至固体完全溶解后再加入50％KOH水溶液(20mmol)。在80℃下预热的油浴中搅拌反应24小时后，通过TLC检查反应进程并确认反应完成。将反应混合物冷却至室温。然后将饱和氯化钠溶液(10mL)加入到反应混合物中淬灭，将其用乙酸乙酯(10mL)萃取三次。合并的有机层经无水MgSO4干燥，过滤，并在减压下浓缩。残余物通过硅胶快速柱色谱纯化(石油醚/乙酸乙酯用作洗脱剂)，纯化后，得到无色油状液体苄基对甲苯基硫醚产率为90％。反应方程式如下所示。
产物苄基(对甲苯基)硫醚的结构表征数据如下：
1H NMR(400MHz,CDCl3)δ7.19–7.08(m,7H),6.96(d,J＝7.9Hz,2H),3.96(s,2H),2.20(s,3H).
实施例二
用N,N,N-三甲基(2-溴苄基)三氟甲烷磺酸铵代替实施例一中的N,N,N-三甲基苄基三氟甲烷磺酸铵，得到淡黄色油状液体(2-溴苄基)对甲苯基硫醚的产率为87％。
1H NMR(400MHz,CDCl3)δ7.47(d,J＝7.7Hz,1H),7.18–7.05(m,4H),7.04–6.96(m,3H),4.08(s,2H),2.23(s,3H).
实施例三
用N,N,N-三甲基(4-叔丁基苄基)三氟甲烷磺酸铵代替实施例一中的N,N,N-三甲基苄基三氟甲烷磺酸铵，得到白色固体(4-叔丁基苄基)对甲苯基硫醚的产率为85％
1H NMR(400MHz,CDCl3)δ7.18(dt,J＝8.3,5.9Hz,6H),6.99(d,J＝8.0Hz,2H),3.99(s,2H),2.23(s,3H),1.22(s,9H).
实施例四
用N,N,N-三甲基(2-氟苄基)三氟甲烷磺酸铵代替实施例一中的N,N,N-三甲基苄基三氟甲烷磺酸铵，得到淡黄色油状液体(2-氟苄基)对甲苯基硫醚的产率为89％。
1H NMR(400MHz,CDCl3)δ7.27–7.17(m,4H),7.11–6.99(m,4H),4.10(s,2H),2.33(s,3H).
实施例五
用N,N,N-三甲基(2-溴苄基)三氟甲烷磺酸铵代替实施例一中的N,N,N-三甲基苄基三氟甲烷磺酸铵，得到淡黄色油状液体(2-溴苄基)对甲苯基硫醚的产率为89％。
1H NMR(400MHz,CDCl3)δ7.30–7.25(m,1H),7.17–6.96(m,7H),4.08(s,2H),2.23(s,3H).
实施例六
用N,N,N-三甲基(3-甲基苄基)三氟甲烷磺酸铵代替实施例一中的N,N,N-三甲基苄基三氟甲烷磺酸铵，得到无色油状液体(3-甲基苄基)对甲苯基硫醚的产率为90％。
1H NMR(400MHz,CDCl3)δ7.16–7.04(m,3H),7.04–6.92(m,5H),3.95(s,2H),2.22(s,6H).
实施例七
用N,N,N-三甲基(3-甲氧基苄基)三氟甲烷磺酸铵代替实施例一中的N,N,N-三甲基苄基三氟甲烷磺酸铵，得到淡黄色油状液体(3-甲氧基苄基)对甲苯基硫醚的产率为88％。
1H NMR(400MHz,CDCl3)δ7.17–7.07(m,3H),6.98(d,J＝7.9Hz,2H),6.72(ddd,J＝13.9,10.6,5.0Hz,3H),3.96(s,2H),3.67(s,3H),2.22(s,3H).
实施例八
用N,N,N-三甲基(4-三氟甲基苄基)三氟甲烷磺酸铵代替实施例一中的N,N,N-三甲基苄基三氟甲烷磺酸铵，得到白色固体(4-三氟甲基苄基)对甲苯基硫醚的产率为86％。
1H NMR(400MHz,CDCl3)δ7.43(d,J＝8.1Hz,2H),7.25(d,J＝8.1Hz,2H),7.18–7.07(m,2H),6.99(d,J＝8.0Hz,2H),3.99(s,2H),2.23(s,3H).
实施例九
用N,N,N-三甲基(4-氰基苄基)三氟甲烷磺酸铵代替实施例一中的N,N,N-三甲基苄基三氟甲烷磺酸铵，得到黄色固体(4-氰基苄基)对甲苯基硫醚的产率为85％。
1H NMR(400MHz,CDCl3)δ7.46(d,J＝8.3Hz,2H),7.13(dd,J＝73.0,20.1Hz,6H),3.96(s,2H),2.23(s,3H).
实施例十
用N,N,N-三甲基-1-(萘-1-基)甲基三氟甲磺酸铵代替实施例一中的N,N,N-三甲基苄基三氟甲烷磺酸铵，得到淡黄色油状液体(萘-1-基)甲基对甲苯基硫醚的产率为86％。
1H NMR(400MHz,CDCl3)δ8.06(d,J＝8.5Hz,1H),7.82–7.62(m,2H),7.52–7.36(m,2H),7.28–7.11(m,4H),6.99(d,J＝7.9Hz,2H),4.43(s,2H),2.23(s,3H).
实施例十一
用3-(甲苯-3-亚磺酰基)-丙酸叔丁酯代替实施例一中的3-(甲苯-4-亚磺酰基)-丙酸叔丁酯，得到淡黄色油状液体苄基(3-甲苯基)硫醚的产率为89％。
1H NMR(400MHz,CDCl3)δ7.26–6.98(m,8H),6.91(s,1H),4.02(s,2H),2.20(s,3H).
实施例十二
用3-(溴苯-4-亚磺酰基)-丙酸叔丁酯代替实施例一中的3-(甲苯-4-亚磺酰基)-丙酸叔丁酯，得到白色固体苄基(4-溴苯基)硫醚的产率为89％。
1H NMR(400MHz,CDCl3)δ7.31–7.12(m,7H),7.06(d,J＝8.5Hz,2H),4.00(s,2H).
实施例十三
用3-(甲苯-2-亚磺酰基)-丙酸叔丁酯代替实施例一中的3-(甲苯-4-亚磺酰基)-丙酸叔丁酯，得到无色油状液体苄基(2-甲苯基)硫醚的产率为87％。
1H NMR(400MHz,CDCl3)δ7.24–6.96(m,9H),3.99(s,2H),2.23(s,3H).实施例十四
用3-(氯苯-4-亚磺酰基)-丙酸叔丁酯代替实施例一中的3-(甲苯-4-亚磺酰基)-丙酸叔丁酯，得到白色固体苄基(4-氯苯基)硫醚的产率为89％。
1H NMR(400MHz,CDCl3)δ7.24–7.10(m,9H),4.00(s,2H).
实施例十五
用3-(氟苯-2-亚磺酰基)-丙酸叔丁酯代替实施例一中的3-(甲苯-4-亚磺酰基)-丙酸叔丁酯，得到淡黄色油状液体苄基(2-氟苯基)硫醚的产率为88％。
1H NMR(400MHz,CDCl3)δ7.23–7.07(m,7H),6.95(ddd,J＝7.9,7.5,4.8Hz,2H),4.02(s,2H).
实施例十六
用3-(甲氧基苯-4-亚磺酰基)-丙酸叔丁酯代替实施例一中的3-(甲苯-4-亚磺酰基)-丙酸叔丁酯，得到白色固体苄基(4-甲氧基苯基)硫醚的产率为89％。
1H NMR(400MHz,CDCl3)δ7.24–7.05(m,7H),6.75–6.66(m,2H),3.90(s,2H),3.69(s,3H).
实施例十七
用3-(苯并噻唑基-2-亚磺酰基)-丙酸叔丁酯代替实施例一中的3-(甲苯-4-亚磺酰基)-丙酸叔丁酯，得到淡黄色油状液体2-(苄硫基)苯并噻唑的产率为85％。
1H NMR(400MHz,CDCl3)δ7.82(d,J＝8.1Hz,1H),7.69–7.62(m,1H),7.42–7.13(m,7H),4.52(s,2H).
实施例十八
用3-(苯并噁唑基-2-亚磺酰基)-丙酸叔丁酯代替实施例一中的3-(甲苯-4-亚磺酰基)-丙酸叔丁酯，得到白色固体2-(苄硫基)苯并恶唑的产率为86％。
1H NMR(400MHz,CDCl3)δ7.54(dd,J＝7.7,0.9Hz,1H),7.41–7.12(m,8H),4.48(s,2H).
实施例十九
用3-(吡啶基-3-亚磺酰基)-丙酸叔丁酯代替实施例一中的3-(甲苯-4-亚磺酰基)-丙酸叔丁酯，得到淡黄色油状液体3-(苄硫基)吡啶的产率为85％
1H NMR(400MHz,CDCl3)δ8.45(d,J＝2Hz,1H),8.35(dd,J1＝1.2Hz,J2＝4.8Hz,1H),7.47-7.50(m,1H),7.16-7.21(m,5H),7.08(dd,J1＝4.7Hz,J2＝7.6Hz,1H)
实施例二十
3-(环戊基亚磺酰基)-丙酸叔丁酯代替实施例一中的3-(甲苯-4-亚磺酰基)-丙酸叔丁酯，得到淡黄色油状液体苄基(环戊基)硫醚的产率为86％。
1H NMR(400MHz,CDCl3)δ7.34–7.16(m,5H),3.72(s,1H),2.94(p,J＝6.8Hz,1H),1.99–1.85(m,2H),1.74–1.67(m,2H),1.59–1.42(m,4H)
实施例二十一
3-(丁基亚磺酰基)-丙酸叔丁酯代替实施例一中的3-(甲苯-4-亚磺酰基)-丙酸叔丁酯，得到无色油状液体苄基(丁基)硫醚的产率为86％。
1H NMR(400MHz,CDCl3)δ0.89(t,J＝7.1Hz,3H),1.33–1.55(m,4H),2.43(t,J＝7.5Hz,2H),3.85(s,2H),7.01–7.43(m,5H)
实施例二十二
N,N,N-三甲基-1-苯基乙基三氟甲烷磺酸铵代替实施例一中的N,N,N-三甲基苄基三氟甲烷磺酸铵，得到淡黄色液体(1-苯乙基)(对甲苯基)硫醚产率为85％。
1H NMR(400MHz,CDCl3)δ7.28-7.22(m,4H),7.22-7.15(m,3H),7.01(d,J＝7.9Hz,2H),4.25(q,J＝7.0Hz,1H),2.28(s,3H),1.59(d,J＝7.0Hz,3H)
Figure BDA0002760079330000071
实施例二十三
(R)-N,N,N-三甲基-1-苯基乙基三氟甲烷磺酸铵代替实施例一中的N,N,N-三甲基苄基三氟甲烷磺酸铵，得到淡黄色液体(R)-(1-苯乙基)(对甲苯基)硫醚产率为85％。
Figure BDA0002760079330000072
核磁共振氢谱表征数据同实施例二十二
手性值ee％:95％。
实施例二十四
(S)-N,N,N-三甲基-1-苯基乙基三氟甲烷磺酸铵代替实施例一中的N,N,N-三甲基苄基氟甲烷磺酸铵，得到淡黄色液体(S)-(1-苯乙基)(对甲苯基)硫醚产率为85％。
Figure BDA0002760079330000081
核磁共振氢谱表征数据同实施例二十二
手性值ee％:95％。

Claims (1)

1.一种苄基硫醚的合成方法，其特征在于：在50％氢氧化钾水溶液的作用下，苄基三氟甲烷磺酸季铵盐与β-亚磺酰基酯在乙腈中反应得到苄基硫醚；所述的苄基三氟甲烷磺酸季铵盐为N,N,N-三甲基苄基三氟甲烷磺酸铵，N,N,N-三甲基(2-溴苄基)三氟甲烷磺酸铵，N,N,N-三甲基(4-叔丁基苄基)三氟甲烷磺酸铵，N,N,N-三甲基(2-氟苄基)三氟甲烷磺酸铵，N,N,N-三甲基(3-甲基苄基)三氟甲烷磺酸铵，N,N,N-三甲基(3-甲氧基苄基)三氟甲烷磺酸铵，N,N,N-三甲基(4-三氟甲基苄基)三氟甲烷磺酸铵，N,N,N-三甲基(4-氰基苄基)三氟甲烷磺酸铵，N,N,N-三甲基-1-(萘-1-基)甲基三氟甲磺酸铵，N,N,N-三甲基-1-苯基乙基三氟甲烷磺酸铵，(R)-N,N,N-三甲基-1-苯基乙基三氟甲烷磺酸铵，(S)-N,N,N-三甲基-1-苯基乙基三氟甲烷磺酸铵；所述的β-亚磺酰基酯为3-(甲苯-4-亚磺酰基)-丙酸叔丁酯，3-(甲苯-3-亚磺酰基)-丙酸叔丁酯，3-(溴苯-4-亚磺酰基)-丙酸叔丁酯，3-(甲苯-2-亚磺酰基)-丙酸叔丁酯，3-(氯苯-4-亚磺酰基)-丙酸叔丁酯，3-(氟苯-2-亚磺酰基)-丙酸叔丁酯，3-(甲氧基苯-4-亚磺酰基)-丙酸叔丁酯，3-(苯并噻唑基-2-亚磺酰基)-丙酸叔丁酯，3-(苯并噁唑基-2-亚磺酰基)-丙酸叔丁酯，3-(吡啶基-3-亚磺酰基)-丙酸叔丁酯，3-(环戊基亚磺酰基)-丙酸叔丁酯，3-(丁基亚磺酰基)-丙酸叔丁酯。
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