CN114075108A - 醛的氘代和制备氘代醛中的应用 - Google Patents

醛的氘代和制备氘代醛中的应用 Download PDF

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CN114075108A
CN114075108A CN202010834414.XA CN202010834414A CN114075108A CN 114075108 A CN114075108 A CN 114075108A CN 202010834414 A CN202010834414 A CN 202010834414A CN 114075108 A CN114075108 A CN 114075108A
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汪清民
董建洋
刘玉秀
王兹稳
宋红健
李永强
张静静
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Nankai University
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Abstract

本发明属于精细化学品技术领域，具体涉及可见光与有机小分子协同催化的醛的氘代反应制备氘代醛。醛与光催化剂4CzIPN、有机小分子催化剂三异丙基硅基硫醇((i‑Pr)3SiSH)、碳酸钠(NaCO3)、氘代水和有机溶剂混合，向反应瓶中吹氩气，在36W的470nm蓝光照射下反应。旋去溶剂，柱层析得到纯品。

Description

醛的氘代和制备氘代醛中的应用
技术领域
本发明属于精细化学品技术领域，具体涉及可见光与有机小分子协同催化的醛的氘代反应在制备氘代醛中的应用。
背景技术
氘代作为标记技术在反应机理的研究，药物的吸收、分布、代谢和排泄(ADME)研究，核磁共振光谱和质谱分析研究中具有重要的作用。近年来，在药物分子中引入氘原子，在保持药物基本药理活性的同时，以增强其代谢和药代动力学特性的研究得到快速的发展。醛在药物和有机合成中无处不在，氘代醛可作为理想的氘代合成砌块，用于构建更为复杂的分子结构。氘代醛目前的合成方法包括LiAlD4还原相应的酯后再氧化，Schwartz试剂(由LiAlD4制备)还原相应的酰胺，Pd/Rh-共催化还原羰基化反应，羧酸的脱氧氘代反应。考虑到有机合成中的原子和步骤经济性，制备氘代醛最理想的方法是氢氘交换反应(HIE)。在这一方面，已经报道了两例Ir-和Ru-催化的HIE反应，但是这些反应的氘代率不高且区域选择性不好，往往会得到芳香环碳氢键氘代的副产物。此外，将氘原子引入到结构复杂的醛中也是有机合成中的挑战(E.P.K.Olsen，T.Singh，P.Harris，P.G.Andersson，R.Madsen，J.Am.Chem.Soc.2015，137，834；J.T.Spletstoser，J.M.White，A.R.Tunoori，G.I.Georg，J.Am.Chem.Soc.2007，129，3408；M.Y.S.Ibrahim，S.E.Denmark，Angew.Chem.Int.Ed.2018，57，10362；M.Zhang，X.-A.Yuan，C.-J.Zhu and J.Xie，Angew.Chem.Int.Ed.2019，58，312.W.J.Kerr，M.Reid，T.Tuttle，Angew.Chem.Int.Ed.2017，56，7808；E.S.Isbrandt，J.K.Vandavasi，W.Zhang，M.P.Jamshidi，S.G.Newman，Synlett 2017，28，2851；H.Geng，X.Chen，J.Gui，Y.Zhang，Z.Shen，P.Qian，J.Chen，S.Zhang，W.Wang，Nature Catal.2019，2，1071；W.Liu，L.-L.Zhao，M.Melaimi，L.Cao，X.Xu，J.Bouffard，G.Bertrand，X.Yan，Chem.2019，5，2484.)。
发明内容
本发明的目的是提供芳香醛和脂肪醛醛基碳氢键直接氘代来合成氘代醛的方法。
本发明的可见光与有机小分子协同催化的醛的氘代反应制备氘代醛的合成路线如下(方程式1)。
方程式1：
Figure BSA0000217092350000011
其中醛A包括取代的或未取代的苯，取代的或未取代的吡啶，取代的或未取代的喹啉，取代的或未取代的噻唑，取代的或未取代的吲哚，取代的或未取代的咔唑，取代的或未取代的呋喃，取代的或未取代的苯乙醛，取代的或未取代的苯丙醛，取代的或未取代的苯丁醛，取代的或未取代的苯戊醛，取代的或未取代的2-吡啶乙醛，取代的或未取代的3-吡啶丙醛，取代的或未取代的4-吡啶丁醛等。所述取代的取代基各自独立地选自羟基、卤素、氰基、硝基、酯基、三氟甲基、三氟甲氧基、酰胺基、C1-C6的烃基、C1-C6的烷氧基、C1-C6的烷巯基、C1-C4的烷基取代的羰氧基和C1-C4的烷氧基取代的羰氧基中的一种或多种。
本发明的方法是：将醛A与光催化剂4CzIPN、有机小分子催化剂三异丙基硅基硫醇((i-Pr)3SiSH)、碳酸钠(NaCO3)、氘代水和有机溶剂混合，向反应瓶中吹氩气，在36W的470nm蓝光照射下进行反应。柱层析得到纯品。
本反应中醛、光催化剂4CzIPN、有机小分子催化剂(i-Pr)3SiSH、碳酸钠和氘代水的摩尔比是1∶0.001-0.2∶0.01-1∶0.01-1∶10-200。
反应温度可在-30-80℃范围内进行，反应不需要对光反应器降温，最佳的反应温度为20-50℃。
本反应的反应时间为12-72小时，最佳反应时间为36-48小时。
在本发明中所使用的有机溶剂可以是醇，如乙醇、甲醇等；烷烃或环烷烃，如环己烷、正己烷、正戊烷、正庚烷、石油醚、汽油等；醚，如乙醚、四氢呋喃等；氯代烷烃，如二氯甲烷、三氯甲烷、四氯化碳、1，2-二氯乙烷等；乙酸乙酯，二甲基亚砜，N，N-二甲基甲酰胺，N，N-二甲基乙酰胺，乙腈。最佳的有机溶剂为乙酸乙酯、二氯甲烷。
本反应在不加4CzIPN或不加(i-Pr)3SiSH或不光照的条件下，均不能发生。
本反应可以对复杂的醛类分子和药物进行后期氘代修饰，得到表1中的化合物。其具体包括下述步骤：将复杂的醛类分子或药物与光催化剂4CzIPN、有机小分子催化剂三异丙基硅基硫醇((i-Pr)3SiSH)、碳酸钠(NaCO3)、氘代水和有机溶剂混合，向反应瓶中吹氩气，在36W的470nm蓝光照射下进行反应。柱层析得到纯品。
本反应中醛、光催化剂4CzIPN、有机小分子催化剂(i-Pr)3SiSH、碳酸钠和氘代水的摩尔比是1∶0.001-0.2∶0.01-1∶0.01-1∶10-200。
反应温度可在-30-80℃范围内进行，反应不需要对光反应器降温，最佳的反应温度为20-50℃。
本反应的反应时间为12-72小时，最佳反应时间为36-48小时。
在本发明中所使用的有机溶剂可以是醇，如乙醇、甲醇等；烷烃或环烷烃，如环己烷、正己烷、正戊烷、正庚烷、石油醚、汽油等；醚，如乙醚、四氢呋喃等；氯代烷烃，如二氯甲烷、三氯甲烷、四氯化碳、1，2-二氯乙烷等；乙酸乙酯，二甲基亚砜，N，N-二甲基甲酰胺，N，N-二甲基乙酰胺，乙腈。最佳的有机溶剂为乙酸乙酯、二氯甲烷。
本反应在不加4CzIPN或不加(i-Pr)3SiSH或不光照的条件下，均不能发生。
表1可见光与有机小分子协同催化的醛的氘代反应对复杂的醛分子和药物进行修饰
Figure BSA0000217092350000031
具体实施方式
下述的实施例中，熔点未经校正，收率未经优化。
实施例1：(2S，5R)-2-异丙基-5-甲基环己基3甲酰基苯甲酸酯-甲酰基-d1的合成：
称取0.2mmol(2S，5R)-2-异丙基-5-甲基环己基3甲酰苯甲酸酯，0.01mmol光催化剂4CzIPN，0.08mmol三异丙基硅基硫醇((i-Pr)3SiSH)，0.08mmol碳酸钠(NaCO3)于8mL反应瓶中，再加入1mL乙酸乙酯溶液，1mL氘代水，向反应瓶中吹氩气30s，在36W的470nm蓝光照射下反应36小时，旋去溶剂，柱层析(石油醚∶乙酸乙酯＝20∶1)得到黄色液体，收率88％，氘代率91％。1H NMR(400MHz，CDCl3)δ10.10(s，0.09H)，8.53(s，1H)，8.32(d，J＝7.6Hz，1H)，8.09(d，J＝7.6Hz，1H)，7.64(t，J＝7.6Hz，1H)，5.00(td，J＝10.8，4.4Hz，1H)，2.13(d，J＝12.0Hz，1H)，1.95(dtd，J＝13.6，6.8，2.4Hz，1H)，1.80-1.70(m，2H)，1.65-1.51(m，2H)，1.14(dd，J＝23.2，11.6Hz，2H)，1.03-0.88(m，7H)，0.81(d，J＝6.8Hz，3H).13C NMR(100MHz，CDCl3)δ191.3(t，J＝28Hz)，165.1，136.6(t，J＝3.5Hz)，135.3，133.0，132.0，131.3，129.3，75.6，47.3，41.0，34.3，31.6，26.6，23.6，22.1，20.9，16.5.HRMS(ESI)calcd forC18H24DO3[M+H]+290.1861，found 290.1862.
实施例2：3-(甲酰基-d)苯基2-(4-异丁基苯基)丙酸酯的合成：
称取0.2mmol 3-甲酰基苯基2-(4-异丁基苯基)丙酸酯，0.01mmol光催化剂4CzIPN，0.08mmol三异丙基硅基硫醇((i-Pr)3SiSH)，0.08mmol碳酸钠(NaCO3)于8mL反应瓶中，再加入1mL乙酸乙酯溶液，1mL氘代水，向反应瓶中吹氩气30s，在36W的470nm蓝光照射下反应36小时，旋去溶剂，柱层析(石油醚∶乙酸乙酯＝20∶1)得到黄色液体，收率80％，氘代率93％。1H NMR(400MHz，CDCl3)δ9.95(s，0.07H)，7.71(d，J＝7.6Hz，1H)，7.51(dt，J＝15.6，4.8Hz，2H)，7.35-7.23(m，3H)，7.16(t，J＝6.4Hz，2H)，3.96(q，J＝7.2Hz，1H)，2.47(d，J＝7.2Hz，2H)，1.87(tt，J＝13.2，6.8Hz，1H)，1.61(d，J＝7.2Hz，3H)，0.91(d，J＝6.8Hz，6H).13C NMR(100MHz，CDCl3)δ191.0(t，J＝27.5Hz)，173.0，151.5，141.1，137.6(t，J＝3.5Hz)，136.9，130.1，129.7，127.8，127.4，127.3，122.2，45.3，45.1，30.3，22.5，18.6.HRMS(ESI)calcd for C20H22DO3[M+H]+312.1704，found 312.1706.
实施例3：6-(3-((3r，5r，7r)-金刚烷-1-基)-4-甲氧基苯基)-2萘醛-d1的合成：
称取0.2mmol 6-(3-((3r，5r，7r)-金刚烷-1-基)-4-甲氧基苯基)-2萘醛，0.01mmol光催化剂4CzIPN，0.08mmol三异丙基硅基硫醇((i-Pr)3SiSH)，0.08mmol碳酸钠(NaCO3)于8mL反应瓶中，再加入1mL乙酸乙酯溶液，1mL氘代水，向反应瓶中吹氩气30s，在36W的470nm蓝光照射下反应36小时，旋去溶剂，柱层析(石油醚∶乙酸乙酯＝20∶1)得到白色固体，收率82％，氘代率96％，熔点236-237℃.1H NMR(400MHz，CDCl3)δ10.16(s，0.07H)，8.35(s，1H)，8.04(dd，J＝4.8，3.2Hz，2H)，7.97(s，2H)，7.88-7.81(m，1H)，7.61(d，J＝2.4Hz，1H)，7.56(dd，J＝8.4，2.4Hz，1H)，7.01(d，J＝8.4Hz，1H)，3.91(s，3H)，2.18(s，6H)，2.11(s，3H)，1.81(s，6H).13C NMR(100MHz，CDCl3)δ191.9(t，J＝27Hz)，159.1，142.3，139.1，136.9，134.3，133.7(t，J＝3.1Hz)，132.3，131.4，131.3，129.9，129.8，129.2，126.9，126.0，125.8，125.0，123.2，112.2，55.2，40.6，37.2，37.1，29.1.HRMS(ESI)calcdfor C28H28DO2[M+H]+398.2225，found 398.2224.
用同样的方法可以合成下列氘代醛，但并不限定本发明。
2-萘甲醛-d1：白色固体，收率88％，氘代率93％，熔点86-87℃.1H NMR(400MHz，CDCl3)δ10.16(s，0.07H)，8.33(s，1H)，8.11-7.82(m，4H)，7.76-7.46(m，2H).HRMS(ESI)calcd for C11H8DO[M+H]+158.0711，found 158.0712.
4-氟甲醛-d1：无色液体，收率73％，氘代率96％。1H NMR(400MHz，CDCl3)δ9.97(s，0.04H)，7.99-7.87(m，2H)，7.26-7.15(m，2H).HRMS(ESI)calcd for C7H5DFO[M+H]+126.0460，found 126.0461.
4-氯苯甲醛-d1：白色固体，收率81％，氘代率95％，熔点44-45℃.1H NMR(400MHz，CDCl3)δ9.99(s，0.05H)，7.84(d，J＝8.4Hz，2H)，7.52(d，J＝8.4Hz，2H).HRMS(ESI)calcdfor C7H5DClO[M+H]+142.0164，found 142.0164.
4-溴苯甲醛-d1：白色固体，收率62％，氘代率95％，熔点76-77℃.1H NMR(400MHz，CDCl3)δ9.98(s，0.05H)，7.76(d，J＝8.4Hz，2H)，7.69(d，J＝8.4Hz，2H).HRMS(ESI)calcdfor C7H5DBrO[M+H]+185.9659，found 185.9660
4-碘苯甲醛-d1：白色固体，收率83％，氘代率90％，熔点98-99℃.1H NMR(400MHz，CDCl3)δ9.98(s，0.1H)，7.94(d，J＝8.4Hz，2H)，7.62(d，J＝8.4Hz，2H).HRMS(ESI)calcdfor C7H5DIO[M+H]+233.9521，found 233.9518.
4-叔丁基甲醛-d1：无色液体，收率89％，氘代率99％。1H NMR(400MHz，CDCl3)δ9.98(s，0.01H)，7.82(d，J＝8.0Hz，2H)，7.55(d，J＝8.0Hz，2H)，1.36(s，9H).HRMS(ESI)calcdfor C11H14DO[M+H]+164.1180，found 164.1181.
3，4-二甲基苯甲醛-d1：无色液体，收率75％，氘代率99％。1H NMR(400MHz，CDCl3)δ9.93(s，0.01H)，7.80-7.52(m，2H)，7.28(d，J＝7.6Hz，1H)，2.46-2.19(m，6H).HRMS(ESI)calcd for C9H10DO[M+H]+136.0867，found 136.0867.
3-甲基-4-氟苯甲醛-d1：无色液体，收率79％，氘代率99％。1H NMR(400MHz，CDCl3)δ9.93(s，0.01H)，7.80-7.69(m，2H)，7.15(t，J＝8.8Hz，1H)，2.35(d，J＝2.0Hz，3H).HRMS(ESI)calcd for C8H7DFO[M+H]+140.0616，found 140.0616.
3，5-二叔丁基苯甲醛-d1：无色液体，收率72％，氘代率99％。1H NMR(400MHz，CDCl3)δ10.01(s，0.01H)，7.77-7.69(m，2H)，7.26(s，1H)，1.37(s，18H).HRMS(ESI)calcdfor C15H22DO[M+H]+220.1806，found 220.1808.
(3-甲酰基苯基)氨基甲酸叔丁酯-d1：白色固体，收率91％，氘代率99％，熔点88-89℃.1H NMR(400MHz，CDCl3)δ9.98(s，0.01H)，7.94(s，1H)，7.64(d，J＝7.6Hz，1H)，7.56(d，J＝7.6Hz，1H)，7.45(t，J＝7.6Hz，1H)，6.78(s，1H)，1.53(s，9H).HRMS(ESI)calcd forC12H15DNO3[M+H]+223.1187，found 223.1186.
4-甲巯基苯甲醛-d1：无色液体，收率76％，氘代率99％。1H NMR(400MHz，CDCl3)δ9.92(s，0.01H)，7.77(d，J＝8.0Hz，2H)，7.32(d，J＝8.0Hz，2H)，2.53(s，3H).HRMS(ESI)calcd for C8H8DOS[M+H]+154.0431，found 154.0431.
4-二甲胺基苯甲醛-d1：白色固体，收率93％，氘代率98％，熔点67-69℃.1H NMR(400MHz，CDCl3)δ9.73(s，0.02H)，7.73(d，J＝8.8Hz，2H)，6.68(d，J＝8.8Hz，2H)，3.09-3.02(m，0.18H).HRMS(ESI)calcd for C9H5D7NO[M+H]+157.1353，found 157.1356.
苯并[d][1，3]二恶唑-5-甲醛-d1：无色液体，收率74％，氘代率99％。1H NMR(400MHz，CDCl3)δ9.81(s，0.01H)，7.42(d，J＝8.0Hz，1H)，7.34(s，1H)，6.94(d，J＝8.0Hz，1H)，6.13-6.01(m，1.66H).HRMS(ESI)calcd for C8H6DO3[M+H]+152.0452，found152.0454.
2，3-二氢苯并[b][1，4]二恶英-6-甲醛-d1：白色固体，收率91％，氘代率99％，熔点44-45℃.1H NMR(400MHz，CDCl3)δ9.82(s，0.01H)，7.40(dd，J＝4.4，2.4Hz，2H)，6.98(d，J＝8.8Hz，1H)，4.36-4.32(m，2H)，4.31-4.27(m，2H).HRMS(ESI)calcd for C9H8DO3[M+H]+166.0609，found 166.0610.
3-(4，4，5，5-四甲基-1，3，2-二氧杂硼烷-2-基)苯甲醛-d1：无色液体，收率79％，氘代率98％。1H NMR(400MHz，CDCl3)δ10.05(s，0.02H)，8.31(s，1H)，8.06(d，J＝7.2Hz，1H)，8.03-7.95(m，1H)，7.53(t，J＝7.6Hz，1H)，1.37(s，12H).HRMS(ESI)calcd for C13H17DBO3[M+H]+234.1406，found 234.1403.
2，6-二叔丁基-4-羟基苯甲醛-d1：白色固体，收率89％，氘代率90％，熔点136-137℃.1H NMR(400MHz，CDCl3)δ9.86(s，0.1H)，7.74(s，2H)，5.88(s，1H)，1.48(s，18H).HRMS(ESI)calcd for C15H22DO2[M+H]+236.1755，found 236.1756.
2，6-二氯苯甲醛-d1：白色固体，收率49％，氘代率99％，熔点54-55℃.1H NMR(400MHz，CDCl3)δ10.50(s，0.01H)，7.40(s，3H).HRMS(ESI)calcd for C7H4DCl2O[M+H]+175.9775，found 175.9776.
1-甲苯基-1H-吲哚-5-甲醛-d1：白色固体，收率71％，氘代率99％，熔点120-121℃.1H NMR(400MHz，CDCl3)δ10.03(s，0.01H)，8.11(d，J＝8.4Hz，1H)，8.07(s，1H)，7.86(dd，J＝8.4，1.2Hz，1H)，7.79(d，J＝8.4Hz，2H)，7.68(d，J＝3.6Hz，1H)，7.26(d，J＝8.0Hz，2H)，6.78(d，J＝3.6Hz，1H)，2.35(s，3H).HRMS(ESI)calcd for C16H13DNO3S[M+H]+301.0752，found 301.0750.
9-乙基-9H-咔唑-3-甲醛-d1：白色固体，收率87％，氘代率99％，熔点84-85℃.1HNMR(400MHz，CDCl3)δ10.04(s，0.01H)，8.53(d，J＝3.6Hz，1H)，8.15-8.05(m，1H)，8.00-7.91(m，1H)，7.50(t，J＝7.6Hz，1H)，7.39(dd，J＝9.2，5.6Hz，2H)，7.29(t，J＝7.6Hz，1H)，4.41-4.22(m，2H)，1.49-1.35(m，3H).HRMS(ESI)calcd for C15H13DNO[M+H]+225.1133，found 225.1134.
3-(苯并[d][1，3]二氧杂-5-基)-2-甲基丙醛-d1：无色液体，收率74％，氘代率99％。1H NMR(400MHz，CDCl3)δ9.70(d，J＝1.6Hz，0.01H)，6.73(d，J＝8.0Hz，1H)，6.66(d，J＝1.6Hz，1H)，6.61(dd，J＝8.0，1.6Hz，1H)，5.93(s，1.72H)，3.00(dd，J＝13.6，5.6Hz，1H)，2.67-2.47(m，2H)，1.08(d，J＝6.8Hz，3H).HRMS(ESI)calcd for C11H12DO3[M+H]+194.0922，found 194.0924.
3-(苯并[d][1，3]二氧杂-5-基)-2，2-二甲基丙醛-d1：无色液体，收率79％，氘代率100％。1H NMR(400MHz，CDCl3)δ6.71(d，J＝7.6Hz，1H)，6.64(s，1H)，6.58(d，J＝7.6Hz，1H)，5.91(s，1.72H)，2.38(s，2H)，0.88(s，6H).HRMS(ESI)calcd for C12H14DO3[M+H]+208.1078，found 208.1080.
3-(4-异丙基苯基)-2-甲基丙醛-d1：无色液体，收率85％，氘代率99％。1H NMR(400MHz，CDCl3)δ9.72(d，J＝1.6Hz，0.01H)，7.16(d，J＝8.0Hz，2H)，7.09(d，J＝8.0Hz，2H)，3.04(dt，J＝11.2，5.6Hz，1H)，2.88(dt，J＝13.6，6.8Hz，1H)，2.67(dt，J＝12.8，6.8Hz，1H)，2.61-2.51(m，1H)，1.24(d，J＝6.8Hz，6H)，1.09(d，J＝6.8Hz，3H).HRMS(ESI)calcd for C13H18DO[M+H]+192.1493，found 192.1494.
上述实施例中所合成的化合物为以下结构所示的化合物：
Figure BSA0000217092350000061

Claims (7)

1.可见光与有机小分子协同催化的醛的氘代反应制备氘代醛的方法，其特征是将1当量的醛与0.1-20mmol％的光催化剂4CzIPN、1-100mmol％的有机小分子催化剂三异丙基硅基硫醇((i-Pr)3SiSH)、1-100mmol％的碳酸钠(NaCO3)、10-200当量的氘代水和溶剂混合，向反应瓶中吹氩气，在36W的470nm蓝光照射下反应，旋去溶剂，柱层析得到纯品，
Figure FSA0000217092340000011
其中醛A包括取代的或未取代的苯，取代的或未取代的吡啶，取代的或未取代的喹啉，取代的或未取代的噻唑，取代的或未取代的吲哚，取代的或未取代的咔唑，取代的或未取代的呋喃，取代的或未取代的苯乙醛，取代的或未取代的苯丙醛，取代的或未取代的苯丁醛，取代的或未取代的苯戊醛，取代的或未取代的2-吡啶乙醛，取代的或未取代的3-吡啶丙醛，取代的或未取代的4-吡啶丁醛等。所述取代的取代基各自独立地选自羟基、卤素、氰基、硝基、酯基、三氟甲基、三氟甲氧基、酰胺基、C1-C6的烃基、C1-C6的烷氧基、C1-C6的烷巯基、C1-C4的烷基取代的羰氧基和C1-C4的烷氧基取代的羰氧基中的一种或多种。
2.可见光与有机小分子协同催化的醛的氘代反应对复杂的醛分子和药物进行氘代修饰的方法，将1当量的复杂的醛分子或药物与0.1-20mmol％的光催化剂4CzIPN、1-100mmol％的有机小分子催化剂三异丙基硅基硫醇((i-Pr)3SiSH)、1-100mmol％的碳酸钠(NaCO3)、10-200当量的氘代水和溶剂混合，向反应瓶中吹氩气，在36W的470nm蓝光照射下反应，旋去溶剂，柱层析得到纯品1-11，
Figure FSA0000217092340000021
3.权利要求1或2所述的合成方法，其特征在于所述的醛、光催化剂4CzIPN、有机小分子催化剂(i-Pr)3SiSH、碳酸钠和氘代水的摩尔比是1∶0.001-0.2∶0.01-1∶0.01-1∶10-200。
4.权利要求1或2所述的合成方法，其特征在于有机溶剂可以是乙醇、甲醇、环己烷、正己烷、正戊烷、正庚烷、石油醚、乙醚、四氢呋喃、二氯甲烷、三氯甲烷、四氯化碳、1，2-二氯乙烷等、乙酸乙酯、二甲基亚砜、N，N-二甲基甲酰胺、N，N-二甲基乙酰胺、乙腈中的一种或多种。
5.按照权利要求1或2所述的合成方法，其特征在于最佳反应溶剂为乙酸乙酯。
6.按照权利要求1或2所述的合成方法，其特征在于所述的反应时间为12-72小时，最佳反应时间为36-48小时。
7.按照权利要求1或2所述的合成方法，其特征在于所述的最佳反应温度为20-50℃。
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CN114805002A (zh) * 2022-06-06 2022-07-29 遵义医科大学 一种还原或氘代还原芳香族烯烃、醛或酮的方法
CN114805002B (zh) * 2022-06-06 2023-08-22 遵义医科大学 一种还原或氘代还原芳香族烯烃、醛或酮的方法

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