CN107474089A - 手性葡糖双齿氮杂环卡宾前体盐及其制备方法和用途 - Google Patents

手性葡糖双齿氮杂环卡宾前体盐及其制备方法和用途 Download PDF

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CN107474089A
CN107474089A CN201710730269.9A CN201710730269A CN107474089A CN 107474089 A CN107474089 A CN 107474089A CN 201710730269 A CN201710730269 A CN 201710730269A CN 107474089 A CN107474089 A CN 107474089A
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precursor salt
carbene precursor
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周中高
元洋洋
蓝倩
谢永荣
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Gannan Normal University
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Abstract

本发明提供了一种手性葡糖双齿氮杂环卡宾前体盐及其制备方法和用途，结构如式I所示：

Description

手性葡糖双齿氮杂环卡宾前体盐及其制备方法和用途
技术领域
本发明涉及一种手性葡糖双齿氮杂环卡宾前体盐及其制备方法和用途，属于有机合成技术领域。
背景技术
与双齿氮杂环卡宾相比，单一氮杂环卡宾虽然是优良的供电子体，但是氮原子上取代基比较单一，很多时候都是在氮原子上引入位阻一般的基团，使得催化活性不高，同时引入的手性源也过于单一，在不对称催化反应中表现出比较差的立体选择性。超支化聚合反应是制备超支化聚合物的一种聚合反应，但是在超支化聚合反应中非常容易发生副反应导致凝胶而使反应无法进行，生成副产物，造成不必要的浪费，归结起来超支化聚合反应副反应多，难于精准控制超支化聚合反应的聚合度和支化度。要获得理想的超支化聚合物，避免副反应、精准控制超支化咔唑聚合物的聚合度、支化度、分子量、纯度、以及金属残余量，必须制备高活性、反应易控、产物易分离纯化的新型催化剂。
发明内容
针对现有技术中的缺陷，本发明的目的是提供一种手性葡糖双齿氮杂环卡宾前体盐及其制备方法和用途。
本发明是通过以下技术方案实现的：
一种手性葡糖双齿氮杂环卡宾前体盐，其结构如式I所示：
一种如前述的手性葡糖双齿氮杂环卡宾前体盐的制备方法，其包括如下步骤：
将1-(2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基)咪唑与1,3-二溴丙烷在无水四氢呋喃中、惰性气体保护下，回流反应，得到式II所示化合物；
将式II所示化合物与N-苄基咪唑在无水四氢呋喃中、惰性气体保护下，回流反应，得到所述手性葡糖双齿氮杂环卡宾前体盐；
反应路线为：
作为优选方案，所述1-(2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基)咪唑与1,3-二溴丙烷的摩尔比为1:(1～5)，式II所示化合物与N-苄基咪唑的摩尔比为1:(1～5)。
一种如前述的手性葡糖双齿氮杂环卡宾前体盐的制备方法，其包括如下步骤：
将N-苄基咪唑与1,3-二溴丙烷在无水四氢呋喃中、惰性气体保护下，回流反应，得到式III所示化合物；
将式III所示化合物与1-(2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基)咪唑在无水四氢呋喃中、惰性气体保护下，回流反应，得到所述手性葡糖双齿氮杂环卡宾前体盐；
反应路线为：
作为优选方案，所述N-苄基咪唑与1,3-二溴丙烷的摩尔比为1：(1～5)；式III化合物与1-(2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基)咪唑的摩尔比为1:(1～5)。
一种如前述的手性葡糖双齿氮杂环卡宾前体盐在制备超支化咔唑聚合物中的用途；
一种如前述的超支化咔唑聚合物，其结构如式IV所示：
其中，R1为CH3-、CH3CH2-、CH3CH2CH2-、CH3CH2CH2CH2-、Bn-、C5H11CHC6H13；R2为H、4-CH3-、3-CH3-、2-CH3-、4-C6H5-、3-C6H5-、2-C6H5-、4-F-、3-F-、2-F-，取代基前的数字代表该取代基在苯环上的连接位点，如4-CH3-代表甲基连接于苯环的4位碳上(以苯环上与咔唑基相连的碳为1位)。
本发明的通过廉价易得、立体化学丰富的单糖作为催化剂的手性源，用两种不同的路线合成了手性葡糖双齿氮杂环卡宾前体盐，将其作为超支化聚合反应的催化剂，克服超支化聚合反应过程中难以精准控制聚合度和支化度的难题，避免了副反应，成功高效的合成了系列在钙钛矿太阳能电池空穴传输层材料领域具有潜在应用价值的化合物，具体表现在如下方面：
1、含手性葡糖双齿氮杂环卡宾前体盐对该反应具有良好的催化活性和立体选择性，可以高效快速的催化合成系列在钙钛矿太阳能电池空穴传输层材料领域具有潜在应用价值的化合物，所述化合物为超支化咔唑聚合物；
2、针对该反应具有不同取代基的底物，反应均能顺利进行且表现出很高的转化率，显示出手性葡糖双齿氮杂环卡宾前体盐作为催化剂，具有很好的普适性；
3、针对该反应具有钝化取代基的底物，在此也表现较高的转化率，说明该催化剂具有很高的催化活性；
4、该反应涉及的条件温和，反应时间短，后处理方便快捷，产率高；
5、该反应辅助化学品用量小，排放低，绿色环保，符合新旧动能转换理念，具有较高的应用价值。
具体实施方式
下面结合具体实施例对本发明进行详细说明。以下实施例将有助于本领域的技术人员进一步理解本发明，但不以任何形式限制本发明。应当指出的是，对本领域的普通技术人员来说，在不脱离本发明构思的前提下，还可以做出若干变形和改进。这些都属于本发明的保护范围。
实施例1
本实施例涉及一种手性葡糖双齿氮杂环卡宾前体盐的制备方法，其包括如下步骤：
一、在50mL双口圆底烧瓶中依次加入1.0mmol的1-(2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基)咪唑1与3.0mmol的1,3-二溴丙烷，在10mL干燥THF中剧烈回流反应12小时，反应完全后，停止反应，后处理，柱层析提纯，得无色粘稠状化合物II，产率96％,1H NMR(400MHz,CDCl3):δ＝1.97(s,3H),2.02(s,3H),2.04(s,3H),2.06(s,3H),2.55(m,2H),3.44(m,2H),4.15(d,1H,J＝11Hz),4.30(m,1H),4.34(m,1H),4.65(t,2H,J＝6.8Hz),5.23(dd,1H,J＝9.5Hz),5.21(t,1H,J＝2.5Hz),5.48(t,1H,J＝9.5Hz),6.51(d,1H,J＝9.2Hz),7.68(s,1H,4-Im),7.77(s,1H),11.60(s,1H)；13C NMR(100MHz,CDCl3):δ＝20.47,20.54,20.71,20.79,28.96,32.51,48.79,61.36,67.42,70.86,72.06,74.84,84.00,119.75,123.37,137.3,169.51,169.57,169.86,170.53；MS(ES):m/z(％)＝587(100)[M+1]+；
二、在50mL双口圆底烧瓶中依次加入1.0mmol的化合物II与1.5mmol的N-苄基咪唑，在10mL干燥THF中反应12小时，反应完全后，停止反应，后处理，柱层析提纯得到所述手性葡糖双齿氮杂环卡宾前体盐。1H NMR(400MHz,MeOD)δ9.70(s,1H),9.24(s,1H),7.91(d,J＝1.7Hz,1H),7.85(s,1H),7.74(s,1H),7.61(s,1H),7.47(dd,J＝7.7,1.6Hz,2H),7.39(dt,J＝12.8,4.3Hz,3H),6.06(d,J＝8.9Hz,1H),5.51(t,J＝9.4Hz,1H),5.46(s,2H),5.44-5.37(m,1H),5.28(t,J＝9.6Hz,1H),4.52-4.43(m,2H),4.43-4.32(m,2H),4.29(dt,J＝8.8,5.5Hz,2H),4.20(t,J＝7.0Hz,1H),2.64-2.45(m,2H),2.01(s,3H),2.01(s,3H),1.97(s,3H),1.94(s,3H).13C NMR(101MHz,MeOD)δ170.79,169.83,169.75,169.68,136.08,133.53,128.88,128.84,128.50,122.83,122.63,122.49,120.94,84.52,74.80,71.85,71.39,67.50,61.36,52.81,29.93,19.28,19.09,19.02,18.97。
实施例2
本实施例涉及一种手性葡糖双齿氮杂环卡宾前体盐的制备方法，其包括如下步骤：
一、在50mL双口圆底烧瓶中依次加入1.0mmol的N-苄基咪唑与3.0mmol的1,3-二溴丙烷，在10mL干燥THF中反应12小时，反应完全后，停止反应，后处理，柱层析提纯得化合物III。1H NMR(400MHz,CDCl3)δ9.98(s,1H),7.52(s,1H),7.32(s,1H),7.25(m,2H),7.06(m,3H),5.34(s,2H),4.27(t,J＝8.0Hz,2H),3.18(t,J＝8.0Hz,2H),2.22(m,2H).13C NMR(101MHz,CDCl3)δ136.17,132.92,129.11,129.05,128.72,122.78,122.07,52.86,48.07,32.29,29.12；
二、在50mL双口圆底烧瓶中依次加入1.0mmol的化合物III与1.5mmol的1-(2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基)咪唑，在10mL干燥THF中反应12小时，反应完全后，停止反应，后处理，柱层析提纯得得到所述手性葡糖双齿氮杂环卡宾前体盐。1H NMR(400MHz,MeOD)δ9.70(s,1H),9.24(s,1H),7.91(d,J＝1.7Hz,1H),7.85(s,1H),7.74(s,1H),7.61(s,1H),7.47(dd,J＝7.7,1.6Hz,2H),7.39(dt,J＝12.8,4.3Hz,3H),6.06(d,J＝8.9Hz,1H),5.51(t,J＝9.4Hz,1H),5.46(s,2H),5.44-5.37(m,1H),5.28(t,J＝9.6Hz,1H),4.52-4.43(m,2H),4.43-4.32(m,2H),4.29(dt,J＝8.8,5.5Hz,2H),4.20(t,J＝7.0Hz,1H),2.64-2.45(m,2H),2.01(s,3H),2.01(s,3H),1.97(s,3H),1.94(s,3H).13C NMR(101MHz,MeOD)δ170.79,169.83,169.75,169.68,136.08,133.53,128.88,128.84,128.50,122.83,122.63,122.49,120.94,84.52,74.80,71.85,71.39,67.50,61.36,52.81,29.93,19.28,19.09,19.02,18.97。
实施例3
本实施例涉及一种利用实施例1得到的手性葡糖双齿氮杂环卡宾前体盐催化制备超支化聚合物的方法，具体包括如下步骤：
将手性葡糖双齿氮杂环卡宾前体盐(1.1mmol％)，PdCl2(1mmol％)，碱助剂K2CO3(6.0mmol)，3,6-二溴-9-(4-溴苯基)-9H-咔唑(2.0mmol)和2,7-双(4,4,5,5-四甲基-1,3,2-二氧杂戊硼环-2-基)-9-(十一烷-5-基)-9H-咔唑(3.0mmol)置于50mL双口圆底烧瓶中，通过置换，使体系充满氮气，然后加入10mL脱氧丙酮/水(V/V＝3/1)，加热到110℃，保持1.5h，然后加入封端剂4-甲基苯硼酸，继续在110℃反应4h。将反应混合液倒入干燥的甲醇中，析出固体，过滤。将固体继续溶解于无水THF，将不容物虑除，蒸除溶剂，得灰色固体，继续将其溶解在无水THF中，所得溶液滴入无水甲醇，析出固体，过滤，如此反复三次，得最终产物IV-1，产率80％；
反应路线为：
产物为灰色固体，Mw＝6.8×103，PDI＝2.33(GPC，聚苯乙烯校准)。HB-Cz的1H NMR(400MHz,CDCl3)：δ(ppm)0.80-0.84(-CH3),1.17-1.33(-CH2-),1.56(-CH2),2.06(-CH2),2.26(-CH3),4.78(-N-CH-),7.31-7.80(Ar-H),8.19-8.59(Ar-H).13C NMR(400MHz,CDCl3):δ(ppm)14.03,22.60,23.66,26.93,29.23,29.37,29.50,31.76,33.87,56.43,107.61,110.20,127.00,127.08,127.27,127.36,127.84,128.80,129.00,129.93,134.88,136.57,137.75,139.87,140.29,140.78,141.42,142.54,143.26。
以上对本发明的具体实施例进行了描述。需要理解的是，本发明并不局限于上述特定实施方式，本领域技术人员可以在权利要求的范围内做出各种变形或修改，这并不影响本发明的实质内容。

Claims (7)

1.一种手性葡糖双齿氮杂环卡宾前体盐，其特征在于，结构如式I所示：
2.一种如权利要求1所述的手性葡糖双齿氮杂环卡宾前体盐的制备方法，其特征在于，包括如下步骤：
将1-(2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基)咪唑与1,3-二溴丙烷在无水四氢呋喃中、惰性气体保护下，回流反应，得到式II所示化合物
将式II所示化合物与N-苄基咪唑在无水四氢呋喃中、惰性气体保护下，回流反应，得到所述手性葡糖双齿氮杂环卡宾前体盐。
3.如权利要求2所述的手性葡糖双齿氮杂环卡宾前体盐的制备方法，其特征在于，所述1-(2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基)咪唑与1,3-二溴丙烷的摩尔比为1:(1～5)，式II所示化合物与N-苄基咪唑的摩尔比为1:(1～5)。
4.一种如权利要求1所述的手性葡糖双齿氮杂环卡宾前体盐的制备方法，其特征在于，包括如下步骤：
将N-苄基咪唑与1,3-二溴丙烷在无水四氢呋喃中、惰性气体保护下，回流反应，得到式III所示化合物
将式III所示化合物与1-(2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基)咪唑在无水四氢呋喃中、惰性气体保护下，回流反应，得到所述手性葡糖双齿氮杂环卡宾前体盐。
5.如权利要求4所述的手性葡糖双齿氮杂环卡宾前体盐的制备方法，其特征在于，所述N-苄基咪唑与1,3-二溴丙烷的摩尔比为1：(1～5)；式III化合物与1-(2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基)咪唑的摩尔比为1:(1～5)。
6.一种如权利要求1所述的手性葡糖双齿氮杂环卡宾前体盐在制备超支化咔唑聚合物中的用途。
7.一种如权利要求6所述的超支化咔唑聚合物，其特征在于，结构如式IV所示：
其中，R1为CH3-、CH3CH2-、CH3CH2CH2-、CH3CH2CH2CH2-、Bn-、C5H11CHC6H13；R2为H、4-CH3-、3-CH3-、2-CH3-、4-C6H5-、3-C6H5-、2-C6H5-、4-F-、3-F-、2-F-。
CN201710730269.9A 2017-08-23 2017-08-23 手性葡糖双齿氮杂环卡宾前体盐及其制备方法和用途 Pending CN107474089A (zh)

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