CN116283645A - 一种偕二酰胺化合物、晶体结构及其制备方法 - Google Patents
一种偕二酰胺化合物、晶体结构及其制备方法 Download PDFInfo
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- 238000000034 method Methods 0.000 claims abstract description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 17
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
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- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
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- 239000010437 gem Substances 0.000 description 1
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
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- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/78—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
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Abstract
本发明提供了一种结构新颖的偕二酰胺化合物、偕二酰胺化合物的制备方法及其晶体结构,属于化学物质及其制备技术领域。本发明利用绿色的光催化方法,以廉价的氯化铁作为光催化剂,在可见光照条件下,实现偕二酰胺化合物的合成;同时,本发明为探索其微观结构,培养了该化合物的单晶,并对单晶结构进行解析;所述的偕二酰胺化合物具有一定的发光性能,具有潜在的应用前景。
Description
技术领域
本发明属于化学物质及其制备技术领域,具体涉及一种偕二酰胺化合物、晶体结构及其制备方法。
背景技术
酰胺(acylamide),是酰基与氮原子相连的一类化合物,p-π共轭效应使得酰胺成为高度稳定的化合物,同时由于酰胺氮上取代基的多样性使得不同结构的酰胺活性差异较大。第一,酰胺类化合物是一类良好的有机溶剂,如N,N-二甲基甲酰胺和N,N-二甲基乙酰胺可与水和大多数有机溶剂以及许多无机液体以任意比例混合,是很好的非质子极性溶剂;第二,酰胺类化合物是一系列药物,如含有乙酰氨基的解热镇痛药扑热息痛,含有内酰胺的抗生素类药物青霉素和头孢类药物,含有烟酰胺的维生素B族衍生物等;第三,酰胺类化合物是一系列杀虫剂,对蚜虫尤其高效的氟啶虫酰胺和可分布于整个植株的溴氰虫酰胺等;第四,酰胺可以作为一种重要的精细化学品生产的中间体,作为酰基、氨基等的试剂外,可进一步生产医药、农药、化妆品等。第四,一些含酰胺基团的酰胺聚合物具有良好的荧光性能。因此,构建一种结构新颖的酰胺类化合物将为医药、化工等领域提供基础研究数据。
例如,专利CN201811477901.4公开了一种偕二氟化内酰胺螺苯并五元氮杂环化合物,具有良好的抗TMV活性和杀虫活性。专利CN201811477904.8则公开了一种偕二氟化螺-γ-内酰胺吲哚啉化合物,也具有良好的抗TMV、杀菌和杀虫活性。
此外,由有机分子基本单元构成的具有周期性结构的物质形态称为有机分子晶体。有机化合物在形成晶体结构时,受溶剂、温度、压力、金属离子等因素的影响会形成不同的晶体结构,产生多晶现象,这种结构上的变化,会导致其性能的变化。因此,探索晶体结构为酰胺类物质在医药、材料等领域的研究具有十分重要的意义。
发明内容
针对上述不足,本发明提供了一种偕二酰胺化合物、晶体结构及其制备方法。本发明所述的偕二酰胺化合物具有一定的发光性能,具有潜在的应用前景。
为了实现上述发明目的,本发明的技术方案如下:
一方面,本发明提供了一种偕二酰胺化合物,所述的化合物的分子式为C16H16N2O2,结构简式如下式Ⅰ:
又一方面,本发明提供了上述偕二酰胺化合物的制备方法,所述的制备方法的反应方程式如下:
具体地,所述的制备方法包括以下步骤:
在LED灯光照射下,以乙腈为溶剂、FeCl3为催化剂,氮气保护下、在过氧叔丁醇存在下,乙醚与N-亲核试剂苯甲酰胺发生氨化反应,用乙酸乙酯和水萃取后,干燥浓缩,用硅胶柱层析得到目标白色粉末。
通过1HNMR、高分辨质谱(HRMS)对产物做了表征。
具体地,所述的晶体的结构中C1-C6苯环与C11-C16苯环平面形成48.845(272)°的夹角;每个分子通过C3-H3···O2 i氢键作用形成一维链结构, ∠C3-H3···O2 i=132.204(533)°,(i=x,y-1,z)相邻的一维链通过芳环堆积形成二位层结构和三维超分子结构。
又一方面,本发明提供了上述偕二酰胺化合物的晶体的制备方法,所述的晶体采用挥发化合物饱和溶液法制得。
具体地,所述的制备方法包括以下步骤:取式Ⅰ化合物溶解于二氯甲烷中,得到无色透明溶液,室温下静止,待自然挥发,杯底产生无色透明的块状单晶,即为所述的偕二酰胺化合物的晶体。
具体地,所述的室温的温度为20-40℃。
与现有技术相比,本发明具有如下的有益效果:
本发明提供了一种偕二酰胺化合物及其晶体结构,为探索微观结构提供数据支持。本发明利用绿色的光催化方法,以廉价的氯化铁作为光催化剂,在可见光照条件下,实现偕二酰胺化合物的合成;同时,本发明为探索其微观结构,培养了该化合物的单晶,并对单晶结构进行解析。所述的偕二酰胺化合物具有一定的发光性能,具有潜在的应用前景。
附图说明
图1为式Ⅰ化合物的分子结构图。
图2为式Ⅰ化合物的三维堆积图。
图3为式Ⅰ化合物的1HNMR图。
图4为式Ⅰ化合物的高分辨质谱(HRMS)图。
图5为式Ⅰ化合物的二氯甲烷溶液的发射光谱图(257nm激发)。
具体实施方式
下面结合具体实施例,对本发明作进一步详细的阐述,下述实施例不用于限制本发明,仅用于说明本发明。以下实施例中所使用的实验方法如无特殊说明,实施例中未注明具体条件的实验方法,通常按照常规条件,下述实施例中所使用的材料、试剂等,如无特殊说明,均可从商业途径得到。
其次,此处所称的“一个实施例”或“实施例”是指可包含于本发明至少一个实现方式中的特定特征、结构或特性。在本说明书中不同地方出现的“在一个实施例中”并非均指同一个实施例,也不是单独的或选择性的与其他实施例互相排斥的实施例。
实施例1.式Ⅰ化合物的制备
在10mL的拧口瓶中加入苯甲酰胺1a(0.3mmol,36.3mg),氯化铁(2.4mg,5%),后拧口瓶中的空气通过Schlenk装置置换成氮气,再用注射器加入过氧叔丁醇(0.9mmol,165μL)的溶液(3mL,乙醚:乙腈=1:1)。然后,将上述反应瓶置于20W(波长=450-455nm)的LED灯下,照射20h。反应结束后,反应液用乙酸乙酯和水萃取3次,所得混合经过干燥浓缩,用硅胶柱层析(洗脱剂为石油醚:乙酸乙酯5:1到2:1)得产物I14mg,产率为35%。1HNMR(400MHz,Chloroform-d):δ7.78(d,J=7.3Hz,4H),7.58(d,J=7.5Hz,2H),7.50(t,J=7.4Hz,2H),7.41(t,J=7.6Hz,4H),5.73(m,1H),1.81(d,J=6.8Hz,3H).HRMS(ESI):C16H16N2O2[M+Na]+的m/z理论值:291.1009;实测值:291.1009。
实施例2.式Ⅰ化合物晶体的制备
采用挥发化合物饱和溶液法制得,具体制备步骤为:取0.27g(约1mmol)式Ⅰ化合物溶解在10mL二氯甲烷溶解,得到无色透明溶液,然后在室温下(20-40℃)静止,待自然挥发,杯底产生无色透明的块状单晶,即为所述的偕二酰胺化合物的晶体。
将目标产物晶体进行X-射线衍射数据的测定,在Bruker smart Apex CCD II面探单晶衍射仪上,用MoK射线以ω扫描方式共收集配合物X-射线衍射数据。衍射强度数据经Lp因子和经验吸收校正。全部非氢原子和氢原子采用直接法获得,非氢原子坐标及其各向异性温度因子采用全矩阵最小二乘法修正,计算工作在PC机上用OLEX程序包完成,主要晶体学数据见下表1所示,主要键角数据见表2所示,其分子结构图和三维堆积图详见附图1和附图2。
表1配位物晶体学参数表
a)R1=Σ(|Fo|–|Fc|)/∑|Fo|,wR2=[Σw(Fo 2–Fc 2)2/Σw(Fo 2)2]1/2
b)w=[2(Fo 2)+(AP)2+BP]–1withP=(Fo 2+2Fc 2)/3。
表2
N1 C7 C6 | 117.4(6)° | C7 N1 C8 | 122.1(5)° | N1 C8 N2 | 111.1(5)° |
N1 C8 C9 | 110.7(5)° | N2 C8 C9 | 109.7(5)° | C10 N2 C8 | 121.7(6)° |
N2 C10 C11 | 117.7(6)° | O1 C7 C6 | 120.2(6)° | O2 C10 C11 | 121.0(6)° |
荧光光谱的测定:
荧光光谱在上海天美FL970荧光分光光度计上测定。用二氯甲烷为溶剂配制1mmol/L的溶液,于石英比色皿中在荧光光谱仪上测绘荧光发射光谱。设置激发狭缝2.5nm,发射狭缝2.5nm,扫描速度240nm/min,采样间隔1nm,扫描范围280-550nm,用波长278nm为激发,测得发射光谱,见图5。表明,产物的二氯甲烷溶液激发波长在278nm,在305nm有最大发射波长,在357nm,372nm处也有较大发射波长。该实验表明,该化合物存在潜在的发紫光及蓝光的潜在应用。
以上所述实施例仅表达了本发明的几种实施方式,其描述较为具体和详细,但并不能因此而理解为对本发明专利范围的限制。应当指出的是,对于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。因此,本发明专利的保护范围应以所附权利要求为准。
Claims (7)
3.根据权利要求2所述的制备方法,其特征在于:所述的制备方法包括以下步骤:在LED灯光照射下,以乙腈为溶剂、FeCl3为催化剂,氮气保护下、在过氧叔丁醇存在下,乙醚与N-亲核试剂苯甲酰胺发生氨化反应,用乙酸乙酯和水萃取后,干燥浓缩,用硅胶柱层析得到目标白色粉末。
6.一种权利要求4-5任一项所述的晶体的制备方法,其特征在于:所述的晶体采用挥发化合物饱和溶液法制得。
7.根据权利要求6所述的制备方法,其特征在于:所述的制备方法包括以下步骤:取式Ⅰ化合物溶解于二氯甲烷中,得到无色透明溶液,室温下静止,待自然挥发,杯底产生无色透明的块状单晶,即为所述的偕二酰胺化合物的晶体。
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