CN105712851B - 一种含β-萘基二芳酮化合物的制备方法 - Google Patents
一种含β-萘基二芳酮化合物的制备方法 Download PDFInfo
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- -1 betanaphthyl Chemical group 0.000 title claims abstract description 22
- 150000001875 compounds Chemical class 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- XMWGTKZEDLCVIG-UHFFFAOYSA-N 1-(chloromethyl)naphthalene Chemical compound C1=CC=C2C(CCl)=CC=CC2=C1 XMWGTKZEDLCVIG-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000003513 alkali Substances 0.000 claims abstract description 7
- 239000007800 oxidant agent Substances 0.000 claims abstract description 7
- 230000001590 oxidative effect Effects 0.000 claims abstract description 7
- 239000003446 ligand Substances 0.000 claims abstract description 6
- 239000003863 metallic catalyst Substances 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 25
- 229910052763 palladium Inorganic materials 0.000 claims description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 9
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 8
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
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- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
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- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 150000003003 phosphines Chemical class 0.000 claims description 5
- 239000012312 sodium hydride Substances 0.000 claims description 5
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 3
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- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims description 3
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- 239000012286 potassium permanganate Substances 0.000 claims description 2
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- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
本发明属于医药化工中间体及相关化学技术领域，涉及到新颖的β‑萘基二芳酮化合物的制备方法。其特征是以1‑氯甲基萘及其衍生物为原料，在金属催化剂、配体和碱的作用下，于无水有机溶剂中与苯乙腈类化合物反应，再在氧化剂的作用下转化为含β‑萘基二芳酮类化合物。本发明所述的二芳酮类化合物的制备方法，反应步骤少，原料价格低廉，反应条件温和，便于操作；并且所得产品收率高、纯度高，完全符合作为药物中间体的质量要求，为其工业化生产提供了有利条件。
Description
技术领域
本发明属于医药化工中间体及相关化学技术领域，涉及到新颖的β-萘基二芳酮化合物的制备方法。
背景技术
二芳酮化合物是合成天然产物、有机功能材料等的重要反应中间体。高效、高选择性地合成二芳酮化合物具有重要的现实意义和应用价值。
二芳酮化合物的合成方法主要是Friedel-Crafts酰基化反应[Sartori,G.,Maggi,R.Chem.Rev.,2006,106,1077]与插羰偶联反应[Wu,X.F.,Neumann,H.,Beller,M.Chem.Soc.Rev.,2011,40,4986]，前者反应温度高、区域选择性差；后者需要使用有毒CO气体。目前，经由C-H键活化官能化的方法已经成为研究热点，然而定位基的使用限制了底物的范围。因此，开发更加高效、便捷的二芳酮的合成方法具有重要意义。
作为最传统的酰基化方法，Friedel–Crafts酰基化反应是工业上应用最广的方法。该方法的区域选择性较差，对于1-甲基萘的底物来说，4-位酰基化反应较容易发生，而2-位酰基化反应则不易实现，除非4-位被取代基占据。
插羰偶联酰基化的方法，除了需要使用CO作为酰基源，芳环上一般需要有预官能化的卤素原子，而在1-甲基萘的2-位连接卤素同样是反应的难点。
sp2碳–氢键直接酰基化反应是合成二芳酮的一种原子经济性好、区域选择性高的方法[Xu,B.,Liu,W.,Kuang,C.X.Eur.J.Org.Chem.,2014,12,2576]。目前，在定位基的作用下，使用不同种类的酰基源，可以实现芳环2-位酰基化的反应，合成二芳酮类化合物。定位基的使用会限制底物的适用范围，如何将定位基移除或者转换是该方法需要面临的问题。
发明内容
本发明提供了一种新颖的β-萘基二芳酮化合物的制备方法，该方法的合成路线短、底物易得、条件温和、便于操作，并且收率较高。
本发明的技术方案：
一种含β-萘基二芳酮化合物的制备方法，以1-氯甲基萘衍生物为原料，在碱、金属催化剂和配体的作用下与苯乙腈类化合物反应，于无水有机溶剂中与苯乙腈类化合物在20℃～100℃条件下，反应12小时；将所生成产物在氧化剂的作用下转化为二芳酮类化合物，合成路线如下：
R1＝H，alkyl R3＝H，Br，CO2Me，Me，NO2
R2＝H，Me，OMe，Ph，halide R4＝H，halids，Ph，OMe，alkyl
R1选自氢(H),烷基(alkyl)；
R2选自氢(H),甲基(Me),甲氧基(OMe),苯基(Ph),卤素(halides)；
R3选自氢(H),溴(Br),碳酸甲酯基(CO2Me),甲基(Me),硝基(NO2)；
R4选自氢(H),卤素(halides),苯基(Ph),甲氧基(OMe),烷基(alkyl)；
1-氯甲基萘衍生物与碱的摩尔比为1:1～1:20；
1-氯甲基萘衍生物与金属催化剂的摩尔比为1:0.05～1:0.1；
1-氯甲基萘衍生物与苯乙腈类化合物的摩尔比为1:1～1:50；
1-氯甲基萘衍生物与氧化剂的摩尔比为1:2～1:50；
1-氯甲基萘衍生物的摩尔浓度为0.01mmol/mL～2mmol/mL。
溶剂包括：四氢呋喃、乙二醇二甲醚、二氯甲烷、乙醚、二甲基亚砜、四氯化碳、甲苯、N,N-二甲基甲酰胺、正己烷等，优选四氢呋喃、乙二醇二甲醚、1,4-二氧六环。
碱包括：氢氧化钾、碳酸钠、碳酸钾、碳酸氢钠、氢化钠、醋酸钠、甲醇钠、磷酸三钾、叔丁醇钠、碳酸铯。优选氢化钠、叔丁醇钠、甲醇钠。
金属催化剂包括：二(乙酰丙酮)钯、二(三苯基膦)二氯化钯、三(二亚苄基丙酮)二钯、醋酸钯、三氟乙酸钯、氯化钯、二(乙腈)二氯化钯、双(二苯基膦)二茂铁二氯化钯二氯甲烷加合物。优选三(二亚苄基丙酮)二钯、氯化钯、醋酸钯、双(二苯基膦)二茂铁二氯化钯二氯甲烷加合物。
配体包括：三(3,5-双三氟甲基苯基)膦、三(2-呋喃基)膦、三环己基膦、三甲基膦、三乙基膦、二甲基苯基膦、三正丁基膦。优选三(3,5-双三氟甲基苯基)膦、三乙基膦、二甲基苯基膦、三正丁基膦。
氧化剂包括：过碳酸钠、双氧水、过二硫酸钾、高锰酸钾、二氧化锰、过氧化钠、过氧化二叔丁基、氧气、空气。优选过碳酸钠、氧气、空气。
分离方法包括：重结晶、柱层析等。重结晶方法使用的溶剂如，苯、乙醇、石油醚、乙腈、四氢呋喃、氯仿、正己烷、丙酮、乙酸乙酯、二氯甲烷；用柱层析方法，可以使用硅胶或氧化铝作为固定相，展开剂一般为极性与非极性的的混合溶剂，如乙酸乙酯-石油醚、乙酸乙酯-正己烷、二氯甲烷-石油醚、甲醇-石油醚。
本发明的制备方法，合成路线短、条件温和、操作简便、有实现工业化的可能性，并且较高收率得到β-二芳酮产物；该方法可以得到萘甲基结构，从而近一步官能化，得到药物中间体、光学材料等功能性分子。
附图说明
图1是实施例1中(1’-甲基-4’-甲氧基-2’-萘基)-苯甲酮的1H核磁谱图。
图2是实施例1中(1’-甲基-4’-甲氧基-2’-萘基)-苯甲酮的13C核磁谱图。
图3是实施例2中(1’-甲基-4’-溴-2’-萘基)-苯甲酮的1H核磁谱图。
图4是实施例2中(1’-甲基-4’-溴-2’-萘基)-苯甲酮的13C核磁谱图。
图5是实施例3中(1’-甲基-2’-萘基)-苯甲酮的1H核磁谱图。
图6是实施例3中(1’-甲基-2’-萘基)-苯甲酮的13C核磁谱图。
图7是实施例4中(1’-甲基-2’-萘基)-2-甲基-1-苯甲酮的1H核磁谱图。
图8是实施例4中(1’-甲基-2’-萘基)-2-甲基-1-苯甲酮的13C核磁谱图。
图9是实施例5中(1’-甲基-2’-萘基)-4-叔丁基-1-苯甲酮的1H核磁谱图。
图10是实施例6中(1’-甲基-2’-萘基)-4-溴-1-苯甲酮的1H核磁谱图。
图11是实施例6中(1’-甲基-2’-萘基)-4-溴-1-苯甲酮的13C核磁谱图。
图12是实施例7中(1’-甲基-2’-萘基)-4-氯-1-苯甲酮的1H核磁谱图。
图13是实施例7中(1’-甲基-2’-萘基)-4-氯-1-苯甲酮的13C核磁谱图。
具体实施方式
本发明所述的含β-萘基二芳酮化合物的制备方法，反应步骤较少，原料价格低廉，反应条件温和，便于操作；并且所得产品收率高、纯度高、完全符合作为药物中间体的质量要求，为其工业化生产提供了有利条件。
下面结合具体实施例，进一步阐述本发明。
实施例1：(1’-甲基-4’-甲氧基-2’-萘基)-苯甲酮的合成
在25mL反应器中，加入氢化钠(0.024g,0.6mmol)和醋酸钯(0.003g，0.015mmol)和三(3,5-双三氟甲基苯基)膦(0.020g，0.030mmol)，氮气置换3次后，加入无水1,4-二氧六环5mL，搅拌下加入苯乙腈(0.070g,0.6mmol)和4-甲氧基-1-氯甲基萘(0.062g,0.3mmol)，25℃下搅拌12h后，将反应液在空气中继续搅拌10h。柱层析(硅胶，200-300目；展开剂，石油醚：乙酸乙酯＝20:1)得到(1’-甲基-4’-甲氧基-2’-萘基)-苯甲酮0.063g，产率76％。
(1’-甲基-4’-甲氧基-2’-萘基)-苯甲酮
淡黄色固体，mp 82.8-83.3℃；IR(KBr)ν3068,2934,2844,1667,1595,1510,1450,1371,1347,1275,1239,1112,937,810,763,720cm-1；1H NMR(400MHz,CDCl3)δ2.47(s,3H),3.94(s,3H),6.70(s,1H),7.45(dd,J＝7.6,7.6Hz,2H),7.54–7.63(m,3H),7.86(d,J＝7.2Hz,2H),8.03(d,J＝7.6Hz,1H),8.34(d,J＝8.0Hz,1H)；13C NMR(100MHz,CDCl3)δ16.0,55.7,102.7,122.7,124.2,124.6,126.2,126.4,127.3,128.8,130.3,133.6,133.7,136.3,137.8,153.8,199.7；HRMS(EI,m/z)calcd for C19H16O2:276.1150[M]+；found:276.1151.
实施例2：(1’-甲基-4’-溴-2’-萘基)-苯甲酮的合成
操作同实施例1，由4-甲氧基-1-氯甲基萘与苯乙腈反应得到(1’-甲基-4’-溴-2’-萘基)-苯甲酮0.046g，产率47％。
(1’-甲基-4’-溴-2’-萘基)-苯甲酮
黄色固体，mp 96.7-97.1℃；IR(KBr)ν3068,2924,1668,1596,1449,1325,1270,1244,1176,943,903,801,757,725cm-1；1H NMR(400MHz,CDCl3)δ2.56(s,3H),7.47(dd,J＝7.6,8.0Hz,2H),7.59–7.71(m,4H),7.83(d,J＝6.8Hz,2H),8.12(d,J＝8.0Hz,1H),8.32(d,J＝8.0Hz,1H)；13C NMR(100MHz,CDCl3)δ16.6,121.0,125.3,127.7,128.1,128.3,128.4,128.9,130.4,132.4,132.8,133.9,134.1,137.1,137.4,197.9；HRMS(EI,m/z)calcd forC18H13OBr:324.0150[M]+；found:324.0154.实施例3：(1’-甲基-2’-萘基)-苯甲酮的合成
在25mL反应器中，加入氢化钠(0.048g,1.2mmol)和醋酸钯(0.003g，0.015mmol)和三乙基膦(0.004g，0.030mmol)，氮气置换3次后，加入无水四氢呋喃5mL，搅拌下加入苯乙腈(0.070g,0.6mmol)和1-氯甲基萘(0.053g,0.3mmol)，40℃下搅拌12h后，将反应液加入0.073g过碳酸钠继续搅拌10h。柱层析(硅胶，200-300目；展开剂，石油醚：乙酸乙酯＝100:1)得到(1’-甲基-2’-萘基)-苯甲酮0.040g，产率54％。
(1’-甲基-2’-萘基)-苯甲酮
淡黄色油状液体；IR(neat)ν3056,2924,1665,1595,1448,1277,1248,1167,933,813,750,719cm-1；1H NMR(400MHz,CDCl3)δ2.61(s,3H),7.37(d,J＝8.4Hz,1H),7.45(dd,J＝7.2,8.0Hz,2H),7.55–7.63(m,3H),7.77(d,J＝8.4Hz,1H),7.84(dd,J＝1.2,8.0Hz,2H),7.89(dd,J＝2.4,7.6Hz,1H),8.12(d,J＝7.6Hz,1H)；13C NMR(100MHz,CDCl3)δ16.5,124.79,124.84,126.3,126.87,126.93,128.7,128.8,130.4,132.8,132.9,133.5,134.0,136.6,137.9,199.6；HRMS(EI,m/z)calcd for C18H14O:246.1045[M]+；found:246.1042.
实施例4：(1’-甲基-2’-萘基)-2-甲基-1-苯甲酮的合成
操作同实施例3，由1-氯甲基萘与2-甲基苯乙腈反应得到(1’-甲基-2’-萘基)-2-甲基-1-苯甲酮0.046g，产率59％。
(1’-甲基-2’-萘基)-2-甲基-1-苯甲酮
白色固体，mp 64.9-65.4℃；IR(KBr)ν3055,2925,1662,1597,1569,1453,1242,930,820,773,751,737cm-1；1H NMR(400MHz,CDCl3)δ2.57(s,3H),2.67(s,3H),7.16(dd,J＝7.2,7.6Hz,1H),7.30–7.42(m,4H),7.54–7.61(m,2H),7.71(d,J＝8.8Hz,1H),7.87(d,J＝7.2Hz,1H),8.14(d,J＝7.6Hz,1H)；13C NMR(100MHz,CDCl3)δ16.1,21.2,125.0,125.4,125.6,126.1,126.7,127.0,128.6,131.5,131.7,131.8,132.8,134.0,134.1,137.5,138.5,139.1,201.6；HRMS(EI,m/z)calcd for C19H16O:260.1201[M]+；found:260.1206.
实施例5：(1’-甲基-2’-萘基)-4-叔丁基-1-苯甲酮的合成
操作同实施例3，由1-氯甲基萘与4-叔丁基苯乙腈反应得到(1’-甲基-2’-萘基)-4-叔丁基-1-苯甲酮0.059g，产率65％。
(1’-甲基-2’-萘基)-4-叔丁基-1-苯甲酮
淡黄色油状液体；IR(neat)ν3054,2963,2905,2868,1663,1604,1463,1278,1253,1169,1108,936,812,771,748cm-1；1H NMR(400MHz,CDCl3)δ1.34(s,9H),2.61(s,3H),7.36(d,J＝8.4Hz,1H),7.45(d,J＝8.8Hz,2H),7.53–7.61(m,2H),7.74–7.79(m,3H),7.88(d,J＝7.6Hz,1H),8.11(d,J＝8.0Hz,1H)；13C NMR(100MHz,CDCl3)δ16.4,31.4,35.4,124.76,124.81,125.7,126.1,126.8,128.8,130.4,132.6,132.8,133.9,135.2,136.9,157.4,199.2；HRMS(EI,m/z)calcd for C22H22O:302.1671[M]+；found:302.1676.
实施例6：(1’-甲基-2’-萘基)-4-溴-1-苯甲酮的合成
在25mL反应器中，加入叔丁醇钠(0.115g,1.2mmol)、双(二苯基膦)二茂铁二氯化钯二氯甲烷加合物(0.012g，0.015mmol)和二甲基苯基膦(0.004g，0.030mmol)，氮气置换3次后，加入无水1,4-二氧六环5mL，搅拌下加入4-溴苯乙腈(0.088g,0.45mmol)和1-氯甲基萘(0.053g,0.3mmol)，60℃下搅拌12h后，向反应液中通入氧气继续搅拌10h，柱层析(硅胶，200-300目；展开剂，石油醚：乙酸乙酯＝100:1)再使用正己烷重结晶得到(1’-甲基-2’-萘基)-4-溴-1-苯甲酮0.037g，产率38％。
(1’-甲基-2’-萘基)-4-溴-1-苯甲酮
白色固体，mp 130.6-131.1℃；IR(KBr)ν3053,1660,1582,1276,1247,1165,1068,1008,934,810,757cm-1；1H NMR(400MHz,CDCl3)δ2.60(s,3H),7.34(d,J＝8.4Hz,1H),7.56–7.63(m,4H),7.69(d,J＝8.8Hz,2H),7.77(d,J＝8.4Hz,1H),7.89(d,J＝7.2Hz,1H),8.11(d,J＝7.6Hz,1H)；13C NMR(100MHz,CDCl3)δ16.5,124.6,124.9,126.4,127.0,127.1,128.8,128.9,131.8,132.1,132.8,133.0,134.1,135.9,136.7,198.5；HRMS(EI,m/z)calcdfor C18H13OBr:324.0150[M]+；found:324.0142.
实施例7：(1’-甲基-2’-萘基)-4-氯-1-苯甲酮的合成
操作同实施例3，由1-氯甲基萘与4-氯苯乙腈反应得到(1’-甲基-2’-萘基)-4-氯-1-苯甲酮0.038g，产率45％。
(1’-甲基-2’-萘基)-4-氯-1-苯甲酮
白色固体，mp 128.8-129.3℃；IR(KBr)ν3056,1659,1583,1277,1248,1089,935,811,759cm-1；1H NMR(400MHz,CDCl3)δ2.60(s,3H),7.35(d,J＝8.4Hz,1H),7.43(d,J＝8.4Hz,2H),7.56–7.64(m,2H),7.77(d,J＝8.4Hz,3H),7.90(d,J＝7.6Hz,1H),8.12(d,J＝7.6Hz,1H)；13C NMR(100MHz,CDCl3)δ16.5,124.6,124.9,126.4,127.0,127.1,128.9,129.1,131.7,132.8,133.0,134.1,136.0,136.3,140.1,198.3；IR(KBr)3056,1659,1583,1277,1248,1089,935,811,759；HRMS(EI,m/z)calcd for C18H13OCl:280.0655[M]+；found:280.0659。
Claims (2)
1.一种含β-萘基二芳酮化合物的制备方法，以1-氯甲基萘衍生物为原料，在碱、金属催化剂和配体的作用下与苯乙腈类化合物反应，于无水有机溶剂中与苯乙腈类化合物在20℃～100℃条件下，反应12小时；将所生成产物在氧化剂的作用下转化为二芳酮类化合物，合成路线如下：
R1选自氢(H),烷基(alkyl)；
R2选自氢(H),甲基(Me),甲氧基(OMe),苯基(Ph),卤素(halides)；
R3选自氢(H),溴(Br),碳酸甲酯基(CO2Me),甲基(Me),硝基(NO2)；
R4选自氢(H),卤素(halides),苯基(Ph),甲氧基(OMe),烷基(alkyl)；
1-氯甲基萘衍生物与碱的摩尔比为1:1～1:20；
1-氯甲基萘衍生物与金属催化剂的摩尔比为1:0.05～1:0.1；
1-氯甲基萘衍生物与苯乙腈类化合物的摩尔比为1:1～1:50；
1-氯甲基萘衍生物与氧化剂的摩尔比为1:2～1:50；
1-氯甲基萘衍生物的摩尔浓度为0.01mmol/mL～2mmol/mL；
所述的碱为氢氧化钾、碳酸钠、碳酸钾、碳酸氢钠、氢化钠、醋酸钠、甲醇钠、磷酸三钾、叔丁醇钠、碳酸铯；
所述的金属催化剂为二(乙酰丙酮)钯、二(三苯基膦)二氯化钯、三(二亚苄基丙酮)二钯、醋酸钯、三氟乙酸钯、氯化钯、二(乙腈)二氯化钯、双(二苯基膦)二茂铁二氯化钯二氯甲烷加合物；
所述的配体为三苯基膦、三(3,5-双三氟甲基苯基)膦、三(2-呋喃基)膦、三环己基膦、三甲基膦、三乙基膦、二甲基苯基膦、三正丁基膦，所述的金属催化剂与配体的摩尔比为1:2～1:4；
所述的氧化剂为过碳酸钠、双氧水、过二硫酸钾、高锰酸钾、二氧化锰、过氧化二叔丁基、氧气、空气。
2.根据权利要求1所述的制备方法，其特征在于，所述的无水有机溶剂为四氢呋喃、乙二醇二甲醚、二氯甲烷、乙醚、二甲基亚砜、四氯化碳、甲苯、N,N-二甲基甲酰胺、正己烷。
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