N-芳基-N’-（4，12-取代[2.2]环仿基）咪唑啉盐的合成研究
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摘要
在过去的二十年间,对于具有光学纯度的化合物的合成已经成为有机合成中最重要的领域之一。在已知的一些制备具有光学活性化合物的方法中,不对称催化扮演着重要的角色,并且受关注度越来越高。环仿的一个显著特点是具有面不对称性。在环仿上引入磷、氮、氧、硫等杂原子而制得的手性配体,与过渡金属形成配合物之后,取得了良好的催化效果。手性环仿引入含氮杂环卡宾后,将得到一类新型配体。这类新的手性配体将表现出既不同于环仿又不同于含氮杂环卡宾的特殊性质。所以,对于含有手性环仿的含氮杂环卡宾配体的研究对于发展不对称催化剂和不对称催化反应有着重大而深远的意义。
本论文的实验工作分为九部分,主要内容如下:
一、[2.2]环仿的合成
在强碱环境下,氯化对甲基苄基(?)甲铵中的氯被羟基取代,而后加热下,发生两分子聚合生成[2.2]环仿。
二、4,12-二溴[2.2]环仿的合成
以铁为催化剂,[2.2]环仿在(?)氯甲烷中与溴反应,生成4,16-二溴[2.2]环仿。后者在正十二烷中216℃下转位生成4,12-二溴[2.2]环仿。
三、4-二苯甲酮亚胺-12-溴[2.2]环仿的合成
4,12-二溴[2.2]环仿在催化剂Pd DPPF和强碱叔丁醇钠作用下,与二苯甲酮亚胺发生偶联,得到4-二苯甲酮亚胺-12-溴[2.2]环仿。
四、4-氨基-12-溴[2.2]环仿的合成及拆分
在THF溶液中用浓盐酸水解亚胺生成胺的盐酸盐,再用NaOH碱化为胺,经左旋樟脑磺酸拆分得((?))-4-氨基-12-溴[2.2]环仿和(+)-4-氨基-12-溴[2.2]环仿。
五、Rp-(+)-4-氨基-12-邻甲氧基苯基-[2.2]环仿的合成
通过Suzuki反应,使(-)-4-氨基-12-溴[2.2]环仿与邻甲氧基苯硼酸反应制得。
六、Rp-(+)-N,N'-双(12-邻羟基苯基-4-[2.2]环仿基)乙(?)胺的合成
将Rp-(+)-4-氨基-12-邻甲氧基苯基-[2.2]环仿与乙(?)醛缩合生成乙(?)醛(?)亚胺。在酸性条件下被硼氢化钠还原成Rp-(+)-N,N'-双(12-邻甲氧基苯基-4-[2.2]环仿基)乙二胺,后者在乙酸里被氢溴酸脱甲基得到Rp-(+)-N,N'-双(12-邻羟基苯基-4-[2.2]环仿基)乙二胺。
七、Rp-(-)-N-Ar-N'-(12-溴-4-[2.2]环仿基)乙二胺的合成
芳胺与过量的草酰氯反应生成单酰胺化的草酰氯,后与(-)-4-氨基-12-溴[2.2]环仿反应生成Rp-(-)-N-Ar-N'(12-溴-4-[2.2]环仿基)乙(?)酰二胺。然后被硼烷还原成Rp-(-)-N-Ar-N'(12-溴4-[2.2]环仿基)乙(?)胺。
八、Rp-(+)-N Ar-N'(12-R 4-[2.2]环仿基)乙(?)胺的合成
通过Suzuki反应,Rp-(-)-N-Ar-N'-(12-溴-4-[2.2]环仿基)乙二胺与邻甲氧基苯硼酸和α-萘硼酸反应得到。
九、Rp-((?))-N,N'-双(12-邻羟基苯基-4-[2.2]环仿基)咪唑啉氟硼酸盐和Rp-(-)-N-Ar-N'(12-R-4-[2.2]环仿基)咪唑啉氟硼酸盐的合成
上述得到的(?)胺与原甲酸(?)乙酯和氟硼酸铵关环得到其咪唑啉氟硼酸盐。
本论文的创新之处:
1.合成了五种含环仿基的新(?)胺化合物。
2.合成了五种含环仿的新咪唑啉氟硼酸盐。
During the past two decades,the synthesis of enantiomerically pure or enriched compounds has emerged as one of the most important fields in organic synthesis. Several procedures to generate optically active molecules are known,and among these,asymmetric catalysis plays an important role and is a highly active research area.The paracyclophane shows striking characteristic with the planar chirality.By introducing the heteoratom,such as phosphor,nitrogen,oxygen and sulphur into paracyclophane,the paracyclophane-based chiral complexs formed with transitional metals already display good stereoselectivity in catalyzing asymmetric synthesis reaction.A series of novel complexes derived from planar chiral paracyclophane and N-heterocyclic carbene reveal much special character that is different from neither the paracyclophane nor the N-heterocyclic carbene.Thus,the research of these novel complexes will have significant and profound meaning for the development of asymmetric catalyst and asymmetric catalytic reaction.
This paper is consisted of nine parts:
The first part is preparation of[2.2]paracyclophane.Para-methylbenzylammonium chloride reacted with sodium hydroxide at 80-90℃to produce [2.2]paracyclophane.
The second part is preparation of 4,12-dibromo[2.2]paracyclophane. 4,16-dibromo[2.2]paracyclophane was obtained by bromination of[2.2]paracyclophane using iron as catalyst,and a suspension of 4,16-dibromo[2.2]paracyclophane in dodecane was heated at 216℃for 20h to afford 4,12-dibromo[2.2] paracyclophane.
The third part is preparation of 4-benzophenone imino-12-bromo[2.2]paracyclophane. It was obtained by treatment of 4,12-dibromo[2.2]paracyclophane with benzophenone imine,sodium tert-butoxide and Pd-DPPF.
The forth part is preparation and resolution of 4-amino-12-bromo[2.2]paracyclophane. It was hydrolyzed with HCl in THF to furnish exclusively 4-amino12-bromo [2.2]paracyclophane.
The fifth part is preparation of Rp-(+)-4-amino-12-(2-methoxyphenyl) [2.2]paracyclophane.It was obtained by Suzuki cross coupling with 2-methoxyphenyl boronic acid under Pd-DPPF catalysis.
The sixth part is preparation of Rp-(+)-N,N'-bis{12-(2-hydroxyl phenyl)-4-[2.2] paracyclophane} ethylene-1,2-diamine.Rp-(+)-N,N'-bis{12-(2-methoxyl phenyl) -4-[2.2]paracyclophane}glyoxal diimine was obtained by treatment Rp-(+)-4-amino-12-(2-methoxyphenyl)[2.2]paracyclophane with glyoxal,then it was reduced to the diamine with sodium borohydride.Rp-(+)-N,N'-bis{12-(2-hydroxy phenyl)-4-[2.2]paracyclophane}ethylene-1,2-diamine was obtained from Rp-(+)-N,N'-bis{12-(2-methoxyphenyl)-4-[2.2]paracyclophane}ethylene-1,2-diamine by demethanation with HBr in acetic acid at 114℃for 5h.
The seventh part is preparation of Rp-(-)-N-Ar-N'-(12-bromo-4-[2.2]paracyclophane) ethylene-1,2-diamine.Starting from oxalyl chloride and aromatic amines, oxo-arylamino acetyl chlorides were obtained,and then reacted with 4-amino-12bromo [2.2]paracyclophane to produce Rp-(-)-N-Ar-N'-(12-bromo-4-[2.2]paracyclo phanyl)oxamide.Next,the oxamide was reduced by borane to give Rp-(-)-N-Ar-N'-(12-bromo-4-[2.2] paracyclophanyl)ethylene-1,2-diamine.
The eighth part is preparation of Rp-(+)-N-Ar-N'-(12-R-4-[2.2]paracyclophanyl) ethylene-1,2-diamine.Under Pd-DPPF catalysis,it was obtained by Suzuki cross coupling with 2-methoxy-phenyl boronic acid,andα-naphthyl boronic acid, respectively.
The ninth part is preparation of the new chiral dicyclophane dihydroimidazolium tetrafluoroborates.They were gained from the diamine,triethyl orthoformate and ammonium tetrafluoroborate.
The innovation of this thesis is as follows:
1.Five novel diamine compounds were obtained.
2.Five novel dihydroimidazolium tetrafluoroborates were obtained.
本论文的实验工作分为九部分,主要内容如下:
一、[2.2]环仿的合成
在强碱环境下,氯化对甲基苄基(?)甲铵中的氯被羟基取代,而后加热下,发生两分子聚合生成[2.2]环仿。
二、4,12-二溴[2.2]环仿的合成
以铁为催化剂,[2.2]环仿在(?)氯甲烷中与溴反应,生成4,16-二溴[2.2]环仿。后者在正十二烷中216℃下转位生成4,12-二溴[2.2]环仿。
三、4-二苯甲酮亚胺-12-溴[2.2]环仿的合成
4,12-二溴[2.2]环仿在催化剂Pd DPPF和强碱叔丁醇钠作用下,与二苯甲酮亚胺发生偶联,得到4-二苯甲酮亚胺-12-溴[2.2]环仿。
四、4-氨基-12-溴[2.2]环仿的合成及拆分
在THF溶液中用浓盐酸水解亚胺生成胺的盐酸盐,再用NaOH碱化为胺,经左旋樟脑磺酸拆分得((?))-4-氨基-12-溴[2.2]环仿和(+)-4-氨基-12-溴[2.2]环仿。
五、Rp-(+)-4-氨基-12-邻甲氧基苯基-[2.2]环仿的合成
通过Suzuki反应,使(-)-4-氨基-12-溴[2.2]环仿与邻甲氧基苯硼酸反应制得。
六、Rp-(+)-N,N'-双(12-邻羟基苯基-4-[2.2]环仿基)乙(?)胺的合成
将Rp-(+)-4-氨基-12-邻甲氧基苯基-[2.2]环仿与乙(?)醛缩合生成乙(?)醛(?)亚胺。在酸性条件下被硼氢化钠还原成Rp-(+)-N,N'-双(12-邻甲氧基苯基-4-[2.2]环仿基)乙二胺,后者在乙酸里被氢溴酸脱甲基得到Rp-(+)-N,N'-双(12-邻羟基苯基-4-[2.2]环仿基)乙二胺。
七、Rp-(-)-N-Ar-N'-(12-溴-4-[2.2]环仿基)乙二胺的合成
芳胺与过量的草酰氯反应生成单酰胺化的草酰氯,后与(-)-4-氨基-12-溴[2.2]环仿反应生成Rp-(-)-N-Ar-N'(12-溴-4-[2.2]环仿基)乙(?)酰二胺。然后被硼烷还原成Rp-(-)-N-Ar-N'(12-溴4-[2.2]环仿基)乙(?)胺。
八、Rp-(+)-N Ar-N'(12-R 4-[2.2]环仿基)乙(?)胺的合成
通过Suzuki反应,Rp-(-)-N-Ar-N'-(12-溴-4-[2.2]环仿基)乙二胺与邻甲氧基苯硼酸和α-萘硼酸反应得到。
九、Rp-((?))-N,N'-双(12-邻羟基苯基-4-[2.2]环仿基)咪唑啉氟硼酸盐和Rp-(-)-N-Ar-N'(12-R-4-[2.2]环仿基)咪唑啉氟硼酸盐的合成
上述得到的(?)胺与原甲酸(?)乙酯和氟硼酸铵关环得到其咪唑啉氟硼酸盐。
本论文的创新之处:
1.合成了五种含环仿基的新(?)胺化合物。
2.合成了五种含环仿的新咪唑啉氟硼酸盐。
During the past two decades,the synthesis of enantiomerically pure or enriched compounds has emerged as one of the most important fields in organic synthesis. Several procedures to generate optically active molecules are known,and among these,asymmetric catalysis plays an important role and is a highly active research area.The paracyclophane shows striking characteristic with the planar chirality.By introducing the heteoratom,such as phosphor,nitrogen,oxygen and sulphur into paracyclophane,the paracyclophane-based chiral complexs formed with transitional metals already display good stereoselectivity in catalyzing asymmetric synthesis reaction.A series of novel complexes derived from planar chiral paracyclophane and N-heterocyclic carbene reveal much special character that is different from neither the paracyclophane nor the N-heterocyclic carbene.Thus,the research of these novel complexes will have significant and profound meaning for the development of asymmetric catalyst and asymmetric catalytic reaction.
This paper is consisted of nine parts:
The first part is preparation of[2.2]paracyclophane.Para-methylbenzylammonium chloride reacted with sodium hydroxide at 80-90℃to produce [2.2]paracyclophane.
The second part is preparation of 4,12-dibromo[2.2]paracyclophane. 4,16-dibromo[2.2]paracyclophane was obtained by bromination of[2.2]paracyclophane using iron as catalyst,and a suspension of 4,16-dibromo[2.2]paracyclophane in dodecane was heated at 216℃for 20h to afford 4,12-dibromo[2.2] paracyclophane.
The third part is preparation of 4-benzophenone imino-12-bromo[2.2]paracyclophane. It was obtained by treatment of 4,12-dibromo[2.2]paracyclophane with benzophenone imine,sodium tert-butoxide and Pd-DPPF.
The forth part is preparation and resolution of 4-amino-12-bromo[2.2]paracyclophane. It was hydrolyzed with HCl in THF to furnish exclusively 4-amino12-bromo [2.2]paracyclophane.
The fifth part is preparation of Rp-(+)-4-amino-12-(2-methoxyphenyl) [2.2]paracyclophane.It was obtained by Suzuki cross coupling with 2-methoxyphenyl boronic acid under Pd-DPPF catalysis.
The sixth part is preparation of Rp-(+)-N,N'-bis{12-(2-hydroxyl phenyl)-4-[2.2] paracyclophane} ethylene-1,2-diamine.Rp-(+)-N,N'-bis{12-(2-methoxyl phenyl) -4-[2.2]paracyclophane}glyoxal diimine was obtained by treatment Rp-(+)-4-amino-12-(2-methoxyphenyl)[2.2]paracyclophane with glyoxal,then it was reduced to the diamine with sodium borohydride.Rp-(+)-N,N'-bis{12-(2-hydroxy phenyl)-4-[2.2]paracyclophane}ethylene-1,2-diamine was obtained from Rp-(+)-N,N'-bis{12-(2-methoxyphenyl)-4-[2.2]paracyclophane}ethylene-1,2-diamine by demethanation with HBr in acetic acid at 114℃for 5h.
The seventh part is preparation of Rp-(-)-N-Ar-N'-(12-bromo-4-[2.2]paracyclophane) ethylene-1,2-diamine.Starting from oxalyl chloride and aromatic amines, oxo-arylamino acetyl chlorides were obtained,and then reacted with 4-amino-12bromo [2.2]paracyclophane to produce Rp-(-)-N-Ar-N'-(12-bromo-4-[2.2]paracyclo phanyl)oxamide.Next,the oxamide was reduced by borane to give Rp-(-)-N-Ar-N'-(12-bromo-4-[2.2] paracyclophanyl)ethylene-1,2-diamine.
The eighth part is preparation of Rp-(+)-N-Ar-N'-(12-R-4-[2.2]paracyclophanyl) ethylene-1,2-diamine.Under Pd-DPPF catalysis,it was obtained by Suzuki cross coupling with 2-methoxy-phenyl boronic acid,andα-naphthyl boronic acid, respectively.
The ninth part is preparation of the new chiral dicyclophane dihydroimidazolium tetrafluoroborates.They were gained from the diamine,triethyl orthoformate and ammonium tetrafluoroborate.
The innovation of this thesis is as follows:
1.Five novel diamine compounds were obtained.
2.Five novel dihydroimidazolium tetrafluoroborates were obtained.
引文
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