CN111205301B - 呋喃并[2,3-c]色烯衍生物及其制备方法 - Google Patents
呋喃并[2,3-c]色烯衍生物及其制备方法 Download PDFInfo
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Abstract
本发明涉及有机合成领域,公开了一种呋喃并[2,3‑c]色烯衍生物及其制备方法,所述制备方法包括:(1)将苯酚衍生物、1‑(2‑氧代‑2‑苯乙基)吡啶‑1‑溴化铵盐、有机胺催化剂和溶剂混合反应;(2)经TLC跟踪反应和硅胶色谱柱分离得到呋喃并[2,3‑c]色烯衍生物。解决了现有的方法反应时间较长,实验操作过程比较复杂,需要多步操作才能得到产物,且反应使用金属催化剂或添加剂量比较多的问题。
Description
技术领域
本发明涉及有机合成领域,具体地,涉及一种呋喃并[2,3-c]色烯衍生物及其制备方法。
背景技术
苯并吡喃有α-和γ-两个异构体。这两种化合物本身并不重要,但它们的某些衍生物却很重要。据文献报道,苯并呋喃类化合物具有抗组胺、选择性激活雌激素β受体和抗心律失常等多种生物活性。研究表明,2-芳酰基苯并呋喃类化合物对多种肿瘤细胞均有抑制作用,另外3-苯甲酰基-2H-1-苯并吡喃-2-酮衍生物对人乳腺癌细胞T47D和人急性早幼粒白血病细胞HL-60均有较强的抑制作用。
色烯类化合物是特殊的含氧类杂环化合物之一,不仅广泛存在于许多天然产物,而且具有广泛作用的生物活性化合物中的单位,诸如抗癌,利尿剂,抗凝剂和抗过敏活性,特别是杂环稠合苯并二氢吡喃与各种杂环的杂化物,如吡咯、呋喃、吡啶等,引起了人们的极大兴趣,由于其明显的结构复杂性和药用性,麦地卡宾,西卡宁,花青素和肿瘤生长抑制剂是天然的代表产品和合成的生物活性杂环稠合色烷。
传统合成呋喃并[2,3-c]色烯衍生物的方法有以下几种:(1)将(2-((二乙基氨基甲酰基)氧基)苯基)硼酸(8.05mmol),3-碘苯并呋喃(6.55mmol), Pd(PPh3)4(0.121mmol)和Na2CO3(10.0mL,2mol/L)在DME(100mL)中加热回流5h分离得到2-(苯并呋喃-2-基)苯基二乙基氨基甲酸酯中间产物,随后将此中间产物添加到含有LDA(3.05mmol)的THF(7mL)溶液中,并在0℃下搅拌30min,然后进行萃取所得的产物继续在乙酸中回流2h可分离得到6-H-苯并呋喃并[3,2-c]色烯类化合物。(2)以N-甲氧基苯甲酰胺(0.2mmol) 和2-重氮萘1-(2H)(0.1mmol)为原料加入催化剂[Cp*RhCl2]2(5mmol%),添加剂AgOAc(0.1mmol),甲苯为溶剂在85℃下反应18h即可分离得到5H- 二苯并呋喃[c,f]色烯类化合物。(3)采用2-杂芳基酚与CO的C-H羧化的方法, 2-(呋喃-3-基)苯酚(0.2mmol),CO2(1个大气压),Rh2(OAc)4(0.002mmol), PCy3(0.004mmol),t-BuOK(0.9mmol),二甘醇二甲醚作为溶剂在100℃下反应48h可分离得到4H-呋喃[2,3-c]色烯类化合物。(4)将间苯二酚(22.7 mmol),3-氧代-2,3-二氢苯并呋喃-2-羧酸乙酯(26.8mmol)溶于100mL无水苯中,加入2mL POCl3加热回至流9-10h。除去溶剂,减压下用水研磨残留物(3×50mL)。倒出水,使残留物重结晶进一步纯化可得到3-羟基苯并[4,5] 呋喃[2,3-c]色烯-6-酮类化合物。(5)此方法使用当量的苯甲酰基乙腈与2-芳基-3-硝基苯作为原料,加入1eq的Et3N,以乙醇作为溶剂在60℃下反应8 h可分离得到4H-呋喃[2,3-c]色烯类化合物。
综合以上几种方法发现现有方法合成4H-呋喃[2,3-c]色烯类化合物基本上反应时间较长,实验操作过程比较复杂,需要多步操作才能得到产物,且反应使用催化剂或添加剂量比较多。
因此,提供一种原料廉价易得、对环境友好、且反应条件温、产率高、副反应少的呋喃并[2,3-c]色烯衍生物及其制备方法是本发明亟需解决的问题。
发明内容
本发明的目的是提供一种呋喃并[2,3-c]色烯衍生物及其制备方法,解决了现有的方法反应时间较长,实验操作过程比较复杂,需要多步操作才能得到产物,且反应使用催化剂或添加剂量比较多的问题。
为了实现上述目的,本发明提供一种呋喃并[2,3-c]色烯衍生物的制备方法,所述制备方法包括:
(1)将苯酚衍生物、1-(2-氧代-2-苯乙基)吡啶-1-溴化铵盐、有机胺催化剂和溶剂混合反应;
(2)经TLC跟踪反应和硅胶色谱柱分离得到呋喃并[2,3-c]色烯衍生物。
本发明还提供了一种呋喃并[2,3-c]色烯衍生物,所述呋喃并[2,3-c]色烯衍生物由上述的制备方法制得。
通过上述技术方案,本发明提供了一种呋喃并[2,3-c]色烯衍生物及其制备方法,与现有合成方法相比,本发明以DMAP作为催化剂,以苯酚衍生物和1-(2-氧代-2-苯乙基)吡啶-1-溴化铵盐为原料,在溶剂和温和条件下反应即可高产率得到目标产物。该方法的改进较传统技术解决的关键技术有:(1) 以廉价易得、无毒、对环境友好的碱为催化剂;(2)使用价廉、易合成的化合物作为基本原料;(3)反应条件温和,反应过程中只需加入催化量的碱;(3)反应产物产率高,副反应少,反应后处理简单;(4)利用本方法可以高效合成得到一种4H-呋喃[2,3-c]色烯类化合物,产物结构复杂,易于进一步对产物结构进行修饰,便于合成得到具有潜在生物活性的4H-呋喃[2,3-c]色烯衍生物。
本发明的其它特征和优点将在随后的具体实施方式部分予以详细说明。
附图说明
附图是用来提供对本发明的进一步理解,并且构成说明书的一部分,与下面的具体实施方式一起用于解释本发明,但并不构成对本发明的限制。在附图中:
图1是化合物A1的核磁氢谱图;
图2是化合物A1的核磁碳谱图;
图3是化合物A2的核磁氢谱图;
图4是化合物A2的核磁碳谱图;
图5是化合物A3的核磁氢谱图;
图6是化合物A3的核磁碳谱图;
图7是化合物A4的核磁氢谱图;
图8是化合物A4的核磁碳谱图;
图9是化合物A5的核磁氢谱图;
图10是化合物A5的核磁碳谱图;
图11是化合物A6的核磁氢谱图;
图12是化合物A6的核磁碳谱图;
图13是化合物A7的核磁氢谱图;
图14是化合物A7的核磁碳谱图;
图15是化合物A8的核磁氢谱图;
图16是化合物A8的核磁碳谱图。
具体实施方式
以下对本发明的具体实施方式进行详细说明。应当理解的是,此处所描述的具体实施方式仅用于说明和解释本发明,并不用于限制本发明。
在本文中所披露的范围的端点和任何值都不限于该精确的范围或值,这些范围或值应当理解为包含接近这些范围或值的值。对于数值范围来说,各个范围的端点值之间、各个范围的端点值和单独的点值之间,以及单独的点值之间可以彼此组合而得到一个或多个新的数值范围,这些数值范围应被视为在本文中具体公开。
本发明提供了一种呋喃并[2,3-c]色烯衍生物的制备方法,所述制备方法包括:
(1)将苯酚衍生物、1-(2-氧代-2-苯乙基)吡啶-1-溴化铵盐、有机胺催化剂和溶剂混合反应;
(2)经TLC跟踪反应和硅胶色谱柱分离得到呋喃并[2,3-c]色烯衍生物。
在本发明的一种优选的实施方式中,苯酚衍生物选自2-(3-苯基-1-(吡咯烷基-1-基)丙-2-炔-1-基)苯酚、4-甲基-2-(3-苯基-1-(吡咯烷基-1-基)丙-2-炔-1- 基)苯酚、4-氯-2-(1-(吡咯烷-1-基)-3-(对甲苯基)丙-2-炔-1-基)苯酚、4-溴 -2-(1-(吡咯烷-1-基)-3-(对甲苯基)丙-2-炔-1-基)苯酚、2-(3-(4-甲氧基苯基)-1-(吡咯烷基-1-基)丙-2-炔-1-基)-4-甲基苯酚、4-氯-2-(3-(4-甲氧基苯基)-1-(吡咯烷-1-基)丙-2-炔-1-基)苯酚、3,5-二叔丁基-2-(1-(吡咯烷-1-基)-3-(对甲苯基)丙-2-炔-1-基)苯酚、2-溴-4-氯-6-(3-(4-甲氧基苯基)-1-(吡咯烷基-1-基) 丙-2-炔-1-基)苯酚、4-氯-2-(3-(3-硝基苯基)-1-(吡咯烷-1-基)丙-2-炔-1-基)苯酚、4-溴-2-(3-(环己-1-烯-1-基)-1-(吡咯烷-1-基)丙-2-炔-1-基)苯酚或4-溴 -2-(1-(吡咯烷-1-基)-3-(噻吩-3-基)丙-2-炔-1-基)苯酚中的一种。
在本发明的一种优选的实施方式中,溶剂选自乙腈、N,N-二甲基甲酰胺或二甲亚砜或四氢呋喃。
在本发明的一种优选的实施方式中,相对于5mL的溶剂,苯酚衍生物的用量为0.4-0.6mmol,1-(2-氧代-2-苯乙基)吡啶-1-溴化铵盐的用量为0.4-0.6 mmol,有机胺催化剂的用量为0.8-0.12mmol。
在本发明的一种优选的实施方式中,经TLC跟踪反应后,减压蒸去溶剂,之后硅胶色谱柱分离得到呋喃并[2,3-c]色烯衍生物。
在本发明的一种优选的实施方式中,在步骤(1)中,混合反应的条件包括:温度为75-100℃;和/或
时间为4-6h。
在本发明的一种优选的实施方式中,在硅胶色谱柱分离中,展开剂由正己烷和二氯甲烷组成。
在本发明的一种优选的实施方式中,展开剂由正己烷和二氯甲烷按照体积比为4-6:1的比例混合。
本发明还提供了一种呋喃并[2,3-c]色烯衍生物,所述呋喃并[2,3-c]色烯衍生物由上述的制备方法制得。
以下将通过实施例对本发明进行详细描述。
实施例1
向50mL反应瓶中依次加入2-(3-苯基-1-(吡咯烷基-1-基)丙-2-炔-1-基)苯酚(0.5mmol),1-(2-氧代-2-苯乙基)吡啶-1-溴化铵盐(0.5mmol),DMAP(0.1 mol),乙腈(5mL),80℃下反应5h,反应用薄层层析跟踪,反应结束后,减压蒸去溶剂,硅胶色谱柱分离(展开剂正己烷/二氯甲烷v:v=5:1),即可以 80%的产率得到纯的白色固体2,4-二苯基-4H-呋喃并[2,3-c]色烯A1。
2,4-Diphenyl-4H-furo[2,3-c]chromene(A1).Mp=120-121℃,1H NMR (500MHz,CDCl3)δ7.65(d,J=8.5Hz,2H),7.44(d,J=8.5Hz,2H),7.39-7.32 (m,6H),7.28-7.24(m,1H),7.11(t,J=8.5Hz,1H),6.98(t,J=7.5Hz,1H), 6.94(s,1H),6.93(d,J=7.5Hz,1H),6.55(s,1H);13C NMR(125MHz,CDCl3) δ155.2,151.1,146.4,138.7,130.2,128.8,128.7,127.8,127.7,127.2,123.8, 122.7,121.7,118.7,117.1,116.5,100.3,76.3;HRMS(APCI)m/z:calcd for C23H17O2[M+H]+325.1223,found 325.1225。
实施例2
向50mL反应瓶中依次加入4-甲基-2-(3-苯基-1-(吡咯烷基-1-基)丙-2-炔 -1-基)苯酚(0.5mmol),1-(2-氧代-2-苯乙基)吡啶-1-溴化铵盐(0.5mmol), DMAP(0.1mol),乙腈(5mL),80℃下反应5h,反应用薄层层析跟踪,反应结束后,减压蒸去溶剂,硅胶色谱柱分离(展开剂正己烷/二氯甲烷v:v=5:1),即可以72%的产率得到纯的白色固体8-甲基-2,4-二苯基-4H-呋喃并[2,3-c]色烯A2。
8-Methyl-2,4-diphenyl-4H-furo[2,3-c]chromene(A2).Mp=96-97℃,1H NMR(500MHz,CDCl3)δ7.64(d,J=8.5Hz,2H),7.43(d,J=8.5Hz,2H), 7.38-7.32(m,5H),7.27-7.25(m,1H),7.15(s,1H),6.93(s,1H),6.92(d,J=9.0 Hz,1H),6.84(d,J=8.5Hz,1H),6.50(s,1H),2.32(s,3H);13C NMR(125MHz, CDCl3)δ155.1,148.9,146.7,138.8,131.0,130.3,128.7,128.6,128.2,127.6, 127.1,123.7,123.3,118.4,117.2,116.3,100.3,76.1,20.7;HRMS(APCI)m/z: calcd for C24H19O2[M+H]+339.1379,found 339.1377。
实施例3
向50mL反应瓶中依次加入4-氯-2-(1-(吡咯烷-1-基)-3-(对甲苯基)丙-2- 炔-1-基)苯酚(0.5mmol),1-(2-氧代-2-苯乙基)吡啶-1-溴化铵盐(0.5mmol), DMAP(0.1mol),乙腈(5mL),80℃下反应5h,反应用薄层层析跟踪,反应结束后,减压蒸去溶剂,硅胶色谱柱分离(展开剂正己烷/二氯甲烷v:v=5:1),即可以84%的产率得到纯的白色固体8-氯-2-苯基-4-对甲苯基-4H-呋喃并 [2,3-c]色烯A3。
8-Clhloro-2-phenyl-4-(p-tolyl)-4H-furo[2,3-c]chromene(A3).Mp= 128-129℃,1H NMR(500MHz,CDCl3)δ7.64(d,J=8.5Hz,2H),7.37(t,J=8.0Hz,2H),7.30-7.26(m,5H),7.18(d,J=8.0Hz,2H),7.05(d,J=8.5Hz,1H), 6.90(s,1H),6.81(d,J=8.5Hz,1H),6.49(s,1H),2.34(s,3H);13C NMR(125 MHz,CDCl3)δ155.5,149.6,147.0,139.0,135.3,130.0,129.4,128.7,127.9, 127.2,126.5,123.8,122.5,120.3,117.8,116.5,100.1,76.3,21.2;HRMS(APCI) m/z:calcd for C24H18ClO2[M+H]+373.0989,found373.0990。
实施例4
向50mL反应瓶中依次加入4-溴-2-(1-(吡咯烷-1-基)-3-(对甲苯基)丙-2- 炔-1-基)苯酚(0.5mmol),1-(2-氧代-2-苯乙基)吡啶-1-溴化铵盐(0.5mmol), DMAP(0.1mol),乙腈(5mL),80℃下反应5h,反应用薄层层析跟踪,反应结束后,减压蒸去溶剂,硅胶色谱柱分离(展开剂正己烷/二氯甲烷v:v=5:1),即可以90%的产率得到纯的白色固体8-溴-2-苯基-4-对甲苯基-4H-呋喃并 [2,3-c]色烯A4。
8-Bromo-2-phenyl-4-(p-tolyl)-4H-furo[2,3-c]chromene(A4).Mp= 138-139℃,1H NMR(500MHz,CDCl3)δ7.64(d,J=8.0Hz,2H),7.44(s,1H), 7.38(t,J=7.5Hz,2H),7.29-7.27(m,3H),7.20-7.18(m,3H),6.90(s,1H),6.80 (d,J=8.5Hz,1H),6.50(s,1H),2.35(s,3H);13C NMR(125MHz,CDCl3)δ 155.5,150.2,147.0,139.0,135.1,130.3,130.0,129.5,128.8,127.2,125.4,124.0, 120.9,118.4,118.2,116.4,113.8,100.2,76.2,21.2;HRMS(APCI)m/z:calcd for C24H18BrO2[M+H]+419.0467,found 419.0464。
实施例5
向50mL反应瓶中依次加入2-(3-(4-甲氧基苯基)-1-(吡咯烷基-1-基)丙-2- 炔-1-基)-4-甲基苯酚(0.5mmol),1-(2-氧代-2-苯乙基)吡啶-1-溴化铵盐(0.5 mmol),DMAP(0.1mol),乙腈(5mL),80℃下反应5h,反应用薄层层析跟踪,反应结束后,减压蒸去溶剂,硅胶色谱柱分离(展开剂正己烷/二氯甲烷v:v=5:1),即可以69%的产率得到纯的白色固体4-(4-甲氧基苯基)-8-甲基 -2-苯基-4H-呋喃并[2,3-c]色烯A5。
4-(4-Methoxyphenyl)-8-methyl-2-phenyl-4H-furo[2,3-c]chromene(A5).Mp=109-110℃,1H NMR(500MHz,CDCl3)δ7.64(d,J=8.5Hz,2H),7.38-7.31 (m,4H),7.25(t,J=8.5Hz,1H),7.15(s,1H),6.94(s,1H),6.90-6.87(m,3H), 6.80(d,J=8.0Hz,1H),6.45(s,1H),3.78(s,3H),2.32(s,3H);13C NMR(125 MHz,CDCl3)δ160.0,155.0,148.9,146.9,130.9,130.3,128.8,128.7,128.2, 127.6,123.8,123.2,118.5,117.3,116.3,114.0,100.3,75.9,55.2,20.7;HRMS (APCI)m/z:calcd for C25H21O3[M+H]+369.1485,found369.1484。
实施例6
向50mL反应瓶中依次加入4-氯-2-(3-(4-甲氧基苯基)-1-(吡咯烷-1-基) 丙-2-炔-1-基)苯酚(0.5mmol),1-(2-氧代-2-苯乙基)吡啶-1-溴化铵盐(0.5 mmol),DMAP(0.1mol),乙腈(5mL),80℃下反应5h,反应用薄层层析跟踪,反应结束后,减压蒸去溶剂,硅胶色谱柱分离(展开剂正己烷/二氯甲烷v:v=5:1),即可以78%的产率得到纯的白色固体8-氯-4-(4-甲氧基苯基)-2- 苯基-4H-呋喃并[2,3-c]色烯A6。
8-Chloro-4-(4-methoxyphenyl)-2-phenyl-4H-furo[2,3-c]chromene(A6).Mp=158-159℃,1H NMR(500MHz,CDCl3)δ7.63(d,J=8.5Hz,2H),7.36(t,J =8.0Hz,2H),7.31-7.24(m,4H),7.04(d,J=8.5Hz,1H),6.89-6.87(m,3H), 6.82(d,J=9.0Hz,1H),6.47(s,1H),3.78(s,3H);13C NMR(125MHz,CDCl3) δ160.2,155.5,149.6,147.1,130.3,130.0,128.8,128.7,127.9,127.3,126.5, 123.8,122.5,120.3,117.8,116.6,114.1,100.1,76.1,55.2;HRMS(APCI)m/z: calcd for C24H18ClO3[M+H]+389.0939,found 389.0937。
实施例7
向50mL反应瓶中依次加入3,5-二叔丁基-2-(1-(吡咯烷-1-基)-3-(对甲苯基)丙-2-炔-1-基)苯酚(0.5mmol),1-(2-氧代-2-苯乙基)吡啶-1-溴化铵盐(0.5 mmol),DMAP(0.1mol),乙腈(5mL),80℃下反应5h,反应用薄层层析跟踪,反应结束后,减压蒸去溶剂,硅胶色谱柱分离(展开剂正己烷/二氯甲烷v:v=5:1),即可以78%的产率得到纯的黄色固体6,8-二叔丁基-2-苯基-4- 对甲苯基-4H-呋喃并[2,3-c]色烯A7。
6,8-Di-tert-butyl-2-phenyl-4-(p-tolyl)-4H-furo[2,3-c]chromene(A7).Mp= 98-99℃,1H NMR(500MHz,CDCl3)δ7.64(d,J=7.5Hz,2H),7.37-7.34(m, 4H),7.26(s,1H),7.24(t,J=7.5Hz,1H),7.20-7.19(m,3H),7.18(d,J=8.0Hz, 2H),7.00(s,1H),6.47(s,1H),2.37(s,3H),1.39(s,9H),1.32(s,9H);13C NMR (125MHz,CDCl3)δ154.8,147.2,146.6,143.5,138.8,137.2,135.2,130.5, 129.2,128.8,127.7,127.4,123.7,122.5,118.8,118.1,117.7,100.7,76.1,34.9, 34.4,31.6,29.9,21.3;HRMS(APCI)m/z:calcdfor C32H35O2[M+H]+ 451.2631,found 451.2636。
实施例8
向50mL反应瓶中依次加入2-溴-4-氯-6-(3-(4-甲氧基苯基)-1-(吡咯烷基-1-基)丙-2-炔-1-基)苯酚(0.5mmol),1-(2-氧代-2-苯乙基)吡啶-1-溴化铵盐 (0.5mmol),DMAP(0.1mol),乙腈(5mL),80℃下反应5h,反应用薄层层析跟踪,反应结束后,减压蒸去溶剂,硅胶色谱柱分离(展开剂正己烷/二氯甲烷v:v=5:1),即可以82%的产率得到纯的黄色固体6-溴-8-氯-4-(4-甲氧基苯基)-2-苯基-4H-呋喃并[2,3-c]色烯A8。
6-Bromo-8-chloro-4-(4-methoxyphenyl)-2-phenyl-4H-furo[2,3-c]chromene(A8).Mp=166-167℃,1H NMR(500MHz,CDCl3)δ7.66(d,J=8.5Hz,2H), 7.39(t,J=7.5Hz,2H),7.31-7.30(m,4H),7.23(s,1H),6.89(s,1H),6.88(s, 2H),6.61(s,1H),3.79(s,3H);13C NMR(125MHz,CDCl3)δ160.2,155.9, 147.4,146.5,130.4,130.0,129.8,128.8,128.4,128.1,126.9,123.9,121.7,121.4, 116.2,114.1,111.2,100.1,76.4,55.3;HRMS(APCI)m/z:calcd for C24H17BrClO3[M+H]+469.0023,found 469.0031。
实施例9
向50mL反应瓶中依次加入4-氯-2-(3-(3-硝基苯基)-1-(吡咯烷-1-基)丙 -2-炔-1-基)苯酚(0.5mmol),1-(2-氧代-2-苯乙基)吡啶-1-溴化铵盐(0.5 mmol),DMAP(0.1mol),乙腈(5mL),80℃下反应5h,反应用薄层层析跟踪,反应结束后,减压蒸去溶剂,硅胶色谱柱分离(展开剂正己烷/二氯甲烷v:v=5:1),即可以67%的产率得到纯的黄色固体8-氯-4-(3-硝基苯基)-2-苯基-4H-呋喃并[2,3-c]色烯A9。
8-Chloro-4-(3-nitrophenyl)-2-phenyl-4H-furo[2,3-c]chromene(A9).Mp=171-172℃,1H NMR(500MHz,CDCl3)δ8.33(s,1H),8.23(d,J=7.5Hz,1H), 7.75(d,J=8.0Hz,1H),7.64(d,J=8.5Hz,2H),7.57(t,J=8.0Hz,1H),7.39(t, J=8.0Hz,2H),7.32-7.29(m,2H),7.11(d,J=8.5Hz,1H),6.91(s,1H),6.89(d, J=8.5Hz,1H),6.63(s,1H);13CNMR(125MHz,CDCl3)δ156.2,149.1,148.5, 145.2,140.3,132.9,129.9,129.6,128.8,128.3,127.8,127.2,123.9,122.8,122.1, 119.9,117.8,116.9,100.2,75.1;HRMS(APCI)m/z:calcd for C23H15ClNO4[M +H]+404.0684,found 404.0681。
实施例10
向50mL反应瓶中依次加入4-溴-2-(3-(环己-1-烯-1-基)-1-(吡咯烷-1-基) 丙-2-炔-1-基)苯酚(0.5mmol),1-(2-氧代-2-苯乙基)吡啶-1-溴化铵盐(0.5 mmol),DMAP(0.1mol),乙腈(5mL),80℃下反应5h,反应用薄层层析跟踪,反应结束后,减压蒸去溶剂,硅胶色谱柱分离(展开剂正己烷/二氯甲烷v:v=5:1),即可以80%的产率得到纯的无色油状8-溴-4-(环己-1-烯-1-基)-2- 苯基-4H-呋喃并[2,3-c]色烯A10。
8-Bromo-4-(cyclohex-1-en-1-yl)-2-phenyl-4H-furo[2,3-c]chromene(A10).1H NMR(500MHz,CDCl3)δ7.69(d,J=7.0Hz,2H),7.38(s,1H),7.30(t,J= 7.5Hz,1H),7.20(d,J=8.5Hz,1H),6.84(s,1H),6.81(d,J=8.5Hz,3H),5.84 (s,1H),5.81-5.79(m,1H),2.13-2.09(m,3H),2.01-1.98(m,1H),1.65-1.55(m, 4H);13C NMR(125MHz,CDCl3)δ155.2,151.0,146.5,135.3,130.1,128.8, 128.0,127.8,125.3,123.8,120.8,117.8,116.6,113.4,100.1,79.2,25.1,24.0, 22.3,22.1;HRMS(APCI)m/z:calcd for C23H20BrO2[M+H]+409.0621,found 409.0623。
实施例11
向50mL反应瓶中依次加入4-溴-2-(1-(吡咯烷-1-基)-3-(噻吩-3-基)丙-2- 炔-1-基)苯酚(0.5mmol),1-(2-氧代-2-苯乙基)吡啶-1-溴化铵盐(0.5mmol), DMAP(0.1mol),乙腈(5mL),80℃下反应5h,反应用薄层层析跟踪,反应结束后,减压蒸去溶剂,硅胶色谱柱分离(展开剂正己烷/二氯甲烷v:v=5:1),即可以80%的产率得到纯的黄色固体8-溴-2-苯基-4-(噻吩-3-基)-4H-呋喃并 [2,3-c]色烯A11。
8-Bromo-2-phenyl-4-(thiophen-3-yl)-4H-furo[2,3-c]chromene(A11).Mp=123-124℃,1H NMR(500MHz,CDCl3)δ7.67(d,J=7.5Hz,2H),7.44(s,1H), 7.40(t,J=7.5Hz,2H),7.31-7.29(m,3H),7.21(d,J=8.5Hz,1H),7.13(d,J= 4.5Hz,1H),6.89(s,1H),6.82(d,J=8.5Hz,1H),6.59(s,1H);13C NMR(125 MHz,CDCl3)δ155.5,149.9,146.7,139.4,130.3,130.0,128.8,128.0,126.7, 126.2,125.4,124.0,123.9,120.9,118.4,116.2,114.1,100.2,71.9;HRMS(APCI) m/z:calcd for C21H14BrO2S[M+H]+410.9872,found410.9871。
以上详细描述了本发明的优选实施方式,但是,本发明并不限于上述实施方式中的具体细节,在本发明的技术构思范围内,可以对本发明的技术方案进行多种简单变型,这些简单变型均属于本发明的保护范围。
另外需要说明的是,在上述具体实施方式中所描述的各个具体技术特征,在不矛盾的情况下,可以通过任何合适的方式进行组合。
此外,本发明的各种不同的实施方式之间也可以进行任意组合,只要其不违背本发明的思想,其同样应当视为本发明所公开的内容。
Claims (5)
1.一种呋喃并[2,3-c]色烯衍生物的制备方法,其特征在于,所述制备方法包括:
(1)将苯酚衍生物、1-(2-氧代-2-苯乙基)吡啶-1-溴化铵盐、有机胺催化剂和溶剂混合反应;
(2)经TLC跟踪反应和硅胶色谱柱分离得到呋喃并[2,3-c]色烯衍生物;
其中,有机胺催化剂为DMAP;
苯酚衍生物选自2-(3-苯基-1-(吡咯烷基-1-基)丙-2-炔-1-基)苯酚、4-甲基-2-(3-苯基-1-(吡咯烷基-1-基)丙-2-炔-1-基)苯酚、4-氯-2-(1-(吡咯烷-1-基)-3-(对甲苯基)丙-2-炔-1-基)苯酚、4-溴-2-(1-(吡咯烷-1-基)-3-(对甲苯基)丙-2-炔-1-基)苯酚、2-(3-(4-甲氧基苯基)-1-(吡咯烷基-1-基)丙-2-炔-1-基)-4-甲基苯酚、4-氯-2-(3-(4-甲氧基苯基)-1-(吡咯烷-1-基)丙-2-炔-1-基)苯酚、3,5-二叔丁基-2-(1-(吡咯烷-1-基)-3-(对甲苯基)丙-2-炔-1-基)苯酚、2-溴-4-氯-6-(3-(4-甲氧基苯基)-1-(吡咯烷基-1-基)丙-2-炔-1-基)苯酚、4-氯-2-(3-(3-硝基苯基)-1-(吡咯烷-1-基)丙-2-炔-1-基)苯酚、4-溴-2-(3-(环己-1-烯-1-基)-1-(吡咯烷-1-基)丙-2-炔-1-基)苯酚或4-溴-2-(1-(吡咯烷-1-基)-3-(噻吩-3-基)丙-2-炔-1-基)苯酚中的一种;
相对于5 mL的溶剂,苯酚衍生物的用量为0.4-0.6 mmol,1-(2-氧代-2-苯乙基)吡啶-1-溴化铵盐的用量为0.4-0.6 mmol,有机胺催化剂的用量为0.8-0.12 mmol;
在步骤(1)中,混合反应的条件包括:温度为75-100 ℃,时间为4-6 h。
2.根据权利要求1所述的制备方法,其中,溶剂选自乙腈、N,N-二甲基甲酰胺或二甲亚砜或四氢呋喃。
3.根据权利要求1所述的制备方法,其中,经TLC跟踪反应后,减压蒸去溶剂,之后硅胶色谱柱分离得到呋喃并[2,3-c]色烯衍生物。
4.根据权利要求1所述的制备方法,其中,在硅胶色谱柱分离中,展开剂由正己烷和二氯甲烷组成。
5.根据权利要求4所述的制备方法,其中,展开剂由正己烷和二氯甲烷按照体积比为4-6:1的比例混合。
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