CN108947953B - 一种黄酮类衍生物的合成方法 - Google Patents
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- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
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Abstract
一种黄酮类衍生物的合成方法,是以邻炔丙醇苯酚为原料,于室温条件下加入有机溶剂充分溶解,而后加入氢碘酸,在40~60℃下反应1~2小时,反应结束后,反应液旋干经硅胶柱层析分离得到目标洗脱液,并让流出液在试管中静置1~48小时后转化得到黄酮类化合物,其中,邻炔丙醇苯酚、氢碘酸的物质的量之比为1:1.5~2;所述的有机溶剂为C1~C4的卤代烃或乙腈、硝基甲烷。本发明反应条件温和、操作简便、原料简单易得、反应收率高等特点,具有较好的推广应用前景的合成方法。
Description
技术领域
本发明属于有机合成技术领域,涉及一种黄酮类衍生物的合成方法。
背景技术
黄酮类化合物是一类非常重要的天然产物之一,广泛存在于植物及食物中。到目前为止,已知化学结构的黄酮类化合物至少有4000多种。该类骨架化合物具有非常重要的生物活性和药理作用,如抗炎,抗雌激素,抗氧化剂,抗癌剂,抗艾滋病,抗高血压,抗菌,心血管,抗糖尿病,抗过敏和化学预防等作用。此外,也可以作为食品添加剂制成一系列保健食品。因此,对于黄酮类化合物的合成具有非常重要的应用前景和理论指导,受到有机合成家的关注,成为有机合成化学的重要研究领域之一。
对于黄酮类衍生物的构建发展至今已有很长的历史,纵观其合成方法主要是通过两种合成路线来构建,即查尔酮为底物路线和1,3-丙二酮底物路线。查尔酮路线即邻羟基查尔酮在酸性条件下发生环化反应得到黄酮类化合物;1,3-丙二酮路线通常也是在酸性条件下发生环化反应得到黄酮类化合物;上述所列的方法大都要在回流温度进行,反应时间长,产率不是特别高以及底物适用性不广。
综上所述,开发一种新的合成策略来合成黄酮类化合物显得尤为重要,到目前为止,利用邻炔丙醇苯酚为底物的串联环化反应来制备黄酮未见报道。
发明内容
本发明的目的是提供一种反应条件温和、产率高、操作简便、原料易得的黄酮类衍生物的合成方法。
本发明的一种黄酮类衍生物的合成方法,是以邻炔丙醇苯酚类化合物为原料,邻炔丙醇苯酚类化合物的分子结构式如,于室温条件下加入有机溶剂充分溶解,而后加入氢卤酸,在40~60℃下反应1~2小时,反应结束后,反应液旋干经硅胶柱层析分离得到目标洗脱液,并让流出液在试管中静置1~48小时后转化得到黄酮类化合物,其中,邻炔丙醇苯酚类化合物、氢卤酸的质量之比为1:1.5~2;所述的有机溶剂为C1~C4的卤代烃或乙腈、硝基甲烷,
本发明的一种黄酮类衍生物的合成方法,所述反应的反应式如下:
其中,所述的有机溶剂的质量为邻炔丙醇苯酚类化合物质量的10-30倍,所述的有机溶剂为二氯甲烷。
本发明中,推荐所述的邻炔丙醇苯酚类化合物、氢碘酸的物质的量之比为1:1.5~2,优选1:1.5。
本发明反应过程中以TCL跟踪反应进度及静置时间,推荐所述反应时间为1-2小时,优选1小时,推荐所述静置时间为1-48小时。
本发明中所述的分离纯化采用如下步骤:将反应液加入饱和硫代硫酸钠溶液,再加入乙酸乙酯,充分搅拌后静置分层;分出的水层用乙酸乙酯萃取,将乙酸乙酯的萃取物与分出的有机层合并后分别用饱和食盐水洗涤、无水硫酸钠干燥;蒸除乙酸乙酯溶剂,其后经硅胶柱层析分离纯化得到中间体,而后让流出液在试管中静置1~48小时后,转化得到黄酮类化合物。
本发明与现有技术相比,其有益效果体现在:(1)提供一种新的合成策略来构建;(2)原有的方法反应一般都是在回流温度下进行,本发明的反应条件温和;(3)本发明方法不仅产率高,而且操作简便,底物适用性也广,解决了以前对于不同取代基黄酮类化合物的合成问题;(4)本发明原料简单易得,反应时间短。本发明具有试剂价廉易得、反应条件温和、工艺操作简单、反应时间短、反应收率高等优点,是一种具有较好推广应用前景的黄酮衍生物的合成方法。
具体实施方式
实施例1 :黄酮的制备
代表性的实施过程:室温下,依次向反应瓶中加入邻炔丙醇苯酚-1 (1.12 g, 5mmol)和20 ml 二氯甲烷,然后将氢碘酸(1.0 ml, 7.5 mmol)加入到反应瓶中, 随后将反应置于30℃下反应1小时。TLC跟踪反应进度,反应结束后,将反应液加入饱和硫代硫酸钠溶液,再加入乙酸乙酯,充分搅拌后静置分层;分出的水层用乙酸乙酯萃取,将乙酸乙酯的萃取物与分出的有机层合并后分别用饱和食盐水洗涤、无水硫酸钠干燥;蒸除乙酸乙酯溶剂,其后经硅胶柱层析分离纯化得到中间体,而后让流出液在试管中静置2小时后,转化得到黄酮0.99g, 反应收率90%。
白色固体,mp: 96-98℃. 1H NMR (400 MHz, CDCl3): δ6.85 (s, 1 H), 7.44(t, J = 7.6 Hz, 1 H), 7.52 – 7.60 (m, 4 H), 7.69 – 7.74 (m, 1 H), 7.93 – 7.96(m, 2 H), 8.23 (d, J = 8.0 Hz, 1 H). 13C NMR (100 MHz, CDCl3): δ 107.6, 118.1,124.0, 125.2, 125.7, 126.3, 129.1, 131.6, 131.8, 133.8, 156.3, 163.4, 178.5。
实施例2: 4’-甲基黄酮的制备
室温下,依次向反应瓶中加入邻炔丙醇苯酚-2 (1.42 g, 5 mmol)和20 ml 二氯甲烷,然后将氢碘酸(1.0 ml, 7.5 mmol)加入到反应瓶中, 随后将反应置于30℃下反应1小时,TLC跟踪反应进度,分离纯化步骤同实施例1,得到3’,4’-二甲氧基黄酮1.18g, 反应收率83%。
淡黄色固体,mp: 108-110℃. 1H NMR (400 MHz, CDCl3): δ 6.85 (s, 1 H),7.44 (t, J = 7.6 Hz, 1 H), 7.52 – 7.60 (m, 4 H), 7.69 – 7.74 (m, 1 H), 7.93 –7.96 (m, 2 H), 8.23 (d, J = 8.0 Hz, 1 H). 13C NMR (100 MHz, CDCl3): δ 107.6,118.1, 124.0, 125.2, 125.7, 126.3, 129.1, 131.6, 131.8, 133.8, 156.3, 163.4,178.5。
实施例3: 4’-氯黄酮的制备
室温下,依次向反应瓶中加入邻炔丙醇苯酚-3 (1.29 g, 5 mmol)和20 ml 二氯甲烷,然后将氢碘酸(1.0 ml, 7.5 mmol)加入到反应瓶中, 随后将反应置于30℃下反应1小时。TLC跟踪反应进度。分离纯化步骤同实施例1,得到4’-氯黄酮1.17g, 反应收率91%。
白色固体, mp: 185 - 187℃. 1H NMR (400 MHz, CDCl3): δ 6.81 (s, 1 H),7.42 – 7.46 (m, 1 H), 7.50 – 7.53 (m, 2 H), 7.56 – 7.59 (m, 1 H), 7.70 – 7.74(m, 1 H), 7.88 (dd, J = 2.0, 6.8 Hz, 2 H), 8.23 (dd, J = 1.6, 8.0 Hz, 1 H).13C NMR (100 MHz, CDCl3): δ 107.7, 118.0, 123.9, 125.4, 125.8, 127.6, 129.4,130.3, 133.9, 156.2, 162.3, 178.3。
实施例4:4’-甲氧基黄酮的制备
室温下,依次向反应瓶中加入邻炔丙醇苯酚-4 (1.27 g, 5 mmol)和20 ml 二氯甲烷,然后将氢碘酸(1.0 ml, 7.5 mmol)加入到反应瓶中, 随后将反应置于30℃下反应1小时。TLC跟踪反应进度。分离纯化步骤同实施例1,得到4’-甲氧基黄酮1.12g, 反应收率89%。
淡黄色固体, mp: 157 - 159℃. 1H NMR (400 MHz, CDCl3): δ 3.89 (s, 3 H),6.75 (s, 1 H), 7.02 (d, J = 8.8 Hz, 2 H), 7.41 (t, J = 7.6 Hz, 1 H), 7.55 (d,J = 8.4 Hz, 1 H), 7.66 – 7.71 (m, 1 H), 7.89 (dd, J = 1.6, 7.2 Hz, 2 H), 8.23(dd, J = 1.6, 8.0 Hz, 1 H). 13C NMR (100 MHz, CDCl3): δ 55.5, 106.2, 114.4,117.9, 123.9, 124.0, 125.0, 125.6, 128.0, 133.5, 156.2, 162.4, 163.4, 178.4。
Claims (3)
2.根据权利要求1所述的一种黄酮类衍生物的合成方法,其特征在于:所述的有机溶剂的质量为邻炔丙醇苯酚类化合物质量的10-30倍。
3.根据权利要求1所述的一种黄酮类衍生物的合成方法,其特征在于:所述分离纯化的方法是,将反应液加入饱和硫代硫酸钠溶液,再加入乙酸乙酯,充分搅拌后静置分层;分出的水层用乙酸乙酯萃取,将乙酸乙酯的萃取物与分出的有机层合并后分别用饱和食盐水洗涤、无水硫酸钠干燥;蒸除乙酸乙酯溶剂,其后经硅胶柱层析分离纯化得到中间体,而后让流出液在试管中静置1~48小时后转化,得到黄酮类化合物。
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CN101555240A (zh) * | 2008-04-08 | 2009-10-14 | 温州大学 | 一种黄酮类化合物的化学合成方法 |
CN102000054A (zh) * | 2010-10-26 | 2011-04-06 | 天津医科大学 | 一种黄酮类似物、制备及其作为抗糖尿病药物的用途 |
CN102060826A (zh) * | 2010-12-01 | 2011-05-18 | 江南大学 | 一种7-甲氧基-4'-取代黄酮类化合物的合成方法 |
CN105294627A (zh) * | 2015-11-04 | 2016-02-03 | 江西师范大学 | 一种用1,3-二烷基咪唑金属氧酸盐催化一步合成黄酮类化合物的方法 |
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Patent Citations (4)
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CN101555240A (zh) * | 2008-04-08 | 2009-10-14 | 温州大学 | 一种黄酮类化合物的化学合成方法 |
CN102000054A (zh) * | 2010-10-26 | 2011-04-06 | 天津医科大学 | 一种黄酮类似物、制备及其作为抗糖尿病药物的用途 |
CN102060826A (zh) * | 2010-12-01 | 2011-05-18 | 江南大学 | 一种7-甲氧基-4'-取代黄酮类化合物的合成方法 |
CN105294627A (zh) * | 2015-11-04 | 2016-02-03 | 江西师范大学 | 一种用1,3-二烷基咪唑金属氧酸盐催化一步合成黄酮类化合物的方法 |
Non-Patent Citations (5)
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An efficient approach to 4-chloro quinolines via TMSCl-mediated cascade cyclization of orthopropynol phenyl azides;Xian-Rong Song et al.;《Organic Chemistry Frontiers》;20180321;第5卷(第9期);第1537-1541页 * |
Bronsted acid-mediated cascade cyclization of 2-propynolphenols/anilines leading to 4-halo-2H-chromenes and 1,2-dihydroquinolines;Ren Li et al.;《Tetrahedron Letters》;20170623;第58卷(第31期);第3049-3052页 * |
Convenient and Highly Efficient Routes to 2H-Chromene and 4-Chromanone Derivatives: Iodine-Promoted and p-Toluenesulfonic Acid Catalyzed Cascade Cyclizations of Propynols;Yi-Feng Qiu et al.;《Chemistry-A European Journal》;20150114;第21卷(第8期);第3480-3487页 * |
Highly efficient access to 4-chloro-2H-chromenes and 1,2-dihydroquinolines under mild conditions: TMSCl-mediated cyclization of 2-propynolphenols/anilines;Xian-Rong Song et al.;《Tetrahedron Letters》;20160801;第57卷(第41期);第4519-4524页 * |
Novel and Efficient Access to Flavones under Mild Conditions:Aqueous HI-Mediated Cascade Cyclization/Oxidative Radical Reaction of 2-Propynolphenols;Xian-Rong Song et al.;《European Journal of Organic Chemistry》;20180914;第2018卷(第40期);第5548-5552页 * |
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