CN103819400B - 一种多组分反应合成具有不对称结构1.4-二氢吡啶及其衍生物的方法 - Google Patents

一种多组分反应合成具有不对称结构1.4-二氢吡啶及其衍生物的方法 Download PDF

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CN103819400B
CN103819400B CN201310418468.8A CN201310418468A CN103819400B CN 103819400 B CN103819400 B CN 103819400B CN 201310418468 A CN201310418468 A CN 201310418468A CN 103819400 B CN103819400 B CN 103819400B
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dihydropyridine
compound
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CN103819400A (zh
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万结平
周友谊
刘云云
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Jiangxi Normal University
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Jiangxi Normal University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms

Abstract

一种多组分反应合成具有不对称结构1.4-二氢吡啶及其衍生物的方法，化学式为C30H26O2NCl，褐色固体，熔点为196-197oC。本发明的优点是：1、具有手性中心；2、该化合物为不对称稠环结构，对二氢吡啶化合物的多样性合成进行了拓展；3、合成方法简单，易操作、原料来源充足、生产成本低廉、适合工业化生产。

Description

一种多组分反应合成具有不对称结构1.4-二氢吡啶及其衍生物的方法
技术领域
本发明涉及一种不对称结构的1.4-二氢吡啶化合物的制备方法，尤其涉及一种一种不对称的1.4-二氢吡啶化合物3-苯甲酰基-4-(4-氯苯基)-7,7-二甲基-1-苯基-7,8-二氢喹啉-5(1H,4H,6H)酮及其制备方法。
背景技术
1.4-二氢吡啶类化合物是吡啶的部分还原衍生物。这类化合物结构骨架广泛存在与天然产物、药物以及具有生物活性的分子中。典型的1,4-二氢吡啶类药物包括溴苯地平，非洛地平钙拮抗剂。同时，文献已报道1.4-二氢吡啶具有抗肿瘤，抗动脉粥样硬化，抗糖尿病，抗血管扩张，抗高血压等生物活性。
发明内容
本发明的目的在于提供一种一种不对称的1.4-二氢吡啶化合物3-苯甲酰基-4-(4-氯苯基)-7,7-二甲基-1-苯基-7,8-二氢喹啉-5(1H,4H,6H)酮及其制备方法，合成方法简单，易操作、原料来源充足、生产成本低廉、绿色环保。
本发明是这样来实现的，一种不对称的1.4-二氢吡啶化合物3-苯甲酰基-4-(4-氯苯基)-7,7-二甲基-1-苯基-7,8-二氢喹啉-5(1H,4H,6H)酮，其特征是化学式为C30H26O2NCl,褐色固体,熔点为196-197oC。
所述的一种不对称的1.4-二氢吡啶化合物3-苯甲酰基-4-(4-氯苯基)-7,7-二甲基-1-苯基-7,8-二氢喹啉-5(1H,4H,6H)酮的制备方法，其特征是方法为具体是将醛、烯胺酮、芳香族烯胺酮按照1:1:1的摩尔比例放入10毫升的圆底烧瓶中，再加入0.5mmol催化剂三甲基氯硅烷和2ml溶剂二甲亚砜，然后恒温在363K反应12小时，反应结束后加水、乙酸乙酯分层，用乙酸乙酯萃取三次，每次10ml，有机相用无水硫酸镁干燥，之后用柱层析分离得到产物。
本发明的技术效果是：本发明的是一个原子经济性的合成具有潜在生物药物功能杂环化合物的方法，该法操作简便，通过多组分反应合成一步实现，具有合成更多样的类似二氢吡啶产物，对发现基于该杂环骨架的先导化合物和药物有重要指导作用。具有手性中心；该化合物为不对称稠环结构，对二氢吡啶化合物的多样性合成进行了拓展；合成方法简单，易操作、原料来源充足、生产成本低廉、适合工业化生产。
附图说明
图1为本发明化合物核磁共振氢谱图。
图2为本发明化合物核磁共振碳谱图。
具体实施方式
将对氯苯甲醛1(0.5mmol)，N-苯基环烯胺酮2(0.5mmol)和二甲氨基烯胺酮3(0.5mmol)按照1:1:1的摩尔比例放入10毫升的圆底烧瓶中，再加入催化剂三甲基氯硅烷(0.5mmol)，溶剂二甲亚砜(2ml)，在90oC反应12小时，反应结束后加水10mL，并加入10mL乙酸乙酯，待体系分层后，分去水相，再用乙酸乙酯萃取2次，每次10ml。合并有机相，并用无水硫酸镁干燥，过79%。本发明具体反应式为
如图1、图２所示，其核磁数据为：
1HNMR(CDCl3,300MHz),δ7.52-7.38(m,8H),7.32(t,2H,J=9.0Hz),7.26-7.22(m,4H),7.05(s,1H),5.45(s,1H),2.21(d,2H,J=3.0Hz),2.08(dd,2H,J1=15.0Hz,J2=12.0Hz),0.98(s,3H),0.90(s,3H);13CNMR(CDCl3,75MHz),δ195.4,194.4,149.0,144.5,142.7,141.5,138.9,131.9,130.9,130.2,129.3,128.9,128.4,128.2,127.4,118.5,114.3,50.4,41.2,34.4,32.6,29.0,27.5。

Claims (2)

1.一种不对称的1,4-二氢吡啶化合物，其特征在于：该化合物为3-苯甲酰基-4-(4-氯苯基)-7,7-二甲基-1-苯基-7,8-二氢喹啉-5(1H,4H,6H)酮，其化学式为C30H26O2NCl，性状为褐色固体，熔点为196-197oC。
2.一种权利要求1所述的一种不对称的1,4-二氢吡啶化合物的制备方法，其特征是方法为具体是将对氯苯甲醛，N-苯基环烯胺酮和二甲氨基烯胺酮按照1:1:1的摩尔比例放入10毫升的圆底烧瓶中，再加入0.5mmol催化剂三甲基氯硅烷和2ml溶剂二甲亚砜，然后恒温在363K反应12小时，反应结束后加水、乙酸乙酯分层，用乙酸乙酯萃取三次，每次10ml，有机相用无水硫酸镁干燥，之后用柱层析分离得到产物。
CN201310418468.8A 2013-09-16 2013-09-16 一种多组分反应合成具有不对称结构1.4-二氢吡啶及其衍生物的方法 Expired - Fee Related CN103819400B (zh)

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