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1. 发明授权

US06727381B2 Process for producing vitamin A ester 有权
标题翻译：生产维生素A酯的方法
公开(公告)号：US06727381B2
公开(公告)日：2004-04-27
申请号：US10039056
申请日：2002-01-03
申请人： Runpu Shen , Shiqing Pi , Bin Xie , Hongjun Huang
发明人： Runpu Shen , Shiqing Pi , Bin Xie , Hongjun Huang
IPC分类号： C07C6702
CPC分类号： C07C403/12 , C07C2601/16 , C07F9/4018
摘要： The invention relates to a process for producing all trans-vitamin A ester (I). According to the present invention, vitamin A ester (I) can simply be synthesized in good yields and high purity by the reaction of phosphonate compound (IV) with aldehyde (II) in an organic solvent in the presence of a base.
摘要翻译：本发明涉及一种生产全部维生素A酯（I）的方法。根据本发明，通过膦酸酯化合物（IV）与醛（II）在有机溶剂中在碱的存在下的反应，可以简单地以高产率和高纯度合成维生素A酯（I）。

2. 发明授权

US09051254B2 Method of preparing 2,6,10-Trimethyl-1,1-dialkoxy-3,5,9-undecatriene used as an intermediate of lycopene 有权
标题翻译：制备用作番茄红素中间体的2,6,10-三甲基-1,1-二烷氧基-3,5,9-十一碳三烯的方法
公开(公告)号：US09051254B2
公开(公告)日：2015-06-09
申请号：US13493971
申请日：2012-06-11
申请人： Pengfei Zhang , Chao Shen , Runpu Shen , Wei Liu , Chunlei Wu
发明人： Pengfei Zhang , Chao Shen , Runpu Shen , Wei Liu , Chunlei Wu
IPC分类号： C07C41/01 , C07C41/48
CPC分类号： C07C41/48 , C07C43/303
摘要： The present invention describes a novel synthetic method for preparing the key intermediate 2,6,10-trimethyl-1,1-dialkoxy-3,5,9-undecatriene of lycopene. An existing synthetic method have some disadvantages that it is very difficult to gain the raw material dialkyl 4-methyl-5,5-diakoxy-1-pentene-1-phosphonate (10) because no effective synthetic method can be adopted, and furthermore the obtained target compound is composed of several cis/trans isomers. This invention relates to a process comprising a condensation step wherein a starting C10-phosphonate is changed to its carbanion completely at a temperature of −40˜30 under an atmosphere of a non-reactive gas in an organic solvent catalyzed by base, and then C4-dialkyl is added to undergo Wittig-Horner condensation. This invention affords all trans C14-acetal and this method is characterized with the advantages of simple procedure, easy access to raw material and low cost, which makes it has the value of industrial application.
摘要翻译：本发明描述了一种制备番茄红素关键中间体2,6,10-三甲基-1,1-二烷氧基-3,5,9-十一碳三烯的新型合成方法。现有的合成方法有一些缺点，因为没有有效的合成方法，难以获得原料的4-甲基-5,5-二烷氧基-1-戊烯-1-膦酸二烷基酯（10），此外，得到的目标化合物由几种顺式/反式异构体组成。本发明涉及一种包括缩合步骤的方法，其中起始C10-膦酸酯在-40〜30℃的温度下在非反应性气体的气氛中在由碱催化的有机溶剂中完全变成其碳负离子，然后将C4 加入二烷基以进行Wittig-Horner冷凝。本发明提供全反式C14-缩醛，该方法的特点是操作简单，易于获得原料，成本低廉，具有工业应用价值。

3. 发明申请

US20120330048A1 Lycopene Intermediate 1, 3, 6, 10-Tetra-Double Bond Pentadec-Carbon Phosphonate as well as Preparation Method and Use Thereof 有权
标题翻译：番茄红素中间体1,3,6,10-四 - 双键十五碳膦酸酯及其制备方法和用途
公开(公告)号：US20120330048A1
公开(公告)日：2012-12-27
申请号：US13583635
申请日：2011-03-09
申请人： Xuejun Lao , Runpu Shen , Weidong Ye , Xiaohua Song , Luo Liu , Chunlei Wu , Yibin Wu , Liujiang Hu
发明人： Xuejun Lao , Runpu Shen , Weidong Ye , Xiaohua Song , Luo Liu , Chunlei Wu , Yibin Wu , Liujiang Hu
IPC分类号： C07F9/40
CPC分类号： C07F9/4015
摘要： The invention relates to a novel important lycopene intermediate 3,7, 11-trimethyl-1,3,6,10-tetraene-dodecyl diethyl phosphonate. A current lycopene intermediate 2,4,6,10-tetra-double bond pentadec-carbon phosphonate is difficult to synthesize. The invention provides a novel intermediate, which has the following synthesis steps of: preparing 2,6,10-trimethyl-3,5,9-undecane triene-1-aldehyde from pseudoionone; preparing 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde from the 2,6,10-trimethyl-3, 5,9-undecane triene-1-aldehyde; and subjecting the 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde and tetraethyl methylenediphosphonate to condensation reaction to obtain target product. The invention can generate novel intermediate from raw material pseudoionone only by four reactions, thus the reactions are easy to control and great industrial value are achieved.
摘要翻译：本发明涉及一种新型重要的番茄红素中间体3,7,11-三甲基-1,3,6,10-四烯十二烷基二乙基膦酸酯。目前的番茄红素中间体2,4,6,10-四 - 双十五碳酸膦难以合成。本发明提供了一种新的中间体，其具有以下合成步骤：由假雄酮制备2,6,10-三甲基-3,5,9-十一烷三烯-1-醛; 由2,6,10-三甲基-3,9,9-十一烷三烯-1-醛制备2,6,10-三甲基-2,5,9-十一烷三烯-1-醛; 并使2,6,10-三甲基-2,5,9-十一烷三烯-1-醛和四亚乙基二膦酸四乙酯进行缩合反应，得到目标产物。本发明只能通过四个反应从原料假雄酮生成新的中间体，因此反应易于控制，实现了巨大的工业价值。

4. 发明授权

US08765988B2 Lycopene intermediate 1, 3, 6, 10-tetra-double bond pentadec-carbon phosphonate as well as preparation method and use thereof 有权
标题翻译：番茄红素中间体1,3,6,10-四 - 双十五碳酸膦酸酯及其制备方法和用途
公开(公告)号：US08765988B2
公开(公告)日：2014-07-01
申请号：US13583635
申请日：2011-03-09
申请人： Xuejun Lao , Runpu Shen , Weidong Ye , Xiaohua Song , Luo Liu , Chunlei Wu , Yibin Wu , Liujiang Hu
发明人： Xuejun Lao , Runpu Shen , Weidong Ye , Xiaohua Song , Luo Liu , Chunlei Wu , Yibin Wu , Liujiang Hu
IPC分类号： C07F9/40
CPC分类号： C07F9/4015
摘要： The invention relates to a novel important lycopene intermediate 3,7,11-trimethyl-1,3,6,10-tetraene-dodecyl diethyl phosphonate. A current lycopene intermediate 2,4,6,10-tetra-double bond pentadec-carbon phosphonate is difficult to synthesize. The invention provides a novel intermediate, which has the following synthesis steps of: preparing 2,6,10-trimethyl-3,5,9-undecane triene-1-aldehyde from pseudoionone; preparing 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde from the 2,6,10-trimethyl-3,5,9-undecane triene-1-aldehyde; and subjecting the 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde and tetraethyl methylenediphosphonate to condensation reaction to obtain target product. The invention can generate novel intermediate from raw material pseudoionone only by four reactions, thus the reactions are easy to control and great industrial value are achieved.
摘要翻译：本发明涉及新型重要的番茄红素中间体3,7,11-三甲基-1,3,6,10-四烯十二烷基二乙基膦酸酯。目前的番茄红素中间体2,4,6,10-四 - 双十五碳酸膦难以合成。本发明提供了一种新的中间体，其具有以下合成步骤：由假雄酮制备2,6,10-三甲基-3,5,9-十一烷三烯-1-醛; 由2,6,10-三甲基-3,5,9-十一烷三烯-1-醛制备2,6,10-三甲基-2,5,9-十一烷三烯-1-醛; 并使2,6,10-三甲基-2,5,9-十一烷三烯-1-醛和四亚乙基二膦酸四乙酯进行缩合反应，得到目标产物。本发明只能通过四个反应从原料假雄酮生成新的中间体，因此反应易于控制，实现了巨大的工业价值。

5. 发明授权

US07351854B2 Method of manufacturing 1-chloro-2-methyl-4-acyloxy-2-butene derivatives 有权
标题翻译： 1-氯-2-甲基-4-酰氧基-2-丁烯衍生物的制备方法
公开(公告)号：US07351854B2
公开(公告)日：2008-04-01
申请号：US11749793
申请日：2007-05-17
申请人： Runpu Shen , Guoqi Yu , Weidong Ye , Kui Wang , Xuejun Lao
发明人： Runpu Shen , Guoqi Yu , Weidong Ye , Kui Wang , Xuejun Lao
IPC分类号： C07C67/02
CPC分类号： C07C67/08 , C07C29/66 , C07C67/14 , C07C67/293 , C07C33/423 , C07C69/007 , C07C69/63
摘要： 1-Chloro-2-methyl-4-acyloxy-2-butene derivatives can be synthesized in good yields and high purity starting from isoprene and employing a chlorohydrin formation reaction in a system made of N-chloroisocyanuric acid derivatives and water, followed by esterification and rearrangement of the crude product mixture.
摘要翻译： 1-异-2-甲基-4-酰氧基-2-丁烯衍生物可以从异戊二烯开始以良好的产率和高纯度合成，并且在由N-氯异氰尿酸衍生物和水制成的体系中使用氯代醇形成反应，随后酯化和粗产物混合物的重排。

6. 发明申请

US20070270607A1 METHOD OF MANUFACTURING 1-CHLORO-2-METHYL-4-ACYLOXY-2-BUTENE DERIVATIVES 有权
标题翻译：制备1-氯代-2-甲基-4-亚乙基-2-丁烯衍生物的方法
公开(公告)号：US20070270607A1
公开(公告)日：2007-11-22
申请号：US11749793
申请日：2007-05-17
申请人： Runpu SHEN , Guoqi YU , Weidong YE , Kui WANG , Xuejun LAO
发明人： Runpu SHEN , Guoqi YU , Weidong YE , Kui WANG , Xuejun LAO
IPC分类号： C07C67/02
CPC分类号： C07C67/08 , C07C29/66 , C07C67/14 , C07C67/293 , C07C33/423 , C07C69/007 , C07C69/63
摘要： 1-Chloro-2-methyl-4-acyloxy-2-butene derivatives can be synthesized in good yields and high purity starting from isoprene and employing a chlorohydrin formation reaction in a system made of N-chloroisocyanuric acid derivatives and water, followed by esterification and rearrangement of the crude product mixture.
摘要翻译： 1-异-2-甲基-4-酰氧基-2-丁烯衍生物可以从异戊二烯开始以良好的产率和高纯度合成，并且在由N-氯异氰尿酸衍生物和水制成的体系中使用氯代醇形成反应，随后酯化和粗产物混合物的重排。

7. 发明授权

US08962827B2 Linezolid intermediate and method for synthesizing linezolid 有权
标题翻译：利奈唑胺中间体和合成利奈唑胺的方法
公开(公告)号：US08962827B2
公开(公告)日：2015-02-24
申请号：US14008124
申请日：2012-04-12
申请人： Xiaoyue Jiang , Guofeng Wu , Weidong Ye , Runpu Shen , Xiaohua Song
发明人： Xiaoyue Jiang , Guofeng Wu , Weidong Ye , Runpu Shen , Xiaohua Song
IPC分类号： C07D413/10 , C07C233/18 , C07D263/20 , C07C231/12 , C07D263/24
CPC分类号： C07C233/18 , C07C231/12 , C07D263/20 , C07D263/24 , C07D413/10
摘要： Provided are a linezolid intermediate and the preparation method thereof and a method for synthesizing linezolid. The structure of the intermediate is shown as formula F2, wherein the compound is prepared by a condensation reaction of (S)—N-(3-chloro-2-hydroxy-1-propyl) acetamide and the compound shown in formula F4. In the preparation methods of the compound shown in formula F2 and linezolid, the reaction system is mild, side reactions are few and the product yield is high.
摘要翻译：提供了一种利奈唑胺中间体及其制备方法和合成利奈唑胺的方法。中间体的结构如式F2所示，其中化合物通过（S）-N-（3-氯-2-羟基-1-丙基）乙酰胺与式F4所示的化合物的缩合反应制备。在式F2和利奈唑胺的化合物的制备方法中，反应体系温和，副反应少，产物收率高。

8. 发明申请

US20140024827A1 LINEZOLID INTERMEDIATE AND METHOD FOR SYNTHESIZING LINEZOLID 有权
标题翻译： LINEZOLID中间体和用于合成LINEZOLID的方法
公开(公告)号：US20140024827A1
公开(公告)日：2014-01-23
申请号：US14008124
申请日：2012-04-12
申请人： Xiaoyue Jiang , Guofeng Wu , Weidong Ye , Runpu Shen , Xiaohua Song
发明人： Xiaoyue Jiang , Guofeng Wu , Weidong Ye , Runpu Shen , Xiaohua Song
IPC分类号： C07C233/18 , C07D263/24 , C07C231/12
CPC分类号： C07C233/18 , C07C231/12 , C07D263/20 , C07D263/24 , C07D413/10
摘要： Provided are a linezolid intermediate and the preparation method thereof and a method for synthesizing linezolid. The structure of the intermediate is shown as formula F2, wherein the compound is prepared by a condensation reaction of (S)—N—(3-chloro-2-hydroxy-1-propyl) acetamide and the compound shown in formula F4. In the preparation methods of the compound shown in formula F2 and linezolid, the reaction system is mild, side reactions are few and the product yield is high.
摘要翻译：提供了一种利奈唑胺中间体及其制备方法和合成利奈唑胺的方法。中间体的结构如式F2所示，其中化合物通过（S）-N-（3-氯-2-羟基-1-丙基）乙酰胺与式F4所示的化合物的缩合反应制备。在式F2和利奈唑胺的化合物的制备方法中，反应体系温和，副反应少，产物收率高。

9. 发明申请

US20120316366A1 Method of Preparing 2,6,10-Trimethyl-1,1-Dialkoxy-3,5,9-Undecatriene Used as an Intermediate of Lycopene 有权
标题翻译：制备用作番茄红素中间体的2,6,10-三甲基-1,1-二烷氧基-3,5,9-十一碳三烯的方法
公开(公告)号：US20120316366A1
公开(公告)日：2012-12-13
申请号：US13493971
申请日：2012-06-11
申请人： PENGFEI ZHANG , CHAO SHEN , RUNPU SHEN , WEI LIU , CHUNLEI WU
发明人： PENGFEI ZHANG , CHAO SHEN , RUNPU SHEN , WEI LIU , CHUNLEI WU
IPC分类号： C07C41/01
CPC分类号： C07C41/48 , C07C43/303
摘要： The present invention describes a novel synthetic method for preparing the key intermediate 2,6,10-trimethyl-1,1-dialkoxy-3,5,9-undecatriene of lycopene. An existing synthetic method have some disadvantages that it is very difficult to gain the raw material dialkyl 4-methyl-5,5-diakoxy-1-pentene-1-phosphonate (10) because no effective synthetic method can be adopted, and furthermore the obtained target compound is composed of several cis/trans isomers. This invention relates to a process comprising a condensation step wherein a starting C10-phosphonate is changed to its carbanion completely at a temperature of −40˜30 under an atmosphere of a non-reactive gas in an organic solvent catalyzed by base, and then C4-dialkyl is added to undergo Wittig-Horner condensation. This invention affords all trans C14-acetal and this method is characterized with the advantages of simple procedure, easy access to raw material and low cost, which makes it has the value of industrial application.
摘要翻译：本发明描述了一种制备番茄红素关键中间体2,6,10-三甲基-1,1-二烷氧基-3,5,9-十一碳三烯的新型合成方法。现有的合成方法有一些缺点，因为没有有效的合成方法，难以获得原料的4-甲基-5,5-二烷氧基-1-戊烯-1-膦酸二烷基酯（10），此外，得到的目标化合物由几种顺式/反式异构体组成。本发明涉及一种包括缩合步骤的方法，其中起始C10-膦酸酯在-40〜30℃的温度下在非反应性气体的气氛中在由碱催化的有机溶剂中完全变成其碳负离子，然后将C4 加入二烷基以进行Wittig-Horner冷凝。本发明提供全反式C14-缩醛，该方法的特点是操作简单，易于获得原料，成本低廉，具有工业应用价值。

10. 发明授权

US08697919B2 1-methoxyl-2, 6, 10-trimethyl-1, 3, 5, 9-undec-tetraene, and preparation method and uses thereof 有权
标题翻译： 1-甲氧基-2,6,10-三甲基-1,3,5,9-十一四烯及其制备方法和用途
公开(公告)号：US08697919B2
公开(公告)日：2014-04-15
申请号：US13639852
申请日：2011-04-06
申请人： Xuejun Lao , Runpu Shen , Weidong Ye , Xiaohua Song , Luo Liu , Chunlei Wu , Xiongsheng Sun , Siping Hu
发明人： Xuejun Lao , Runpu Shen , Weidong Ye , Xiaohua Song , Luo Liu , Chunlei Wu , Xiongsheng Sun , Siping Hu
IPC分类号： C07C45/42 , C07C41/30 , C07C43/15
CPC分类号： C07C43/16 , C07C41/30 , C07C45/42 , C07C47/21
摘要： The invention discloses an intermediate 1-methoxyl-2,6,10-trimethyl-1,3,5, 9-undec-tetraene, and a preparation method and uses thereof. In the synthesis method for the current lycopene intermediate 2-pos double bond C-14 aldehyde (2,6,10-trimethyl-2,5,9-undecatriene-1-aldehyde), expensive methyl iodide, polluting dimethyl sulphide and dangerous strong base are needed, so that the method is hardly applied to industrial production. The invention provides a new compound 1-methoxyl-2,6,10-trimethyl-1,3,5,9-undec-tetraene, and pure 2-pos double bond C-14 aldehyde can be prepared by hydrolyzing and refining the compound. The synthetic route is simplified and the great suitability for industrial production is achieved.
摘要翻译：本发明公开了中间体1-甲氧基-2,6,10-三甲基-1,3,5,9-十一四烯及其制备方法和用途。在目前番茄红素中间体2-pos双键C-14醛（2,6,10-三甲基-2,5,9-十一碳三烯-1-醛）的合成方法中，昂贵的甲基碘，污染二甲基硫化物和危险的强需要这种方法，这种方法几乎不适用于工业生产。本发明提供了一种新的化合物1-甲氧基-2,6,10-三甲基-1,3,5,9-十一四烯，纯的2-位双键C-14醛可以通过水解和精制化合物。合成路线简化，实现了工业生产的良好适应性。

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