CN107973691B - 钌催化芳香酮与二苯乙炔环化反应制备多芳取代萘衍生物的方法及应用 - Google Patents

钌催化芳香酮与二苯乙炔环化反应制备多芳取代萘衍生物的方法及应用 Download PDF

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CN107973691B
CN107973691B CN201711327577.3A CN201711327577A CN107973691B CN 107973691 B CN107973691 B CN 107973691B CN 201711327577 A CN201711327577 A CN 201711327577A CN 107973691 B CN107973691 B CN 107973691B
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张殊佳
高杰
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Abstract

本发明涉及钌催化芳香酮与二苯乙炔环化反应制备多芳取代萘衍生物的方法及应用。本发明使用较廉价的钌作为催化剂，将芳香酮β‑H活化合成六元环即生成多芳取代萘衍生物；反应过程中无需添加剂及氧化剂，仅使用简单的碱，在温和反应条件下进行。本发明提供的合成方法简单易行、科学合理、绿色环保、经济实用，适合规模化生产。

Description

钌催化芳香酮与二苯乙炔环化反应制备多芳取代萘衍生物的 方法及应用
技术领域
本发明涉及医药技术及光电材料领域，主要涉及多芳取代萘衍生物的制备方法及应用。
背景技术
多芳取代萘衍生物由于其独特的电化学，光化学性能以及它们在n共轭的功能材料上的应用，使其在有机荧光材料、半导体材料等方面的应用越来越广泛，并且多芳取代萘衍生物在药物合成方面也有重要应用。现有技术中已采用的制备方法相比以前的环金属化、芳基卤、芳基酸等比较苛刻的条件有了很大的突破。目前，多采用在温和条件下通过过渡金属催化芳香苯环的C-H键(甚至双C-H键)活化与炔烃发生环化反应制备多芳取代的萘衍生物。但该方法存在缺陷，这些反应需要一定量的配体或者当量的金属盐做氧化剂才能完成催化循环，不仅提高了生产成本，而且金属盐多为对环境污染的重金属(铜、银等)盐类。基于此，本领域需要更加环保、绿色、经济的方法来合成多芳取代萘衍生物。
发明内容
为弥补现有技术的不足，本发明提供了一种无需添加剂及氧化剂在温和条件下以较廉价的钌([RuCl2(p-cymene)]2)作为催化剂合成了多芳取代萘的衍生物的方法。
本发明采用如下技术方案：多芳取代萘的衍生物，具有如通式Ⅰ所示的结构：
Figure BDA0001505966650000011
其中，R1与R2为相同的-CH3、-OCH3、-F、-CI、-Br或-I。
本发明另一个目的是请求保护上述多芳取代萘的衍生物的制备方法，即：将二苯乙炔与芳香酮作为原料，加入[RuCl2(p-cymene)]2、碱和非极性有机溶剂，在氮气环境下加热至80-100℃反应12-24h，经柱层析分离得到多芳取代萘的衍生物；所述的二苯乙炔与芳香酮摩尔比为1:2，[RuCl2(p-cymene)]2占二苯乙炔的15mol％，碱与芳香酮的摩尔比为1:1。
优选的，所述的芳香酮为：
Figure BDA0001505966650000012
其中R1与R2为相同的-CH3、-OCH3、-F、-CI、-Br或-I；
优选的，芳香酮为
Figure BDA0001505966650000021
Figure BDA0001505966650000022
Figure BDA0001505966650000023
的一种。
进一步的，所述非极性有机溶剂为苯、甲苯、二氯乙烷、氯仿、苯乙烯、环乙烷或己烷中任一种。优选甲苯。
进一步的，所述的碱为KOAc、Na2CO3、Cs2CO3、K2CO3、Li2CO3、NaOAc、LiOAc中的一种或一种以上。
作为本发明优选的实施方案，该多芳取代萘衍生物的制备方法为：将芳香酮和二苯乙炔置于封管中，加入[RuCl2(p-cymene)]2和甲苯，同时加入干燥的碳酸钠和醋酸钾在氮气环境下加热至100℃反应24小时，经柱层析分离得到多芳取代萘的衍生物。
本发明第三个目的是请求保护上述多芳取代萘的衍生物在药物制备及光电材料领域上的应用。
比如用于新型酪氨酸蛋白激酶抑制剂
Figure BDA0001505966650000024
或蓝光材料
Figure BDA0001505966650000025
的制备。
与现有技术相比，本发明的有益效果是：
本发明使用较廉价的钌([RuCl2(p-cymene)]2)作为催化剂，将芳香酮β-H活化合成六元环即生成多芳取代萘衍生物；反应过程中无需添加剂及氧化剂，仅使用简单的碱，在温和反应条件下进行。本发明提供的合成方法简单易行、科学合理、绿色环保、经济实用，适合规模化生产。
具体实施方式
下面通过具体实施例详述本发明，但不限制本发明的保护范围。如无特殊说明，本发明所采用的实验方法均为常规方法，所用实验器材、材料、试剂等均可从化学公司购买。
实施例1
Figure BDA0001505966650000031
向带有磁子的25mL封管中加入二苯乙炔(18mg，0.1mmol)，相应的芳香酮(0.2mmol)，催化剂[RuCl2(p-cymene)]2(9mg，15％mol)，0.5mL甲苯，之后加入干燥的碳酸钠(21mg，0.2mmol)和醋酸钾(19mg，0.2mmol)，抽换氮气三次，100℃下反应24小时，然后经柱色谱分离(洗脱剂为：石油醚)从而得到目标化合物。表征如下。
7-甲基-3-(4-甲基苄基)-1,2-二苯基萘：收率：58％，熔点：124-125℃。1H NMR(CDCl3,400MHz)δ7.71(d,J＝8.0Hz,1H),7.61(s,1H),7.28(dd,J1＝1.2Hz；J2＝8.4Hz,1H),7.14-7.23(m,4H),7.05-7.10(m,5H),7.00(d,J＝8.0Hz,2H),6.90-6.93(m,2H),6.85(d,J＝7.6Hz,2H),3.86(s,2H),2.35(s,3H),2.29(s,3H).13C NMR(CDCl3,100MHz)δ140.2,139.9,139.6,138.4,137.9,136.7,135.2,135.2,131.6,131.1,130.5,129.1,128.8,128.0,127.6,127.4,127.4,127.3,126.2,126.1,125.6,40.0,22.0,21.1.HRMS(EI-TOF)calcd for C31H26(M+):398.2035,found:398.2037.
实施例2
Figure BDA0001505966650000032
向带有磁子的25mL封管中加入二苯乙炔(18mg，0.1mmol)，相应的芳香酮(0.2mmol)，催化剂[RuCl2(p-cymene)]2(9mg，15％mol)，0.5mL甲苯，之后加入干燥的碳酸钠(21mg，0.2mmol)和醋酸钾(19mg，0.2mmol)，抽换氮气三次，100℃下反应24小时，然后经柱色谱分离(洗脱剂为：石油醚)从而得到目标化合物。表征如下。
7-甲氧基-3-(4-甲氧基苄基)-1,2-二苯基萘：收率：45％，熔点：137-139℃。1HNMR(CDCl3,400MHz)δ7.72(d,J＝8.8Hz,1H),7.59(s,1H),7.16-7.18(m,2H),7.07-7.14(m,7H),6.90-6.92(m,2H),6.86(d,J＝8.8Hz,2H),6.76(d,J＝2.8Hz,1H),6.72-6.74(m,2H),3.83(s,2H),3.76(s,3H),3.64(s,3H).13C NMR(CDCl3,100MHz)δ157.7,157.4,140.2,139.6,138.1,135.5,133.2,132.5,130.9,130.4,130.1,129.1,128.4,127.5,127.3,126.3,126.1,118.2,113.5,105.4,55.3,55.1,39.5.HRMS(EI-TOF)calcd for C31H26O2(M+):430.1933,found:430.1937.
实施例3
Figure BDA0001505966650000041
向带有磁子的25mL封管中加入二苯乙炔(18mg，0.1mmol)，相应的芳香酮(0.2mmol)，催化剂[RuCl2(p-cymene)]2(9mg，15％mol)，0.5mL甲苯，之后加入干燥的碳酸钠(21mg，0.2mmol)和醋酸钾(19mg，0.2mmol)，抽换氮气三次，100℃下反应24小时，然后经柱色谱分离(洗脱剂为：石油醚)从而得到目标化合物。表征如下。
7-氟-3-(4-氟苄基)-1,2-二苯基萘：收率：60％，熔点：107-108℃。1H NMR(CDCl3,400MHz)δ7.81(dd,J1＝5.6Hz；J2＝9.2Hz,1H),7.65(s,1H),7.15-7.25(m,4H),7.04-7.10(m,6H),6.85-6.88(m,6H),3.89(s,2H).13C NMR(CDCl3,100MHz)δ162.5,161.9,160.1,159.5,140.6,139.6,138.9(d,JC-F＝5.6Hz),138.8,136.6(d,JC-F＝3.3Hz),136.3(d,JC-F＝4.3Hz),132.5(d,JC-F＝7.6Hz),130.8,130.4(d,JC-F＝7.2Hz),130.3,129.9,129.8,127.7(d,JC-F＝6.4Hz),127.4,126.7,126.4,116.4,116.1,115.0,114.8,110.4,110.2,39.8.HRMS(EI-TOF)calcd for C29H20F2(M+):406.1533,found:406.1529.
实施例4
Figure BDA0001505966650000042
向带有磁子的25mL封管中加入二苯乙炔(18mg，0.1mmol)，相应的芳香酮(0.2mmol)，催化剂[RuCl2(p-cymene)]2(9mg，15％mol)，0.5mL甲苯，之后加入干燥的碳酸钠(21mg，0.2mmol)和醋酸钾(19mg，0.2mmol)，抽换氮气三次，100℃下反应24小时，然后经柱色谱分离(洗脱剂为：石油醚)从而得到目标化合物。表征如下。
7-氯-3-(4-氯苄基)-1,2-二苯基萘：产率：55％。熔点：130-131℃。1H NMR(CDCl3,400MHz)δ7.77(d,J＝8.8Hz,1H),7.63(s,1H),7.44(s,1H),7.39-7.42(m,1H),7.03-7.20(m,10H),6.82-6.87(m,4H),3.88(s,2H).13C NMR(CDCl3,100MHz)δ140.7,139.4,139.0,138.7,138.4,137.4,132.4,131.7,131.0,130.8,130.4,130.2,129.1,128.3,127.7,127.6,127.5,126.8,126.7,126.4,125.7,40.0.HRMS(EI-TOF)calcd for C29H20Cl2(M+):438.0942,found:438.0939.
实施例5
Figure BDA0001505966650000051
向带有磁子的25mL封管中加入二苯乙炔(18mg，0.1mmol)，相应的芳香酮(0.2mmol)，催化剂[RuCl2(p-cymene)]2(9mg，15％mol)，0.5mL甲苯，之后加入干燥的碳酸钠(21mg，0.2mmol)和醋酸钾(19mg，0.2mmol)，抽换氮气三次，100℃下反应24小时，然后经柱色谱分离(洗脱剂为：石油醚)从而得到目标化合物。表征如下。
7-溴-3-(4-溴苄基)-1,2-二苯基萘：收率：64％，熔点：136-138℃。1H NMR(CDCl3,400MHz)δ7.69(d,J＝9.2Hz,1H),7.61-7.62(m,2H),7.53(dd,J1＝1.6Hz；J2＝8.8Hz,1H),7.27-7.29(m,2H),7.16-7.19(m,3H),7.08-7.09(m,3H),7.03-7.05(m,2H),6.84-6.86(m,2H),6.77(d,J＝8.4Hz,2H),3.85(s,2H).13C NMR(CDCl3,100MHz)δ140.7,139.5,139.4,138.7,138.4,137.5,132.8,131.2,130.9,130.8,130.2,129.4,129.2,128.9,127.8,127.7,127.5,126.8,126.5,120.1,119.8,40.1.HRMS(EI-TOF)calcd for C29H20Br2(M+):525.9932,found:525.9935.
实施例6
Figure BDA0001505966650000052
向带有磁子的25mL封管中加入二苯乙炔(18mg，0.1mmol)，相应的芳香酮(0.2mmol)，催化剂[RuCl2(p-cymene)]2(9mg，15％mol)，0.5mL甲苯，之后加入干燥的碳酸钠(21mg，0.2mmol)和醋酸钾(19mg，0.2mmol)，抽换氮气三次，100℃下反应24小时，然后经柱色谱分离(洗脱剂为：石油醚)从而得到目标化合物。表征如下。
7-碘-3-(4-碘苄基)-1,2-二苯基萘：收率：68％，熔点：139-141℃。1H NMR(CDCl3,400MHz)δ7.83(d,J＝0.8Hz,1H),7.71(dd,J1＝1.6Hz；J2＝8.4Hz,1H),7.59(s,1H),7.55(d,J＝8.8Hz,1H),7.48(dd,J1＝1.6Hz；J2＝6.8Hz,2H),7.15-7.19(m,3H),7.07-7.09(m,3H),7.02-7.04(m,2H),6.83-6.86(m,2H),6.65(d,J＝8.0Hz,2H),3.84(s,2H).13C NMR(CDCl3,100MHz)δ140.5,140.2,139.4,138.4,138.3,137.6,137.2,135.5,134.6,133.3,131.5,131.2,130.9,130.3,129.1,127.8,127.6,127.5,126.8,126.5,91.8,91.2,40.2.HRMS(EI-TOF)calcd for C29H20I2(M+):621.9654,found:621.9656.
对比例：
向带有磁子的25mL封管中加入二苯乙炔0.1mmol，芳香酮
Figure BDA0001505966650000061
(0.2mmol)，催化剂[RuCl2(p-cymene)]20.01mol，之后加入0.5mL有机溶剂和与芳香酮等摩尔的干燥的碱，抽换氮气三次，100℃下反应24小时，然后经柱色谱分离(洗脱剂为：石油醚)从而得到目标化合物
Figure BDA0001505966650000062
计算产率，结果如表1所示。
表1
Figure BDA0001505966650000063
Figure BDA0001505966650000071
*催化剂为0.015mmol时的产率
由表1数据和对实施例1-6产率对比可知，当有机溶剂选择甲苯，碱为碳酸钠和醋酸钾时，催化剂用量为15mol％时，产率最高。故而，在实验过程中均采用此最佳反应条件进行。
以上所述，仅为本发明创造较佳的具体实施方式，但本发明创造的保护范围并不局限于此，任何熟悉本技术领域的技术人员在本发明创造披露的技术范围内，根据本发明创造的技术方案及其发明构思加以等同替换或改变，都应涵盖在本发明创造的保护范围之内。

Claims (2)

1.一种多芳取代萘衍生物的制备方法，其特征在于，将芳香酮和二苯乙炔置于封管中，加入[RuCl2(p-cymene)]2和甲苯，同时加入干燥的碳酸钠和醋酸钾在氮气环境下加热至100℃反应24小时，经柱层析分离得到通式Ⅰ所示的结构多芳取代萘衍生物；
Figure FDA0002436556110000011
所述的二苯乙炔与芳香酮摩尔比为1:2，[RuCl2(p-cymene)]2占二苯乙炔的15mol％，碱与芳香酮的摩尔比为1:1
所述的芳香酮为：
Figure FDA0002436556110000012
其中R1与R2为相同的-CH3、-OCH3、-F、-Cl、-Br或-I。
2.根据权利要求1所述的方法，其特征在于，芳香酮为
Figure FDA0002436556110000013
Figure FDA0002436556110000014
Figure FDA0002436556110000015
中的一种。
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