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1. 发明申请

US20130053574A1 ASYMMETRIC HYDROGENATION METHOD FOR KETONE COMPOUND 有权
标题翻译：酮类化合物的不对称加氢方法
公开(公告)号：US20130053574A1
公开(公告)日：2013-02-28
申请号：US13447632
申请日：2012-04-16
申请人： Wanbin Zhang , Delong Liu , Hui Guo , Yangang Liu
发明人： Wanbin Zhang , Delong Liu , Hui Guo , Yangang Liu
IPC分类号： C07C29/145 , C07C213/00 , C07D213/30 , C07C41/26
CPC分类号： C07C29/145 , C07B53/00 , C07B2200/07 , C07C37/002 , C07C41/26 , C07C213/00 , C07C2102/08 , C07C2102/10 , C07C2602/08 , C07C2602/10 , C07C33/22 , C07C33/20 , C07C33/46 , C07C43/23 , C07C39/11 , C07C33/24 , C07C33/18 , C07C35/36 , C07C35/32 , C07C215/68
摘要： The invention relates to an asymmetric hydrogenation method for ketone compounds, comprising the step of: under hydrogen atmosphere, in the presence of an in situ catalyst derived from a chiral ligand and a ruthenium salt, adding a ketone compound and a base into a second solvent to carry out an asymmetric hydrogenation for the ketone compound. The invention can obtain a conversion of 100% and a highest asymmetric inducement effect of 99.7% for the ketone compound. The invention has the advantages including simple procedure, high conversion and selectivity, good atom economy and good prospect of industrial application.
摘要翻译：本发明涉及酮化合物的不对称氢化方法，包括以下步骤：在氢气氛下，在衍生自手性配体和钌盐的原位催化剂存在下，将酮化合物和碱加入到第二溶剂中对酮化合物进行不对称氢化。本发明可以获得酮化合物的100％转化率和99.7％的最高不对称诱导效果。本发明具有工艺简单，转化率高，选择性好，原子经济性好，工业应用前景好的优点。

2. 发明授权

US08962852B2 Asymmetric hydrogenation method for ketone compound 有权
标题翻译：酮类化合物的不对称加氢方法
公开(公告)号：US08962852B2
公开(公告)日：2015-02-24
申请号：US13447632
申请日：2012-04-16
申请人： Wanbin Zhang , Delong Liu , Hui Guo , Yangang Liu
发明人： Wanbin Zhang , Delong Liu , Hui Guo , Yangang Liu
IPC分类号： C07F15/00 , C07C29/145 , C07C37/00 , C07C41/26 , C07C213/00 , C07B53/00
CPC分类号： C07C29/145 , C07B53/00 , C07B2200/07 , C07C37/002 , C07C41/26 , C07C213/00 , C07C2102/08 , C07C2102/10 , C07C2602/08 , C07C2602/10 , C07C33/22 , C07C33/20 , C07C33/46 , C07C43/23 , C07C39/11 , C07C33/24 , C07C33/18 , C07C35/36 , C07C35/32 , C07C215/68
摘要： The invention relates to an asymmetric hydrogenation method for ketone compounds, comprising the step of: under hydrogen atmosphere, in the presence of an in situ catalyst derived from a chiral ligand and a ruthenium salt, adding a ketone compound and a base into a second solvent to carry out an asymmetric hydrogenation for the ketone compound. The invention can obtain a conversion of 100% and a highest asymmetric inducement effect of 99.7% for the ketone compound. The invention has the advantages including simple procedure, high conversion and selectivity, good atom economy and good prospect of industrial application.
摘要翻译：本发明涉及酮化合物的不对称氢化方法，包括以下步骤：在氢气氛下，在衍生自手性配体和钌盐的原位催化剂存在下，将酮化合物和碱加入到第二溶剂中对酮化合物进行不对称氢化。本发明可以获得酮化合物的100％转化率和99.7％的最高不对称诱导效果。本发明具有工艺简单，转化率高，选择性好，原子经济性好，工业应用前景好的优点。

3. 发明申请

US20110160474A1 C2-SYMMETRICAL RUTHENOCENE DIPHOSPHINE LIGANDS ONLY WITH SURFACE CHIRALITY AND THEIR MANUFACTURE 失效
标题翻译： C2-对称二硫代磷酸酯配体仅具有表面光洁度及其制造
公开(公告)号：US20110160474A1
公开(公告)日：2011-06-30
申请号：US12303767
申请日：2007-06-08
申请人： Wanbin Zhang , Fang Xie , Delong Liu , Li Luo , Genghong Hua , Jian Shang
发明人： Wanbin Zhang , Fang Xie , Delong Liu , Li Luo , Genghong Hua , Jian Shang
IPC分类号： C07F17/02
CPC分类号： C07F17/02 , B01J31/2295 , B01J31/24 , B01J31/2409 , B01J2531/0205 , B01J2531/0263 , B01J2531/821
摘要： The invention affords C2-symmetrical ruthenocene diphosphine ligands with surface chirality and their manufacture. The present invention uses (S)—(S)-1,1′-2(diphenylphosphino)-2,2′-2[(S)-4-isopropyloxazolinyl]ruthenocene as raw material and the product is prepared through two or three steps of reaction. At the action of trifluoroacetic acid, (S)—(S)-1,1′-2(diphenylphosphino)-2,2′-2[(S)-4-isopropyloxazolinyl]ruthenocene first removes oxazoline and gets ester amides compound which then carries out ester exchange or reduction alkylation and gets the product of ruthenocene diphosphine ligand with surface chirality. The ligands prepared with the structure as follows from the invention can be used in all kinds of metallic catalysis asymmetric reaction and has good reaction activity and stereoselectivity, wherein R is methyl or ethyl, R1 is linear or branched alkyl, cycloalkyl, alkoxy, aryl, aralkyl and alkyl amino.
摘要翻译：本发明提供具有表面手性及其制造的C2对称的二茂铁二膦配体。本发明使用（S） - （S）-1,1'-2（二苯基膦基）-2,2'-2 [（S）-4-异丙唑恶唑啉基] rut烯为原料，通过2或3 反应步骤。在三氟乙酸的作用下，（S） - （S）-1,1'-2（二苯基膦基）-2,2'-2 [（S）-4-异丙基恶唑啉基] rut hen ene首先除去恶唑啉并得到酯酰胺化合物，然后进行酯交换或还原烷基化，得到具有表面手性的钌基二膦配体的产物。由本发明制备的具有如下结构的配位体可用于各种金属催化不对称反应，具有良好的反应活性和立体选择性，其中R为甲基或乙基，R 1为直链或支链烷基，环烷基，烷氧基，芳基，芳烷基和烷基氨基。

4. 发明授权

US08507705B2 C2-symmetrical ruthenocene diphosphine ligands only with surface chirality and their manufacture 失效
标题翻译： C2对称的二茂铁二膦配体仅具有表面手性及其制造
公开(公告)号：US08507705B2
公开(公告)日：2013-08-13
申请号：US12303767
申请日：2007-06-08
申请人： Wanbin Zhang , Fang Xie , Delong Liu , Li Luo , Genghong Hua , Jian Shang
发明人： Wanbin Zhang , Fang Xie , Delong Liu , Li Luo , Genghong Hua , Jian Shang
IPC分类号： C07F15/00
CPC分类号： C07F17/02 , B01J31/2295 , B01J31/24 , B01J31/2409 , B01J2531/0205 , B01J2531/0263 , B01J2531/821
摘要： The invention affords C2-symmetrical ruthenocene diphosphine ligands with surface chirality and their manufacture. The present invention uses (S)-(S)-1,1′-2(diphenylphosphino)-2,2′-2[(S)-4-isopropyloxazolinyl] ruthenocene as raw material and the product is prepared through two or three steps of reaction. At the action of trifluoroacetic acid, (S)-(S)-1,1′-2(diphenylphosphino)-2,2′-2[(S)-4-isopropyloxazolinyl] ruthenocene first removes oxazoline and gets ester amides compound which then carries out ester exchange or reduction alkylation and gets the product of ruthenocene diphosphine ligand with surface chirality. The ligands prepared with the structure as follows from the invention can be used in all kinds of metallic catalysis asymmetric reaction and has good reaction activity and stereoselectivity, wherein R is methyl or ethyl, R1 is linear or branched alkyl, cycloalkyl, alkoxy, aryl, aralkyl and alkyl amino.
摘要翻译：本发明提供具有表面手性及其制造的C2对称的二茂铁二膦配体。本发明使用（S） - （S）-1,1'-2（二苯基膦基）-2,2'-2 [（S）-4-异丙唑恶唑啉基] rut烯为原料，通过2或3 反应步骤。在三氟乙酸的作用下，（S） - （S）-1,1'-2（二苯基膦基）-2,2'-2 [（S）-4-异丙基恶唑啉基] rut hen ene首先除去恶唑啉并得到酯酰胺化合物，然后进行酯交换或还原烷基化，得到具有表面手性的钌基二膦配体的产物。由本发明制备的具有如下结构的配位体可用于各种金属催化不对称反应，具有良好的反应活性和立体选择性，其中R为甲基或乙基，R 1为直链或支链烷基，环烷基，烷氧基，芳基，芳烷基和烷基氨基。

5. 发明申请

US20100217040A1 2, 2', 6, 6'- TETRASUBSTITUTED AMINOPHOSPHINE LIGAND AND ITS SYNTHESIS METHOD 有权
标题翻译： 2，2'，6,6'-四唑基氨基磷酰胺配体及其合成方法
公开(公告)号：US20100217040A1
公开(公告)日：2010-08-26
申请号：US12377000
申请日：2007-08-10
申请人： Wanbin Zhang , Fang Xie , Fang Fang
发明人： Wanbin Zhang , Fang Xie , Fang Fang
IPC分类号： C07F9/50
CPC分类号： C07F9/46
摘要： The present invention relates to a 2,2′,6,6′-tetrasubstituted aminophosphine ligand and its synthesis method. The structure of the ligand is shown as below. Its synthesis method comprises: Step (1) coupling 2,6-dinitrochlorobenzene as the starting material to obtain 2,2′,6,6′-tetranitrobiphenyl; Step (2): hydrogenating the 2,2′,6,6′-tetranitrobiphenyl with Pd/C to obtain 2,2′,6,6′-tetraminobiphenyl; Step (3): reacting the 2,2′,6,6′-tetraminobiphenyl with a phosphine halide to obtain the 2,2′,6,6′-tetrasubstituted aminophosphine ligand. The ligand of the present invention is an achiral compound, and its preparation method is simple. The ligand can be converted to a chiral bimetallic catalyst with single configuration eventually through introduction of external chirality. Moreover, the ligand can be used in various asymmetric reaction catalyzed by metals with high reactivity and stereoselectivity.
摘要翻译：本发明涉及2,2'，6,6'-四取代氨基膦配体及其合成方法。配体的结构如下所示。其合成方法包括：步骤（1）以2,6-二硝基氯苯为原料，得到2,2'，6,6'-四硝基联苯; 步骤（2）：用Pd / C氢化2,2'，6,6'-四硝基二苯并得到2,2'，6,6'-四氨基联苯; 步骤（3）：使2,2'，6,6'-四磺酰联苯与卤化膦反应，得到2,2'，6,6'-四取代氨基膦配体。本发明的配体是非手性化合物，其制备方法简单。最终可以通过引入外部手性将配体转化为具有单一配置的手性双金属催化剂。此外，配体可用于由具有高反应性和立体选择性的金属催化的各种不对称反应中。

6. 发明申请

US20090156829A1 5,5'- POSITION LINKED 1,1'- BIPHENYL AXIAL CHIRAL LIGAND AND METHOD FOR PREPARING THE SAME 失效
标题翻译： 5,5'-位置连接1,1'-二苯乙烯轴向配对配体及其制备方法
公开(公告)号：US20090156829A1
公开(公告)日：2009-06-18
申请号：US12159440
申请日：2006-12-29
申请人： Wanbin Zhang , Yongjian Zhang , Feijun Wang
发明人： Wanbin Zhang , Yongjian Zhang , Feijun Wang
IPC分类号： C07D413/10
CPC分类号： C07D263/12
摘要： The present invention relates to a 5,5′-position linked 1,1′-biphenyl axis chiral ligand in chemical industry field. The present invention incorporates both the central chirality of oxazoline and the axial chirality of diphenyls. Such ligand can be used in various asymmetric reactions catalyzed by metal with high reactivity and stereoselectivity, and thus represents a good application outlook.The ligand of the present invention has the formula of: wherein: n=5, 6, 7, 8, 9, 10, 11 or 12; R1=hydrogen, alkyl, substituted or unsubstituted aryl, substituted or unsubstituted benzyl; R2=hydrogen, alkyl, substituted or unsubstituted aryl, substituted or unsubstituted benzyl; R3=hydrogen, alkyl, substituted or unsubstituted aryl, substituted or unsubstituted benzyl; R4=hydrogen, alkyl, substituted or unsubstituted aryl, substituted or unsubstituted benzyl.
摘要翻译：本发明涉及化学工业领域中5,5'-位连接的1,1'-联苯轴线手性配体。本发明既包括恶唑啉的中心手性和二苯基的轴向手性。这种配体可用于具有高反应性和立体选择性的金属催化的各种不对称反应中，因此代表了良好的应用前景。本发明的配体具有下式：其中：n = 5,6,7,8,9,10,11或12; R1 =氢，烷基，取代或未取代的芳基，取代或未取代的苄基; R2 =氢，烷基，取代或未取代的芳基，取代或未取代的苄基; R3 =氢，烷基，取代或未取代的芳基，取代或未取代的苄基; R4 =氢，烷基，取代或未取代的芳基，取代或未取代的苄基。

7. 发明授权

US07767825B2 2,2′,6,6′-tetraoxazolinyl biphenyl ligand and method for preparing the same 失效
标题翻译： 2,2'，6,6'-四恶唑啉基联苯基配体及其制备方法
公开(公告)号：US07767825B2
公开(公告)日：2010-08-03
申请号：US12159322
申请日：2006-12-29
申请人： Wanbin Zhang , Yongjian Zhang , Feijun Wang
发明人： Wanbin Zhang , Yongjian Zhang , Feijun Wang
IPC分类号： C07D263/08
CPC分类号： C07D263/14
摘要： The present invention relates to a method for preparing 2,2′,6,6′-tetraoxazolinyl biphenyl ligand in chemical industry field. In the present invention, compound (III) is reacted with an activator that can activate the hydroxyl group selected from the group consisting of alkyl halosulfonium compound, aryl halosulfonium compound, phosphoryl chloride, phosphorus pentachloride, thionyl chloride and triphenyl phosphine, in the presence of alkali(s), to give the target product (IV), 2,2′,6,6′-tetraoxazolinyl biphenyl ligand. The ligand of the present invention can be used in various asymmetric reactions catalyzed by metals, with high reactivity and stereoselectivity, and thus represents a good application outlook. The 2,2′,6,6′-tetraoxazolinyl biphenyl ligand has the formula of: wherein, R1=hydrogen, alkyl, substituted or unsubstituted aryl, substituted or unsubstituted benzyl; R2=hydrogen, alkyl, substituted or unsubstituted aryl, substituted or unsubstituted benzyl; R3=hydrogen, alkyl, substituted or unsubstituted aryl, substituted or unsubstituted benzyl; R4=hydrogen, alkyl, substituted or unsubstituted aryl, substituted or unsubstituted benzyl.
摘要翻译：本发明涉及化学工业领域中2,2'，6,6'-四恶唑啉基联苯配体的制备方法。在本发明中，化合物（III）与可活化选自烷基卤锍化合物，芳基卤锍化合物，磷酰氯，五氯化磷，亚硫酰氯和三苯基膦的羟基的活化剂在存在下反应得到目标产物（IV），2,2'，6,6'-四恶唑啉基联苯基配体。本发明的配体可用于金属催化的各种不对称反应中，具有高反应性和立体选择性，因此代表了良好的应用前景。 2,2'，6,6'-四恶唑啉基联苯配体具有下式：其中，R1 =氢，烷基，取代或未取代的芳基，取代或未取代的苄基; R2 =氢，烷基，取代或未取代的芳基，取代或未取代的苄基; R3 =氢，烷基，取代或未取代的芳基，取代或未取代的苄基; R4 =氢，烷基，取代或未取代的芳基，取代或未取代的苄基。

8. 发明授权

US08729303B2 2,2′,6,6′-tetrasubstituted aminophosphine ligand and its synthesis method 有权
标题翻译： 2,2'，6,6'-四取代氨基膦配体及其合成方法
公开(公告)号：US08729303B2
公开(公告)日：2014-05-20
申请号：US12377000
申请日：2007-08-10
申请人： Wanbin Zhang , Fang Xie , Fang Fang
发明人： Wanbin Zhang , Fang Xie , Fang Fang
IPC分类号： C07F9/02
CPC分类号： C07F9/46
摘要： The present invention relates to a 2,2′,6,6′-tetrasubstituted aminophosphine ligand and its synthesis method. The structure of the ligand is shown as below. Its synthesis method comprises: Step (1) coupling 2,6-dinitrochlorobenzene as the starting material to obtain 2,2′,6,6′-tetranitrobiphenyl; Step (2): hydrogenating the 2,2′,6,6′-tetranitrobiphenyl with Pd/C to obtain 2,2′,6,6′-tetraminobiphenyl; Step (3): reacting the 2,2′,6,6′-tetraminobiphenyl with a phosphine halide to obtain the 2,2′,6,6′-tetrasubstituted aminophosphine ligand. The ligand of the present invention is an achiral compound, and its preparation method is simple. The ligand can be converted to a chiral bimetallic catalyst with single configuration eventually through introduction of external chirality. Moreover, the ligand can be used in various asymmetric reaction catalyzed by metals with high reactivity and stereoselectivity.
摘要翻译：本发明涉及2,2'，6,6'-四取代氨基膦配体及其合成方法。配体的结构如下所示。其合成方法包括：步骤（1）以2,6-二硝基氯苯为原料，得到2,2'，6,6'-四硝基联苯; 步骤（2）：用Pd / C氢化2,2'，6,6'-四硝基二苯并得到2,2'，6,6'-四氨基联苯; 步骤（3）：使2,2'，6,6'-四磺酰联苯与卤化膦反应，得到2,2'，6,6'-四取代氨基膦配体。本发明的配体是非手性化合物，其制备方法简单。最终可以通过引入外部手性将配体转化为具有单一配置的手性双金属催化剂。此外，配体可用于由具有高反应性和立体选择性的金属催化的各种不对称反应中。

9. 发明授权

US07754891B2 5,5′-Position linked 1,1′-biphenyl axial chiral ligand and method for preparing the same 失效
标题翻译： 5,5'-位连接的1,1'-联苯轴向手性配体及其制备方法
公开(公告)号：US07754891B2
公开(公告)日：2010-07-13
申请号：US12159440
申请日：2006-12-29
申请人： Wanbin Zhang , Yongjian Zhang , Feijun Wang
发明人： Wanbin Zhang , Yongjian Zhang , Feijun Wang
IPC分类号： C07D413/10
CPC分类号： C07D263/12
摘要： The present invention relates to a 5,5′-position linked 1,1′-biphenyl axis chiral ligand in chemical industry field. The present invention incorporates both the central chirality of oxazoline and the axial chirality of diphenyls. Such ligand can be used in various asymmetric reactions catalyzed by metal with high reactivity and stereoselectivity, and thus represents a good application outlook. The ligand of the present invention has the formula of: wherein: n=5, 6, 7, 8, 9, 10, 11 or 12; R1=hydrogen, alkyl, substituted or unsubstituted aryl, substituted or unsubstituted benzyl; R2=hydrogen, alkyl, substituted or unsubstituted aryl, substituted or unsubstituted benzyl; R3=hydrogen, alkyl, substituted or unsubstituted aryl, substituted or unsubstituted benzyl; R4=hydrogen, alkyl, substituted or unsubstituted aryl, substituted or unsubstituted benzyl.
摘要翻译：本发明涉及化学工业领域中5,5'-位连接的1,1'-联苯轴线手性配体。本发明既包括恶唑啉的中心手性和二苯基的轴向手性。这种配体可用于具有高反应性和立体选择性的金属催化的各种不对称反应中，因此代表了良好的应用前景。本发明的配体具有下式：其中：n = 5,6,7,8,9,10,11或12; R1 =氢，烷基，取代或未取代的芳基，取代或未取代的苄基; R2 =氢，烷基，取代或未取代的芳基，取代或未取代的苄基; R3 =氢，烷基，取代或未取代的芳基，取代或未取代的苄基; R4 =氢，烷基，取代或未取代的芳基，取代或未取代的苄基。

10. 发明申请

US20090043104A1 2,2',6,6' - TETRAOXAZOLINYL BIPHENYL LIGAND AND METHOD FOR PREPARING THE SAME 失效
标题翻译： 2,2'，6,6' - 四羟甲基苯乙烯联苯系列及其制备方法
公开(公告)号：US20090043104A1
公开(公告)日：2009-02-12
申请号：US12159322
申请日：2006-12-29
申请人： Wanbin Zhang , Yongjian Zhang , Feijun Wang
发明人： Wanbin Zhang , Yongjian Zhang , Feijun Wang
IPC分类号： C07D413/14
CPC分类号： C07D263/14
摘要： The present invention relates to a method for preparing 2,2′,6,6′-tetraoxazolinyl biphenyl ligand in chemical industry field. In the present invention, compound (III) is reacted with an activator that can activate the hydroxyl group selected from the group consisting of alkyl halosulfonium compound, aryl halosulfonium compound, phosphoryl chloride, phosphorus pentachloride, thionyl chloride and triphenyl phosphine, in the presence of alkali(s), to give the target product (IV), 2,2′,6,6′-tetraoxazolinyl biphenyl ligand. The ligand of the present invention can be used in various asymmetric reactions catalyzed by metals, with high reactivity and stereoselectivity, and thus represents a good application outlook. The 2,2′,6,6′-tetraoxazolinyl biphenyl ligand has the formula of: wherein, R1=hydrogen, alkyl, substituted or unsubstituted aryl, substituted or unsubstituted benzyl; R2=hydrogen, alkyl, substituted or unsubstituted aryl, substituted or unsubstituted benzyl; R3=hydrogen, alkyl, substituted or unsubstituted aryl, substituted or unsubstituted benzyl; R4=hydrogen, alkyl, substituted or unsubstituted aryl, substituted or unsubstituted benzyl.
摘要翻译：本发明涉及化学工业领域中2,2'，6,6'-四恶唑啉基联苯配体的制备方法。在本发明中，化合物（III）与可活化选自烷基卤锍化合物，芳基卤锍化合物，磷酰氯，五氯化磷，亚硫酰氯和三苯基膦的羟基的活化剂在存在下反应得到目标产物（IV），2,2'，6,6'-四恶唑啉基联苯基配体。本发明的配体可用于金属催化的各种不对称反应中，具有高反应性和立体选择性，因此代表了良好的应用前景。 2,2'，6,6'-四恶唑啉基联苯配体具有下式：其中，R1 =氢，烷基，取代或未取代的芳基，取代或未取代的苄基; R2 =氢，烷基，取代或未取代的芳基，取代或未取代的苄基; R3 =氢，烷基，取代或未取代的芳基，取代或未取代的苄基; R4 =氢，烷基，取代或未取代的芳基，取代或未取代的苄基。

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