CN107056684A - 一种2,2’,3,3’—四羟基联萘与4,4’—联吡啶形成的共晶及制备方法 - Google Patents

一种2,2’,3,3’—四羟基联萘与4,4’—联吡啶形成的共晶及制备方法 Download PDF

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CN107056684A
CN107056684A CN201710350500.1A CN201710350500A CN107056684A CN 107056684 A CN107056684 A CN 107056684A CN 201710350500 A CN201710350500 A CN 201710350500A CN 107056684 A CN107056684 A CN 107056684A
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dinaphthalene
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tetrahydroxy
bipyridyl
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吉保明
邓冬生
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Luoyang Normal University
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
    • C07C39/14—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with at least one hydroxy group on a condensed ring system containing two rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/127—Preparation from compounds containing pyridine rings
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    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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    • C07B2200/13—Crystalline forms, e.g. polymorphs

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Abstract

本发明公开了一种2,2’,3,3’—四羟基联萘与4,4’—联吡啶形成的共晶及制备方法。所述共晶由1个2,2’,3,3’—四羟基—1,1’—联萘分子和1个4,4’—联吡啶分子通过O‑H···N氢键的作用形成共晶基本结构单元，晶体中的2,2’,3,3’—四羟基—1,1’—联萘分子通过分子间的O—H···O的氢键形成一维螺旋链，4,4’—联吡啶分子通过O—H···N氢键连接在一维螺旋链上形成二维层状结构，整体结构表现为2,2’,3,3’—四羟基—1,1’—联萘分子形成的螺旋链包合4,4’—联吡啶分子。所述制备方法以乙腈和三氯甲烷为溶剂，采用溶液冷却结晶方法制得共晶。本发明提供了多元酚与吡啶类物质形成共晶的制备方法，为该类药物共晶制备提供理论指导意义。

Description

一种2,2’,3,3’—四羟基联萘与4,4’—联吡啶形成的共晶及 制备方法
技术领域
本发明属于多酚类化合物与含吡啶类化合物的共晶技术领域，具体涉及到一种2,2’,3,3’—四羟基联萘与4,4’—联吡啶形成的共晶及制备方法。
背景技术
第一个共晶是WÖhler于1844年制备的氢醌共晶，1967年Schmidt和Snipes两人最先用“共晶”这个词来描述嘧啶和嘌呤的复合物分子。之后，共晶概念一直在不断的更新含义，直到2003年，一个较为普遍的接受概念就是共晶作为一种同相的结晶材料，它含有化学计量的两种或者两种以上的中性组份。
超分子化学和晶体工程概念认为共晶是一种超分子自组装体系，是热力学、动力学和分子识别三者之间相互作用而达到平衡的一个最稳定的结果。对近100多年所制备的共晶的研究发现，共晶的形成作用力主要来自于氢键、卤键、π-π堆积作用和电荷交换等作用力。研究发现，共晶结构中各组份之间不单单只存在一种作用力，而是由各种不同的作用力共同发挥作用，达到平衡后形成稳定的晶体。
作为一个较为新颖的研究领域，共晶研究目前依然遇到不少挑战。首先遇到的挑战就是，对共晶形成的形成机理不是完全掌握，这主要是因为不是任何两种组份都能形成共晶，所以必然存在何种组份能够形成结晶以及有多少种组份能够共组装结晶等等问题。这就有必要继续研究有关共晶结晶的方法问题，包括溶剂的选择、结晶方法的选择、组份的选择和化学技巧等。
发明内容
本发明的目的是提供一种2,2’,3,3’—四羟基联萘与4,4’—联吡啶形成的
共晶及制备方法，为该类药物共晶制备提供理论指导。
本发明的目的可采用如下技术方案来实现：
一种2,2’,3,3’—四羟基联萘与4,4’—联吡啶形成的共晶，其结构特征如下：由1个2,2’,3,3’—四羟基—1,1’—联萘分子和1个4,4’—联吡啶分子通过O—H···N氢键作用形成共晶基本结构单元，晶体中的2,2’,3,3’—四羟基—1,1’—联萘分子通过分子间的O—H···O氢键形成一维螺旋链，4,4’—联吡啶分子通过O—H···N氢键连接在一维螺旋链上形成二维层状结构，整体结构表现为2,2’,3,3’—四羟基—1,1’—联萘分子形成的螺旋链包合4,4’—联吡啶分子。
所述的2,2’,3,3’—四羟基联萘与4,4’—联吡啶形成的共晶属于三斜晶系，空间群为Pī，晶胞参数为a = 10.9784(14)Ǻ，b = 11.0143(14)Ǻ， c = 12.231(3)Ǻ，三个轴角α = 106.725(2)°，β = 97.641(2)°，γ= 119.202(10)°，V = 1168.4(3)Ǻ3。
本发明得到的2,2’,3,3’—四羟基联萘与4,4’—联吡啶形成的共晶是以乙腈或三氯甲烷为溶剂，采用溶剂冷却结晶的方式制备得到，其具体制备方法步骤如下：
（1）将摩尔比为2:1~1:2的2,2’,3,3’—四羟基—1,1’—联萘和4,4’—联吡啶加入到圆底烧瓶中，同时加入乙腈溶剂或者三氯甲烷溶剂并放入磁力搅拌子，体系中溶质总含量比例为1.0% ~10.0%；
（2）装上回流装置，搅拌下加热回流，直到溶质完全溶解；
（3）将得到的溶液过滤，滤液在室温下放置，让其自然挥发，数天后析出大量无色晶体；
（4）将析出的晶体过滤，自然晾干得到2,2’,3,3’—四羟基—1,1’—联萘与4,4’—联吡啶形成的共晶。
所述2,2’,3,3’—四羟基—1,1’—联萘与4,4’—联吡啶形成共晶的摩尔比为1:1。
本发明提供了多元酚与吡啶类物质形成的共晶及制备方法，为该类药物共晶制备提供理论指导。
附图说明
图1为2,2’,3,3’—四羟基—1,1’—联萘与4,4’—联吡啶形成的共晶不对称结构单元
图2为2,2’,3,3’—四羟基—1,1’—联萘分子形成的一维螺旋链图
图3为2,2’,3,3’—四羟基—1,1’—联萘分子包合4,4’—联吡啶分子结构图。
具体实施方式
本发明实施例所选用共晶结晶组份为2,2’,3,3’—四羟基—1,1’—联萘与4,4’—联吡啶，溶剂为乙腈或者三氯甲烷。
本发明用到的组份2,2’,3,3’—四羟基—1,1’—联萘，分子式为C20H14O4，其结构式如a所示。组份4,4’—联吡啶，分子式为C10H8N2，其结构式如b所示
如图1所示：不对称晶胞中含有1个2,2’,3,3’—四羟基—1,1’—联萘分子与1个4,4’—联吡啶分子。
如图2和图3所示：由1个2,2’,3,3’—四羟基—1,1’—联萘分子和1个4,4’—联吡啶分子通过O—H···N氢键作用形成共晶基本结构单元，晶体中的12,2’,3,3’—四羟基—1,1’—联萘分子通过分子间的O—H···O氢键形成一维螺旋链，4,4’—联吡啶分子通过O—H···N氢键连接在一维螺旋链上形成二维层状结构，整个共晶结构表现为2,2’,3,3’—四羟基—1,1’—联萘分子形成的螺旋链包合4,4’—联吡啶分子。2,2’,3,3’—四羟基—1,1’—联萘与4,4’—联吡啶形成共晶的摩尔比为1:1.。
上述2,2’,3,3’—四羟基—1,1’—联萘与4,4’—联吡啶形成共晶的制备方法如以下实施例：
实施例1：
将1.0 mmol 2,2’,3,3’—四羟基—1,1’—联萘（318毫克）、1.0 mmol 4,4’—联吡啶（156毫克）置于50 mL圆底烧瓶中，两者的摩尔比为1:1，再加入30 mL乙腈，固体占体系总质量2.0%。放入一个磁子，装上回流冷凝管，搅拌下加热回流1小时，趁热过滤，滤液放置在室温下让其自然挥发，数天后从滤液中析出大量无色晶体，过滤，得到分子式为C30H22N2O4共晶，称重质量为455毫克，产率为96%。
2,2’,3,3’—四羟基—1,1’—联萘与4,4’—联吡啶形成的共晶表征过程如下：
（1）2,2’,3,3’—四羟基—1,1’—联萘与4,4’—联吡啶形成的共晶单晶结构测定
选取大小合适的晶体粘于一根玻璃丝上，放置在Bruker SMART ApexII单晶衍射仪上进行单晶结构测定： 23℃下，以MoK a (λ= 0.71073 Å)射线作为光源，石墨作为单色器，检测面板为Bruker Smart CCD，采用ω扫描方式对晶胞进行扫描测定，并收集衍射强度数据。首先采用BrukerAPEX-II 程序对采集好的数据进行晶胞精修、数据的吸收校正以及还原；然后通过 SHELXTL 软件中的 XS 程序对还原后的数据采用直接法解析结构，获得所有非氢原子的初始相位角，各向异性参数的精修则通过SHELXL-97 程序运行，使用全矩阵最小二乘法，直至数据收敛，最终对非氢原子坐标的进行确定。芳香环上与碳原子相连的氢以及氧原子上的氢原子均通过理论计算法加入。详细的晶体测试参数如下表所示：
（3）2,2’,3,3’—四羟基—1,1’—联萘与4,4’—联吡啶形成共晶的元素分析测试
使用意大利产的Flash EA-2000元素分析仪对2,2’,3,3’—四羟基—1,1’—联萘与4,4’—联吡啶形成的共晶进行元素分析，测试结果表明C、N、H三元素的测定值与理论值相近，其测试结果数据如下：对分子式为C30H22N2O4的共晶分析，其理论值为：C 75.94, H 4.67, N5.90; 实测值：C 76.21, H 4.83, N 5.98.
实施例2：
将2.0 mmol 2,2’,3,3’—四羟基—1,1’—联萘（636毫克）、1.0 mmol 4,4’—联吡啶（156毫克）置于50 mL圆底烧瓶中，两者的摩尔比为2:1，再加入30 mL乙腈，固体占体系总质量的3.3%。放入一个磁子，装上回流冷凝管，搅拌下加热回流1小时，趁热过滤，滤液放置在室温下让其自然挥发，数天后从滤液中析出大量无色晶体，过滤，得到分子式为C30H22N2O4共晶，称重质量为446毫克，产率为94%。
实施例3：
将1.0 mmol 2,2’,3,3’—四羟基—1,1’—联萘（318毫克）、2.0 mmol 4,4’—联吡啶（312毫克）置于50 mL圆底烧瓶中，两者的摩尔比为1:2，再加入30 mL乙腈，固体占体系总质量的2.6%。放入一个磁子，装上回流冷凝管，搅拌下加热回流1小时，趁热过滤，滤液放置在室温下让其自然挥发，数天后从滤液中析出大量无色晶体，过滤，得到分子式为C30H22N2O4共晶，称重质量为431毫克，产率为91%。
实施例4：
将1.0 mmol 2,2’,3,3’—四羟基—1,1’—联萘（318毫克）、1.0 mmol 4,4’—联吡啶（156毫克）置于50 mL圆底烧瓶中，两者的摩尔比为1:1，再加入15 mL乙腈，固体占体系总质量的3.9%。放入一个磁子，装上回流冷凝管，搅拌下加热回流1小时，趁热过滤，滤液放置在室温下让其自然挥发，一天后从滤液中析出大量无色晶体，过滤，得到分子式为C30H22N2O4共晶，称重质量为450毫克，产率为95%。
实施例5
将1.0 mmol 2,2’,3,3’—四羟基—1,1’—联萘（318毫克）、1.0 mmol 4,4’—联吡啶（156毫克）置于50 mL圆底烧瓶中，两者的摩尔比为1:1，再加入20 mL三氯甲烷，固体占体系总质量1.6%。放入一个磁子，装上回流冷凝管，搅拌下加热回流0.5小时，趁热过滤，滤液放置在室温下让其自然挥发，24小时后从滤液中析出大量无色晶体，过滤，得到分子式为C30H22N2O4共晶，称重质量为417毫克，产率为88%。
实施例6：
将2.0 mmol 2,2’,3,3’—四羟基—1,1’—联萘（636毫克）、1.0 mmol 4,4’—联吡啶（156毫克）置于50 mL圆底烧瓶中，两者的摩尔比为2:1，再加入20 mL三氯甲烷，固体占体系总质量2.6%。放入一个磁子，装上回流冷凝管，搅拌下加热回流0.5小时，趁热过滤，滤液放置在室温下让其自然挥发，24小时后从滤液中析出大量无色晶体，过滤，得到分子式为C30H22N2O4共晶，称重质量为426毫克，产率为90%。
实施例7：
将1.0 mmol 2,2’,3,3’—四羟基—1,1’—联萘（318毫克）、2.0 mmol 4,4’—联吡啶（312毫克）置于50 mL圆底烧瓶中，两者的摩尔比为1:2，再加入20 mL三氯甲烷，固体占体系总质量2.1%。放入一个磁子，装上回流冷凝管，搅拌下加热回流0.5小时，趁热过滤，滤液放置在室温下让其自然挥发，24小时后从滤液中析出大量无色晶体，过滤，得到分子式为C30H22N2O4共晶，称重质量为436毫克，产率为92%。

Claims (4)

1.一种2,2’,3,3’—四羟基联萘与4,4’—联吡啶形成的共晶，其特征是：由1个2,2’,3,3’—四羟基—1,1’—联萘分子和1个4,4’—联吡啶分子通过O—H···N氢键的作用形成共晶基本结构单元，晶体中的2,2’,3,3’—四羟基—1,1’—联萘分子通过分子间的O—H···O氢键形成一维螺旋链，4,4’—联吡啶分子通过O-H···N氢键连接在一维螺旋链上形成二维层状结构，表现为2,2’,3,3’—四羟基—1,1’—联萘分子形成的螺旋链包合4,4’—联吡啶分子。
2.根据权利要求1所述的一种2,2’,3,3’—四羟基联萘与4,4’—联吡啶形成的共晶，其特征在于：所述的共晶属于三斜晶系，空间群为Pī，晶胞参数为a = 10.9784(14)Ǻ，b =11.0143(14)Ǻ， c = 12.231(3)Ǻ，三个轴角α = 106.725(2)°，β = 97.641(2)°，γ =119.202(10)°，V = 1168.4(3)Ǻ3。
3.一种如权利要求1所述的2,2’,3,3’—四羟基联萘与4,4’—联吡啶形成的共晶的制备方法，其特征是：以乙腈或三氯甲烷为溶剂，采用溶液冷却结晶的方法，具体步骤如下：
（1）将摩尔比为2:1~1:2的2,2’,3,3’—四羟基—1,1’—联萘和4,4’—联吡啶加入到圆底烧瓶中，同时加入乙腈溶剂或者三氯甲烷溶剂并放入磁力搅拌子，体系中溶质总含量比例为1.0%~10.0%；
（2）装上回流装置，搅拌下加热回流，直到溶质完全溶解；
（3）将得到的溶液过滤，滤液在室温下放置，让其自然挥发，数天后析出大量无色晶体；
（4）将析出的晶体过滤，自然晾干得到2,2’,3,3’—四羟基—1,1’—联萘与4,4’—联吡啶形成的共晶。
4.根据权利要求3所述的一种2,2’,3,3’—四羟基联萘与4,4’—联吡啶形成的共晶的制备方法，其特征是：所述2,2’,3,3’—四羟基—1,1’—联萘与4,4’—联吡啶形成共晶的摩尔比为1:1。
CN201710350500.1A 2017-05-18 2017-05-18 一种2,2’,3,3’—四羟基联萘与4,4’—联吡啶形成的共晶及制备方法 Pending CN107056684A (zh)

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