CN109705070B - 一种5,5’-二烷氧酰基-[2,2’]联呋喃类化合物的制备方法 - Google Patents
一种5,5’-二烷氧酰基-[2,2’]联呋喃类化合物的制备方法 Download PDFInfo
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Abstract
本发明公开了一种5,5’‑二烷氧酰基‑[2,2’]联呋喃类化合物的制备方法,属于联呋喃类化合物的制备领域。本发明的制备方法将
Description
技术领域
本发明属于高性能聚醋、环氧树脂、聚酞胺和聚氨醋等聚合物单体制备领域,具体涉及一种5,5’-二烷氧酰基-[2,2’]联呋喃类化合物制备方法。
背景技术
随着人们对化石资源的过渡开采,有限的化石资源日益变得枯竭,另外,化石资源炼制过程中带来大量的环境污染和温室效应,因此利用具有生物质来源的平台化合物制备各种官能材料受到各国政府以及学术界的高度重视并投入大量人力物力进行研究。比如呋喃二甲酸因含有刚性的呋喃环和对位的二甲酸基结构,可直接用于聚醋、环氧树脂、聚酞胺、聚氨醋等高性能工程塑料。比如现在利用聚呋喃二甲酸替代传统的对苯二甲酸酯类(PET),其在模量、抗蠕变等方面具有优良的力学性能,同时具有更高的玻璃化转变温度和热变形温度。但是聚呋喃二甲酸再热稳定性上尚有欠缺。最近芬兰科学家JuhaP.Heiskanen(Macromolecules 2018,51,1822-1829)报道联5,5’-二烷氧酰基-[2,2’]联呋喃聚酯的热稳定性较聚呋喃二甲酸具有明显提高。
目前对于联5,5’-二烷氧酰基-[2,2’]联呋喃聚酯单体的合成主要包括以下三种方法,方法一是基于钯催化条件下由2-糠酸甲酯氧化偶联得到,该方法是高压气相反应,温度高,产物中等(Jpn.Kokai Tokkyo Koho,2018150415;Organic Letters,16(10),2732-2735;2014)。方法二是基于钯催化下2-糠酸甲酯和5-溴-2-糠酸甲酯发生中性偶联反应得到,该反应需要在强碱性条件下进行,产率比较低(Macromolecules,51(5),1822-1829;2018)。第三种方法是基于5-溴-2-呋喃糠酸甲酯在NiCl2(PPh3)2催化剂下还原偶联得到,但是该方法需要一当量的金属单质如锌,铟等作为还原剂,不原子经济,成本高(TetrahedronLetters,49(27),4302-4305;2008;Jpn.Kokai Tokkyo Koho,2018150415)。另外使用的Ni催化剂具有环境危害性。以上三种方法的合成路线如下所示:
发明内容
为了克服现有的联5,5’-二烷氧酰基-[2,2’]联呋喃酯合成技术中的缺点与不足,本发明的目的在于提供一种联5,5’-二烷氧酰基-[2,2’]联呋喃酯化合物的制备方法。该方法不需要严格无水条件,不需要使用强碱,不需要高压条件,用廉价的还原剂替代金属锌单质作为还原剂,具有操作简便成本低廉等优势。
本发明的目的通过下述技术方案实现。
一种5,5’-二烷氧酰基-[2,2’]联呋喃类化合物的制备方法,其特征在于,包括如下步骤:
其中X=Cl,Br或I;R为C1~C17的饱和脂肪烃、脂环烃、苯基烷基。
优选的,所述5,5’-二烷氧酰基-[2,2’]联呋喃类化合物的结构如下所示:
优选的,所述回流反应的温度为0~160℃。
优选的,所述回流反应的时间为1~60小时。
优选的,所述有机溶剂为苯、甲苯、二甲苯、均三甲苯、氯苯、邻二氯苯、间二氯苯、对二氯苯、氟苯、五氟苯、六氟苯、乙酸乙酯、乙酸叔丁酯、乙酸丙酯、乙腈、苯腈、四氢呋喃、乙醚和1,4-二氧六环中的一种或几种的混合物。
优选的,所述的还原剂为甲醇、乙醇、异丙醇、丁醇,乙二醇,1,3-丙二醇,1,2-丙二醇,丙三醇,1,4丁二醇,葡萄糖和甘露糖中的一种或几种的混合物。
优选的,所述的催化剂为Fe(OAc)2、Cu(OAc)2、Co(OAc)2、Mn(OAc)2、Pd(OAc)2、Pd(PPh3)4、PdCl2、PdCl2(PPh3)2、PdCl2(PPh3)2、Pd2(dba)3、Ni(acac)2、Fe(acac)2、Fe(OTf)2、FeCl2、Fe(acac)3、Fe(OTf)3、FeCl3和FeCl2中的一种或几种的混合物。
优选的,所述稳定剂为聚乙烯吡咯烷酮(缩写PVP,分子量为1~6万)。
优选的,所述的碱为醋酸钾、醋酸钠、醋酸铯、碳酸钾、碳酸钠、碳酸氢钾、碳酸氢钠、氢氧化钠、氢氧化钾、磷酸钠、磷酸钾、磷酸氢钠、磷酸氢钾,三乙胺、吡啶、二异丙基乙基胺和N-甲基吗啡啉的一种或者几种的混合物。
本发明相对于现有技术,具有如下的优点与效果:
(1)本发明所用的还原剂是廉价可再生的醇类物质,不需要金属单质;
(2)本发明不需要严格的无水条件和高温高压操作,操作简单,成本低廉。
具体实施方式
下面结合实施例对本发明作进一步详细的描述,但本发明的实施方式不限于此。
实施例1
在25mL schlenk反应管中加入0.015mmol PdCl2(PPh3)2,55.9mgPVP(K30),0.75mmol乙酸钾,氮气条件下,加入2.5ml甲苯,再加入1mmol的乙醇和0.5mmol的110℃下回流反应30小时,减压脱除溶剂得粗产品,然后用快速柱层析分离得产物51mg(74%)。产物的结构表征物理常数:1H NMR(400MHz,CDCl3)δ7.25(d,J=3.6Hz,1H),6.91(d,J=3.6Hz,1H),4.40(q,J=7.1Hz,2H),1.41(t,J=7.1Hz,3H).13C NMR(100MHz,CDCl3)δ158.5,148.2,144.7,119.4,109.3,61.2,14.3.
实施例2
在100mL schlenk反应管中加入0.06mmol PdCl2(PPh3)2,224mgPVP(K30),3mmol乙酸钾,氮气条件下,加入10ml甲苯,再加入4mmol的异丙醇和2mmol的110℃下回流反应30小时,减压脱除溶剂得粗产品,然后用快速柱层析分离得产物220mg(71%)。产物的结构表征物理常数:1H NMR(400MHz,CDCl3)δ7.21(s,2H),6.88(s,2H),5.30–5.17(m,2H),1.37(d,J=5.8Hz,12H).13C NMR(100MHz,CDCl3)δ158.1,148.2,144.9,119.2,109.2,69.0,21.9.
实施例3
在50mL schlenk反应管中加入0.03mmol PdCl2(PPh3)2,112mgPVP(K30),1.5mmol乙酸钾,氮气条件下,加入5ml甲苯,再加入2mmol的正丁醇和1mmol的110℃下回流反应30小时,减压脱除溶剂得粗产品,然后用快速柱层析分离得产物102mg(61%)。产物的结构表征物理常数:1H NMR(400MHz,CDCl3)δ7.25(d,J=3.5Hz,1H),6.91(d,J=3.5Hz,1H),4.35(t,J=6.7Hz,2H),1.81–1.72(m,2H),1.49(d,J=7.5Hz,2H),1.00(t,J=7.5Hz,3H).13C NMR(100MHz,CDCl3)δ158.5,148.2,144.7,119.3,109.3,65.0,30.7,19.1,13.7.
实施例4
在25mL schlenk反应管中加入0.015mmol PdCl2(PPh3)2,55.9mgPVP(K30),0.75mmol乙酸钾,氮气条件下,加入2.5ml甲苯,再加入1mmol的异丁醇和0.5mmol的90℃下回流反应30小时,减压脱除溶剂得粗产品,然后用快速柱层析分离得产物104mg(62%)。产物的结构表征物理常数:1H NMR(400MHz,CDCl3)δ7.24(d,J=2.8Hz,2H),6.89(d,J=2.8Hz,2H),4.11(d,J=6.6Hz,4H),2.12–2.01(m,2H),1.01(d,J=6.7Hz,12H).13C NMR(100MHz,CDCl3)δ158.5,148.3,144.6,119.4,109.3,71.1,27.9,19.1.
实施例5
在25mL schlenk反应管中加入0.015mmol PdCl2(PPh3)2,55.9mgPVP(K30),0.75mmol乙酸钾,氮气条件下,加入2.5ml甲苯,再加入1mmol的乙醇和0.5mmol的60℃下回流反应30小时,减压脱除溶剂得粗产品,然后用快速柱层析分离得产物60mg(36%)。产物的结构表征物理常数:1H NMR(400MHz,CDCl3)δ7.12(d,J=3.5Hz,2H),6.83(d,J=3.5Hz,2H),1.59(s,18H).13C NMR(100MHz,CDCl3)δ157.8,148.0,145.6,118.7,108.9,82.3,28.2.
实施例6
在50mL schlenk反应管中加入0.03mmol PdCl2(PPh3)2,112mgPVP(K30),1.5mmol乙酸钾,氮气条件下,加入5ml甲苯,再加入2mmol的环丁醇和1mmol的25℃下回流反应30小时,减压脱除溶剂得粗产品,然后用快速柱层析分离得产物86mg(52%)。产物的结构表征物理常数:1H NMR(400MHz,CDCl3)δ7.23(d,J=3.5Hz,2H),6.88(d,J=3.5Hz,2H),5.29–5.13(m,2H),2.45(dt,J=15.0,7.5Hz,4H),2.22(dd,J=14.1,6.0Hz,4H),1.93–1.63(m,4H).13C NMR(100MHz,CDCl3)δ157.8,148.2,144.6,119.4,109.3,69.6,30.4,13.5.
实施例7
在100mL schlenk反应管中加入0.06mmol PdCl2(PPh3)2,224mgPVP(K30),3mmol乙酸钾,氮气条件下,加入10ml甲苯,再加入4mmol的环戊醇和2mmol的80℃下回流反应30小时,减压脱除溶剂得粗产品,然后用快速柱层析分离得产物228mg(64%)。产物的结构表征物理常数:1H NMR(400MHz,CDCl3)δ7.19(s,2H),6.87(s,2H),5.40(s,2H),1.96(s,4H),1.83(d,J=12.6Hz,8H),1.65(s,4H).13C NMR(100MHz,CDCl3)δ158.3,148.2,144.9,119.2,109.2,78.1,32.7,23.8.
实施例8
在100mL schlenk反应管中加入0.06mmol PdCl2(PPh3)2,224mgPVP(K30),1.5mmol乙酸钾,氮气条件下,加入10ml甲苯,再加入4mmol的正己醇和2mmol的120℃下反应30小时,减压脱除溶剂得粗产品,然后用快速柱层析分离得产物256mg(66%)。产物的结构表征物理常数:1H NMR(400MHz,CDCl3)δ7.23(d,J=3.6Hz,1H),6.89(d,J=3.6Hz,1H),4.32(t,J=6.8Hz,2H),1.80–1.71(m,2H),1.47–1.31(m,6H),0.91(t,J=7.0Hz,3H).13C NMR(100MHz,CDCl3)δ158.5,148.2,144.6,119.3,109.2,65.3,31.4,28.6,25.5,22.5,13.9.
实施例9
在25mL schlenk反应管中加入0.015mmol PdCl2(PPh3)2,55.9mgPVP(K30),50mmol乙酸钾,氮气条件下,加入2.5ml甲苯,再加入1mmol的环己醇和0.5mmol的110℃下回流反应30小时,减压脱除溶剂得粗产品,然后用快速柱层析分离得产物67mg(68%)。产物的结构表征物理常数:1H NMR(400MHz,CDCl3)δ7.21(d,J=2.2Hz,2H),6.88(d,J=2.5Hz,2H),5.01(dd,J=10.7,7.0Hz,2H),1.95(d,J=10.5Hz,4H),1.78(s,4H),1.63–1.25(m,12H).13C NMR(100MHz,CDCl3)δ158.0,148.2,145.0,119.1,109.2,73.7,31.6,25.4,23.7.
实施例10
在25mL schlenk反应管中加入0.015mmol PdCl2(PPh3)2,55.9mgPVP(K30),12.5mmol乙酸钾,氮气条件下,加入2.5ml甲苯,再加入1mmol的环庚醇和0.5mmol的110℃下回流反应30小时,减压脱除溶剂得粗产品,然后用快速柱层析分离得产物67mg(57%)。产物的结构表征物理常数:1H NMR(400MHz,CDCl3)δ7.20(d,J=3.6Hz,2H),6.88(d,J=3.6Hz,2H),5.23–5.13(m,2H),2.05–1.96(m,4H),1.86–1.67(m,8H),1.63–1.47(m,13H).13C NMR(100MHz,CDCl3)δ158.0,148.2,145.0,119.1,109.2,76.2,33.8,28.3,22.9.
实施例11
在100mL schlenk反应管中加入0.06mmol PdCl2(PPh3)2,224mgPVP(K30),100mmol乙酸钾,氮气条件下,加入2.5ml甲苯,再加入4mmol的正辛醇和2mmol的160℃下回流反应30小时,减压脱除溶剂得粗产品,然后用快速柱层析分离得产物74mg(66%)。产物的结构表征物理常数:1H NMR(400MHz,CDCl3)δ7.24(s,2H),6.91(s,2H),4.33(s,4H),1.77(s,4H),1.36(d,J=48.5Hz,21H),0.90(s,6H).13C NMR(101MHz,CDCl3)δ158.5,148.2,144.6,119.4,109.3,65.4,31.8,29.2,28.7,25.9,22.6,14.1.
实施例12
在100mL schlenk反应管中加入0.06mmol PdCl2(PPh3)2,224mgPVP(K30),2mmol乙酸钾,氮气条件下,加入2.5ml甲苯,再加入4mmol的异辛醇和2mmol的100℃下回流反应30小时,减压脱除溶剂得粗产品,然后用快速柱层析分离得产物77mg(70%)。产物的结构表征物理常数:1H NMR(400MHz,CDCl3)δ7.22(d,J=3.5Hz,2H),6.89(d,J=3.5Hz,2H),4.24(d,J=5.6Hz,4H),1.71(dd,J=11.6,5.7Hz,2H),1.48–1.28(m,16H),0.94(m,12H).13C NMR(100MHz,CDCl3)δ158.6,148.2,144.6,119.2,109.2,67.5,38.9,30.5,28.9,23.9,22.9,14.0,11.0.
实施例13
在25mL schlenk反应管中加入0.015mmol PdCl2(PPh3)2,55.9mgPVP(K30),0.75mmol乙酸钾,氮气条件下,加入2.5ml甲苯,再加入1mmol的仲辛醇和0.5mmol的110℃下回流反应30小时,减压脱除溶剂得粗产品,然后用快速柱层析分离得产物73mg(65%)。产物的结构表征物理常数:1H NMR(400MHz,CDCl3)δ7.20(d,J=3.6Hz,2H),6.88(d,J=3.6Hz,2H),5.14(dd,J=12.8,6.3Hz,2H),1.72(m,2H),1.65–1.54(m,2H),1.38–1.26(m,23H),0.88(t,J=6.7Hz,6H).13C NMR(100MHz,CDCl3)δ158.2,148.2,144.9,119.1,109.2,72.3,36.0,31.7,29.1,25.3,22.6,20.0,14.0.
实施例14
在25mL schlenk反应管中加入0.015mmol PdCl2(PPh3)2,55.9mgPVP(K30),0.75mmol乙酸钾,氮气条件下,加入2.5ml甲苯,再加入1mmol的环乙烷乙醇和0.5mmol的110℃下回流反应30小时,减压脱除溶剂得粗产品,然后用快速柱层析分离得产物78mg(70%)。产物的结构表征物理常数:1H NMR(400MHz,CDCl3)δ7.22(d,J=3.6Hz,2H),6.88(d,J=3.6Hz,2H),4.36(t,J=6.9Hz,4H),1.78(s,2H),1.77–1.69(m,6H),1.64(dd,J=13.5,6.6Hz,6H),1.43(dtd,J=14.3,7.3,3.6Hz,2H),1.29–1.13(m,6H),0.99(m,4H).13C NMR(101MHz,CDCl3)δ158.53,148.23,144.69,119.33,109.27,63.58,36.02,34.68,33.19,26.46,26.19.
实施例15
在25mL schlenk反应管中加入0.015mmol PdCl2(PPh3)2,55.9mgPVP(K30),1.6mmol乙酸钾,氮气条件下,加入2.5ml甲苯,再加入1mmol的L-薄荷醇和0.5mmol的110℃下回流反应30小时,减压脱除溶剂得粗产品,然后用快速柱层析分离得产物67mg(53%)。产物的结构表征物理常数:1H NMR(400MHz,CDCl3)δ7.21(d,J=3.4Hz,2H),6.89(d,J=3.4Hz,2H),4.93(td,J=10.8,4.1Hz,2H),2.11(d,J=11.9Hz,2H),1.98–1.88(m,2H),1.72(d,J=11.4Hz,4H),1.53(t,J=11.2Hz,4H),1.27(d,J=9.9Hz,2H),1.13(q,J=11.9Hz,4H),0.95–0.90(m,12H),0.82(d,J=6.9Hz,6H)13CNMR(100MHz,CDCl3)δ158.1,148.2,144.8,119.1,109.2,75.3,47.1,40.9,34.2,31.4,26.5,23.7,22.0,20.6,16.6.
实施例17
在25mL schlenk反应管中加入0.015mmol PdCl2(PPh3)2,55.9mgPVP(K30),0.75mmol乙酸钾,氮气条件下,加入2.5ml甲苯,再加入1mmol的苄醇和0.5mmol的100℃下回流反应30小时,减压脱除溶剂得粗产品,然后用快速柱层析分离得产物75mg(75%)。产物的结构表征物理常数:1H NMR(400MHz,CDCl3)δ7.38(dt,J=17.0,7.8Hz,10H),7.24(d,J=2.6Hz,2H),6.86(d,J=2.6Hz,2H),5.34(s,4H).13C NMR(100MHz,CDCl3)δ158.2,148.4,144.4,135.6,128.7,128.5,128.4,119.9,109.5,66.8.
实施例18
在50mL schlenk反应管中加入0.03mmol PdCl2(PPh3)2,112mgPVP(K30),30mmol乙酸钾,氮气条件下,加入5ml甲苯,再加入2mmol的苯基丙醇和1mmol的110℃下回流反应30小时,减压脱除溶剂得粗产品,然后用快速柱层析分离得产物61mg(54%)。产物的结构表征物理常数:1H NMR(400MHz,CDCl3)δ7.29(t,J=7.6Hz,4H),7.24–7.17(m,8H),6.90(d,J=3.6Hz,2H),4.35(t,J=6.5Hz,4H),2.77(t,J=7.6Hz,4H),2.16–1.99(m,5H).13C NMR(101MHz,CDCl3)δ158.4,148.3,144.5,141.0,128.5,128.4,126.1,119.5,109.4,64.5,32.2,30.2.
上述实施例为本发明较佳的实施方式,但本发明的实施方式并不受上述实施例的限制,其他的任何未背离本发明的精神实质与原理下所作的改变、修饰、替代、组合、简化,均应为等效的置换方式,都包含在本发明的保护范围之内。
Claims (6)
1.一种5,5’-二烷氧酰基-[2,2’]联呋喃类化合物的制备方法,其特征在于,包括如下步骤:
其中X=Cl,Br或I;R为C1~C17的饱和脂肪烃、脂环烃、苯基烷基;
所述有机溶剂为苯、甲苯、二甲苯、均三甲苯、氯苯、邻二氯苯、间二氯苯、对二氯苯、氟苯、五氟苯、六氟苯、乙酸乙酯、乙酸叔丁酯、乙酸丙酯、乙腈、苯腈、四氢呋喃、乙醚和1,4-二氧六环中的一种或几种的混合物;所述的催化剂为Fe(OAc)2、Cu(OAc)2、Co(OAc)2、Mn(OAc)2、Pd(OAc)2、PdCl2、PdCl2(PPh3)2、Pd2(dba)3、Ni(acac)2、Fe(acac)2、Fe(OTf)2、Fe(acac)3、Fe(OTf)3、FeCl3和FeCl2中的一种或几种的混合物;所述稳定剂为聚乙烯吡咯烷酮;所述的碱为醋酸钾、醋酸钠、醋酸铯、碳酸钾、碳酸钠、碳酸氢钾、碳酸氢钠、氢氧化钠、氢氧化钾、磷酸钠、磷酸钾、磷酸氢钠、磷酸氢钾、三乙胺、吡啶、二异丙基乙基胺和N-甲基吗啡啉的一种或者几种的混合物;所述还原剂为甲醇、乙醇、异丙醇、丁醇,乙二醇,1,3-丙二醇,1,2-丙二醇,丙三醇,1,4丁二醇,葡萄糖和甘露糖中的一种或几种的混合物。
3.根据权利要求1所述的一种5,5’-二烷氧酰基-[2,2’]联呋喃类化合物的制备方法,其特征在于,所述回流反应的温度为25℃~160℃。
4.根据权利要求1所述的一种5,5’-二烷氧酰基-[2,2’]联呋喃类化合物的制备方法,其特征在于,所述回流反应的时间为1~60小时。
5.根据权利要求1所述的一种5,5’-二烷氧酰基-[2,2’]联呋喃类化合物的制备方法,其特征在于,所述聚乙烯吡咯烷酮的分子量为1~10万。
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Synthesis of [2,2’]Bifuranyl-5,5’-dicarboxylic Acid Esters via Reductive Homocoupling of 5-Bromofuran-2-carboxylates Using Alcohols as Reductants;Yi Xie et al.;《Chin. J. Chem.》;20201207;第39卷;第62-68页 * |
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