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    • 1. 发明授权
    • Process for preparing heterocyclic (R)- and (S)-cyanohydrins
    • 制备杂环(R) - 和(S) - 氰基醇的方法
    • US07052885B2
    • 2006-05-30
    • US10325922
    • 2002-12-23
    • Peter PoechlauerWolfgang SkrancHerbert MayrhoferIrma WirthRudolf NeuhoferHerfried GrienglMartin Fechter
    • Peter PoechlauerWolfgang SkrancHerbert MayrhoferIrma WirthRudolf NeuhoferHerfried GrienglMartin Fechter
    • C12P17/00C12P17/02C12P17/04C12P17/06C12P17/18
    • C12P13/004C12P17/00C12P17/04
    • A process for preparing enantiomer-enriched heterocyclic (R)- and (S)-cyanohydrins of the formula (I), where R1, R2, R3, R4 independently of one another are H, an unsubstituted or substituted C1–C24-alkyl, alkenyl or alkynyl radical, where one or more carbon atoms in the chain can be replaced by an oxygen atom, a nitrogen atom, a sulfur atom, an SO or an SO2 group, an unsubstituted or substituted aryl or heteroaryl radical or heterocyclic radical or halogen, hydroxyl, NR5R6, acetyl, oxo, C1–C6-carbalkoxy, C1–C6-carbalkoxyamino, COOR7, cyano, amide, benzoylamino or NO2,R5 and R6 are H, C1–C6-alkyl radical, phenyl radical, benzyl radical or COOR7, or together form a C2–C8-alkylene or heteroalkylene radical,R7 is H or C1–C6-alkyl,n is 0, 1, 2 or 3,X, Y and Z can be an unsubstituted or substituted carbon atom or a radical selected from the group consisting of N, O, S or NR5R6, where R5 and R6 are as defined above, SO or SO2, and at least one of the radicals X, Y and Z is not a carbon atom, where the compounds of the formula (I) can have one or more double bonds in the ring, with the proviso that in a 5-membered ring the double bond is not conjugated with the —C(OH)CN-group, and/or can be anellated and/or bridged,by reacting a ketone of the formula (II), where R1, R2, R3, R4, X, Y, Z and n have the meanings above, with an (R)- or (S)-hydroxynitrile lyase in an organic, aqueous or two-phase system, or in emulsion, in the presence of a cyanide group donor.
    • 制备式(I)的对映异构体富集的杂环(R) - 和(S) - 氰基醇的方法,其中R 1,R 2,R 3,R 4彼此独立地是H,未取代或取代的C 1 - 链烯基或炔基,其中链中的一个或多个碳原子可以被氧原子,氮原子,硫原子,SO或 SO 2 2基团,未取代或取代的芳基或杂芳基或杂环基或卤素,羟基,NR 5 R 6,乙酰基,氧代C 1 -C 6 - 亚烷基氧基,C 1 -C 6 - 烷氧基氨基,COOR 7,氰基,酰胺,苯甲酰氨基或NO 2,R 5和R 6是H C 1 -C 6 - 烷基,苯基,苄基或COOR 7,或一起形成C 1 -C 6 - 8亚烷基或杂亚烷基,R 7是H或C 1 -C 6 - 烷基,n是0,1,2或3,X,Y 并且Z可以是未取代或取代的碳原子或选自它的基团 由N,O,S或NR5R6组成的基团,其中R 5和R 6如上定义,SO或SO 2,并且基团X,Y和Z中的至少一个不是碳 原子,其中式(I)的化合物可以在环中具有一个或多个双键,条件是在5元环中双键不与-C(OH)CN-基团共轭,并且 /或可以通过使式(II)的酮(其中R 1,R 2,R 3,R 4,X,Y,Z和n具有上述含义)与(R) - 或( S) - 羟基腈裂解酶在有机,水相或两相体系中,或在乳液中,在氰化物基团给体存在下。
    • 2. 发明授权
    • Process for preparing protected, enantiomer-enriched cyanohydrins by in-situ derivatization
    • 通过原位衍生制备保护的富含对映异构体的氰醇的方法
    • US06909011B2
    • 2005-06-21
    • US10325923
    • 2002-12-23
    • Wolfgang SkrancPeter PoechlauerIrma WirthRudolf NeuhoferHerbert Mayrhofer
    • Wolfgang SkrancPeter PoechlauerIrma WirthRudolf NeuhoferHerbert Mayrhofer
    • C12P13/00C12R1/91C07C253/16C12P13/16
    • C12P13/004
    • A process for preparing protected, enantiomer-enriched cyanohydrins of the formula where R1 and R2 independently of one another can be an unsubstituted, monosubstituted or polysubstituted C1-C20-alkyl, C5-C20-aryl, C5-C20-heteroaryl, C5-C20-alkaryl, C5-C20-alkylheteroaryl or C5-C20-aralkyl radical or an unsubstituted, monosubstituted or polysubstituted C5-C20-heterocycle, or C5-C20-alkylheterocycle or together can be an unsubstituted or substituted C4-C20-alkylene radical, which can contain one or more heteroatoms in the chain, or one of the radicals is hydrogen, and R3 can be an unsubstituted or substituted C1-C20-alkyl, C5-C20-aryl or C5-C20-heteroaryl radical, by reacting an aldehyde or ketone of the formula where R1 and R2 are defined as above, in the presence of an (R)- or (S)-hydroxynitrile lyase in an organic, aqueous or 2-phase system or in emulsion at a temperature of −5 to +40° C. with a carbonic ester nitrile of the formula where R3 is defined as above.
    • 制备具有下式的受保护的对映异构体富含氰醇的方法其中R 1和R 2彼此独立地可以是未取代的,单取代的或多取代的C 1 -C 20 - 烷基 C 5 -C 20 - 芳基,C 5 -C 20 - 杂芳基,C 5 - C 20 -C 20 - 烷芳基,C 5 -C 20 - 烷基杂芳基或C 5 -C 或是未取代的单取代或多取代的C 5 -C 20 - 杂环或C 5 - -C 20 - 烷基杂环或一起可以是未取代或取代的C 4 -C 20 - 亚烷基,其可以含有一个或多个杂原子 在链中,或者一个基团是氢,并且R 3可以是未取代或取代的C 1 -C 20 - 烷基,C 5 C 20 -C 20 - 芳基或C 5 -C 20 - 杂芳基,通过使下式的醛或酮反应其中R1和R2 在有机,水相或两相体系中的(R) - 或(S) - 羟基腈裂解酶存在下,或在-5至+ 40℃的温度下与碳酸酯 腈,其中R3如上定义。
    • 6. 发明授权
    • Process for the production of cyclopropane derivatives
    • 制备环丙烷衍生物的方法
    • US08497384B2
    • 2013-07-30
    • US13129213
    • 2009-11-12
    • Mehul ThathagarPeter PoechlauerSascha Braune
    • Mehul ThathagarPeter PoechlauerSascha Braune
    • C07D333/78
    • C07B37/10C07D333/78Y02P20/582
    • A process for the preparation of a cyclopropane derivative of Formula (I), by reacting an olefin of Formula (II), with a carbene of the formula:CR1R2, in a reaction vessel, optionally in the presence of a solvent, wherein, R1 and R2 are each independently hydrogen, C1-C6 alkyl, C2-C6 alkenyl, aryl, heteroaryl, heterocyclyl, carbocyclyl, heterocyclyl, —C(O)R7 or —NR82; R3, R4, R5 and R6 are each independently hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, aryl, aryloxy, heteroaryl, heterocyclyl, carbocyclyl, heterocyclyl, —C(O)R9, —NR102, —SR11, —S(O)R11, or —SO2R11, or R3 and R6 are as defined above and R4 and R5 together form a ring, which ring is carbocyclyl, heterocyclyl, aromatic or heteroaromatic; R7 is hydrogen, hydroxy, C1-C6 alkyl, C1-C6 alkoxy, aryl, aryloxy, heteroaryl or —NR102; R8 is hydrogen, C1-C6 alkyl, C1-C6 alkenyl, aryl, heteroaryl, carbocyclyl or heterocyclyl; R9 is hydrogen, hydroxy, C1-C6 alkyl, C1-C6 alkoxy, aryl, aryloxy or heteroaryl; R10 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, aryl, heteroaryl, carbocyclyl, heterocyclyl or C(O)R12; R11 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, aryl, heteroaryl, carbocyclyl or heterocyclyl; and R12 is hydrogen, hydroxy, C1-C6 alkyl, C1-C6 alkoxy, aryl, or aryloxy, in the presence of copper metal or copper oxide, wherein the process is a continuous process.
    • 一种制备式(I)的环丙烷衍生物的方法,通过使式(II)的烯烃与式CR1R2的卡宾反应在反应容器中,任选地在溶剂存在下,其中R 1 C 1 -C 6烷基,C 2 -C 6烯基,芳基,杂芳基,杂环基,碳环基,杂环基,-C(O)R 7或-NR 82; R3,R4,R5和R6各自独立地为氢,C1-C6烷基,C1-C6烷氧基,C2-C6烯基,芳基,芳氧基,杂芳基,杂环基,碳环基,杂环基,-C(O)R9,-NR102, SR11,-S(O)R11或-SO2R11,或R3和R6如上定义,R4和R5一起形成环,该环是碳环基,杂环基,芳族或杂芳族; R 7是氢,羟基,C 1 -C 6烷基,C 1 -C 6烷氧基,芳基,芳氧基,杂芳基或-NR 102; R 8是氢,C 1 -C 6烷基,C 1 -C 6烯基,芳基,杂芳基,碳环基或杂环基; R9是氢,羟基,C1-C6烷基,C1-C6烷氧基,芳基,芳氧基或杂芳基; R 10是氢,C 1 -C 6烷基,C 2 -C 6烯基,芳基,杂芳基,碳环基,杂环基或C(O)R 12; R11是氢,C1-C6烷基,C2-C6烯基,芳基,杂芳基,碳环基或杂环基; 并且在铜金属或氧化铜的存在下,R 12是氢,羟基,C 1 -C 6烷基,C 1 -C 6烷氧基,芳基或芳氧基,其中该方法是连续方法。
    • 10. 发明申请
    • PROCESS FOR THE PRODUCTION OF CYCLOPROPANE DERIVATIVES
    • 生产环丙基衍生物的方法
    • US20110301359A1
    • 2011-12-08
    • US13129213
    • 2009-11-12
    • Mehul ThathagarPeter PoechlauerSascha Braune
    • Mehul ThathagarPeter PoechlauerSascha Braune
    • C07D333/78
    • C07B37/10C07D333/78Y02P20/582
    • A process for the preparation of a cyclopropane derivative of Formula (I), by reacting an olefin of Formula (II), with a carbene of the formula: CR1R2, in a reaction vessel, optionally in the presence of a solvent, wherein, R1 and R2 are each independently hydrogen, C1-C6 alkyl, C2-C6 alkenyl, aryl, heteroaryl, heterocyclyl, carbocyclyl, heterocyclyl, —C(O)R7 or —NR82; R3, R4, R5 and R6 are each independently hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, aryl, aryloxy, heteroaryl, heterocyclyl, carbocyclyl, heterocyclyl, —C(O)R9, —NR102, —SR11, —S(O)R11, or —SO2R11, or R3 and R6 are as defined above and R4 and R5 together form a ring, which ring is carbocyclyl, heterocyclyl, aromatic or heteroaromatic; R7 is hydrogen, hydroxy, C1-C6 alkyl, C1-C6 alkoxy, aryl, aryloxy, heteroaryl or —NR102; R8 is hydrogen, C1-C6 alkyl, C1-C6 alkenyl, aryl, heteroaryl, carbocyclyl or heterocyclyl; R9 is hydrogen, hydroxy, C1-C6 alkyl, C1-C6 alkoxy, aryl, aryloxy or heteroaryl; R10 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, aryl, heteroaryl, carbocyclyl, heterocyclyl or C(O)R12; R11 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, aryl, heteroaryl, carbocyclyl or heterocyclyl; and R12 is hydrogen, hydroxy, C1-C6 alkyl, C1-C6 alkoxy, aryl, or aryloxy, in the presence of copper metal or copper oxide, wherein the process is a continuous process.
    • 一种制备式(I)的环丙烷衍生物的方法,通过使式(II)的烯烃与式CR1R2的卡宾反应在反应容器中,任选地在溶剂存在下,其中R 1 C 1 -C 6烷基,C 2 -C 6烯基,芳基,杂芳基,杂环基,碳环基,杂环基,-C(O)R 7或-NR 82; R3,R4,R5和R6各自独立地为氢,C1-C6烷基,C1-C6烷氧基,C2-C6烯基,芳基,芳氧基,杂芳基,杂环基,碳环基,杂环基,-C(O)R9,-NR102, SR11,-S(O)R11或-SO2R11,或R3和R6如上定义,R4和R5一起形成环,该环是碳环基,杂环基,芳族或杂芳族; R 7是氢,羟基,C 1 -C 6烷基,C 1 -C 6烷氧基,芳基,芳氧基,杂芳基或-NR 102; R 8是氢,C 1 -C 6烷基,C 1 -C 6烯基,芳基,杂芳基,碳环基或杂环基; R9是氢,羟基,C1-C6烷基,C1-C6烷氧基,芳基,芳氧基或杂芳基; R 10是氢,C 1 -C 6烷基,C 2 -C 6烯基,芳基,杂芳基,碳环基,杂环基或C(O)R 12; R11是氢,C1-C6烷基,C2-C6烯基,芳基,杂芳基,碳环基或杂环基; 并且在铜金属或氧化铜的存在下,R 12是氢,羟基,C 1 -C 6烷基,C 1 -C 6烷氧基,芳基或芳氧基,其中该方法是连续方法。