Manufacture of isoflavones
    1.
    发明授权
    Manufacture of isoflavones 有权
    异黄酮的制造

    公开(公告)号:US07326797B2

    公开(公告)日:2008-02-05

    申请号:US10521972

    申请日:2003-07-14

    IPC分类号: C07D311/04

    CPC分类号: C07D311/36

    摘要: A process for manufacturing a hydroxylated isoflavone of the formula (I) given in the description comprises re-acting an appropriately substituted 2-hydroxydeoxybenzoin of the formula (II), also given in the description, with a formic acid anhydride of the formula HCOOCOR3, wherein R3 signifies C2-20-alkyl or various other groups as given in the description, in presence of a base or in a solvent which acts as a base, and if necessary promoting the ensuing hydrolysis of the so-produced acylated form of the hydroxylated isoflavone of the formula I by acidification. Of particular interest as products of this process are the 5,7dihydroxyisoflavones, e.g. genistein (5,7,4′-trihydroxyisoflavone). Isoflavones display many useful biochemical effects.

    摘要翻译: 用于制备描述中给出的式(I)的羟基化异黄酮的方法包括将式(II)的适当取代的2-羟基脱氧苯偶姻(也在本说明书中给出)与式HCOOCOR 3的甲酸酐重新作用, 其中R 3表示C 2 2-20 - 烷基或说明书中给出的各种其它基团,在碱的存在下或在作为碱的溶剂中,以及 如果需要,通过酸化促进所产生的酰化形式的式I的羟基化异黄酮的随后的水解。 特别感兴趣的是该方法的产物是5,7-二羟基异黄酮。 染料木素(5,7,4'-三羟基异黄酮)。 异黄酮显示出许多有用的生化作用。

    Cyclic dienol ethers
    3.
    发明授权
    Cyclic dienol ethers 有权
    环状二烯醇醚

    公开(公告)号:US06348606B2

    公开(公告)日:2002-02-19

    申请号:US09764016

    申请日:2001-01-17

    IPC分类号: C07D31708

    摘要: The claimed invention relates to cyclic dienol ethers of formula (III). wherein R3 is hydrogen and R4 is C1-4 alkoxy or R3 and R4 together form an optionally substituted methylenedioxy group —O—C(R5)(R6)—O—, wherein R5 and R6 are each independently hydrogen, C1-4 alkyl or phenyl.

    摘要翻译: 所要求保护的发明涉及式(III)的环状二烯醇醚,其中R3是氢,R4是C1-4烷氧基或R3和R4一起形成任选取代的亚甲二氧基-OC(R 5)(R 6)-O-,其中R 5 和R 6各自独立地为氢,C 1-4烷基或苯基。

    Manufacture of isoflavones
    5.
    发明申请
    Manufacture of isoflavones 有权
    异黄酮的制造

    公开(公告)号:US20050256321A1

    公开(公告)日:2005-11-17

    申请号:US10521972

    申请日:2003-07-14

    CPC分类号: C07D311/36

    摘要: A process for manufacturing a hydroxylated isoflavone of the formula (I) given in the description comprises re-acting an appropriately substituted 2-hydroxydeoxybenzoin of the formula (II), also given in the description, with a formic acid anhydride of the formula HCOOCOR3, wherein R3 signifies C2-20-alkyl or various other groups as given in the description, in presence of a base or in a solvent which acts as a base, and if necessary promoting the ensuing hydrolysis of the so-produced acylated form of the hydroxylated isoflavone of the formula I by acidification. Of particular interest as products of this process are the 5,7dihydroxyisoflavones, e.g. genistein (5,7,4′-trihydroxyisoflavone). Isoflavones display many useful biochemical effects.

    摘要翻译: 用于制备描述中给出的式(I)的羟基化异黄酮的方法包括将式(II)的适当取代的2-羟基脱氧苯偶姻(也在本说明书中给出)与式HCOOCOR 3的甲酸酐重新作用, 其中R 3表示C 2 2-20 - 烷基或说明书中给出的各种其它基团,在碱的存在下或在作为碱的溶剂中,以及 如果需要,通过酸化促进所产生的酰化形式的式I的羟基化异黄酮的随后的水解。 特别感兴趣的是该方法的产物是5,7-二羟基异黄酮。 染料木素(5,7,4'-三羟基异黄酮)。 异黄酮显示出许多有用的生化作用。

    Process for producing 3-hydroxypropionitrile

    公开(公告)号:US06462219B2

    公开(公告)日:2002-10-08

    申请号:US09764549

    申请日:2001-01-17

    IPC分类号: C07C25500

    摘要: A process for the production of 3-hydroxypropionitrile is provided. This process includes (a) reacting acrylonitrile with water at a defined molar ratio in the presence of a weak base under specific temperature and pressure conditions until a conversion in the range of about 40% to about 80% has been achieved; (b) after cooling the mixture obtained in (a), separating off its aqueous phase; (c) distilling off the acrylonitrile from the organic phase remaining after (b); (d) subjecting the mixture obtained in (c) to pyrolysis at specific temperature and pressure conditions in the presence of a basic catalyst to obtain a mixture consisting mainly of 3-hydroxypropionitrile and acrylonitrile; and (e) isolating the desired 3-hydroxypropionitrile by fractional distillation from the mixture obtained in (d). Such a process in which the basic aqueous phase and the acrylonitrile that has been distilled off are recycled represents a preferred embodiment.

    Process for the catalytic dealkoxylation of
1,1,3-trialkoxy-2-methyl-butane
    7.
    发明授权
    Process for the catalytic dealkoxylation of 1,1,3-trialkoxy-2-methyl-butane 失效
    1,1,3-三烷氧基-2-甲基 - 丁烷的催化脱烷基化方法

    公开(公告)号:US5990360A

    公开(公告)日:1999-11-23

    申请号:US76772

    申请日:1998-05-12

    摘要: A novel process for the manufacture of a .gamma.-halotiglic aldehyde HalH.sub.2 C-CH.dbd.C(CH.sub.3)-CHO [I], wherein Hal signifies chlorine or bromine, comprises haloalkoxylating a 1-alkoxy-2-methyl-1,3-butadiene H.sub.2 C.dbd.CH-C (CH.sub.3).dbd.CH-OR.sup.1 [II], wherein R.sup.1 signifies C.sub.1-4 -alkyl, using a particular halogenating agent in a C.sub.1-4 -alkanol (R.sup.2 OH) and hydrolyzing the thus-obtained .gamma.-halotiglic aldehyde dialkyl acetal HalH.sub.2 C-CH.dbd.C(CH.sub.3)-CH (OR.sup.1)(OR.sup.2) [III] to the desired .gamma.-chloro- or .gamma.-bromotiglic aldehyde I. The halogenating agent used in this process is selected from an alkali metal hypochlorite, an alkali metal hypobromite, an alkaline earth metal hypochlorite, an alkaline earth metal hypobromite, tert.butyl hypochlorite, N-bromoacetamide, 1.3-dichloro-5,5-dimethylhydantoin and 1,3-dibromo-5,5-dimethylhydantoin. Further aspects of the present invention are the use of the thus manufactured .gamma.-halotiglic aldehyde for the production of .gamma.-acetoxy-tiglic aldehyde or of a Wittig aldehyde halide Hal-Ph.sub.3 P.sup.+ CH.sub.2 -CH.dbd.C(CH.sub.3)-CHO [VII], wherein Hal signifies chlorine or bromine and Ph a process for the catalytic dealkoxylation of the 1,1,3-trialkoxy-2-methyl-butane CH.sub.3 -CH(ORl)-CH(CH.sub.3)-CH(OR.sup.1).sub.2 [VI] to the corresponding 1-alkoxy-2-methyl-1,3-butadiene II in the gas phase using an aluminium silicate of medium specific surface as the catalyst. The products I, .gamma.-acetoxy-tiglic aldehyde and VII are known, important intermediates for the production of various apocarotenoids and diapocarotenoids as well as of Vitamin A.

    摘要翻译: 用于制备γ-卤代醛HalH2C-CH = C(CH3)-CHO [I]的新方法,其中Hal表示氯或溴,包括1-烷氧基-2-甲基-1,3-丁二烯H 2 C的卤代烷氧基化 = CH-C(CH 3)= CH-OR 1 [II],其中R 1表示C 1-4 - 烷基,使用特定的卤化剂在C 1-4链烷醇(R 2 OH)中并水解由此得到的γ-卤代二烷基 缩醛HalH2C-CH = C(CH3)-CH(OR1)(OR2)[III]到所需的γ-氯 - 或γ-溴代醛I.本方法中使用的卤化剂选自碱金属次氯酸盐, 碱金属次溴酸盐,碱土金属次氯酸盐,碱土金属次溴酸盐,叔丁基次氯酸盐,N-溴乙酰胺,1,3-二氯-5,5-二甲基乙内酰脲和1,3-二溴-5,5-二甲基乙内酰脲。 本发明的其它方面是使用如此制备的γ-卤代醛用于制备γ-乙酰氧基 - 四氢呋喃或维蒂希醛卤化物Hal-Ph 3 P + CH 2 -CH = C(CH 3)-CHO [VII] 其中Hal表示氯或溴,Ph表示1,1,3-三烷氧基-2-甲基 - 丁烷CH 3 -CH(OR 1)-CH(CH 3)-CH(OR 1)2 [VI]的催化脱烷基化方法, 使用中等比表面积的硅酸铝作为催化剂,在气相中与相应的1-烷氧基-2-甲基-1,3-丁二烯II反应。 产物I,γ-乙酰氧基 - lic醛和Ⅶ是已知的,用于生产各种类胡萝卜素和二糖皮质素以及维生素A的重要中间体。

    Process for making 4,4′-diketo-carotenoids
    9.
    发明授权
    Process for making 4,4′-diketo-carotenoids 有权
    制备4,4'-二酮类胡萝卜素的方法

    公开(公告)号:US06201155B1

    公开(公告)日:2001-03-13

    申请号:US09368046

    申请日:1999-08-03

    IPC分类号: C07C4561

    摘要: A process for the manufacture of a symmetrical, terminally ring-substituted polyenes by reacting a polyene di(O,O-dialkyl acetal) with a cyclic dienol ether in the presence of a Lewis or Brönsted acid, hydrolyzing the condensation product resulting therefrom and cleaving off alcohol under basic or acidic conditions from the polyene derivative produced at this stage. The novel cyclic dienol ethers, as well as, novel intermediates resulting from the condensation and additional intermediates in this process form further aspects of the invention. The final products are primarily carotenoids, which find corresponding use, e.g., as colorings and pigments for foodstuffs, animal products, etc.

    摘要翻译: 通过在路易斯或布朗斯台德酸存在下使多烯二(O,O-二烷基缩醛)与环状二烯醇醚反应来制造对称的末端环取代的多烯的方法,水解由此产生的缩合产物和裂解 在碱性或酸性条件下从在此阶段产生的多烯衍生物脱除醇。 该新型环状二烯醇醚以及由该缩合产生的新型中间体以及该方法中的其它中间体形成本发明的其它方面。 最终产品主要是类胡萝卜素,其可以用于食品,动物产品等的相关用途,例如着色剂和颜料。

    Process for the manufacture of a gamma-halotiglic aldehyde
    10.
    发明授权
    Process for the manufacture of a gamma-halotiglic aldehyde 失效
    制备γ-卤代醛的方法

    公开(公告)号:US5786518A

    公开(公告)日:1998-07-28

    申请号:US904523

    申请日:1997-08-01

    摘要: A novel process for the manufacture of a .gamma.-halotiglic aldehyde HalH.sub.2 C--CH.dbd.C(CH.sub.3)--CHO �I!, wherein Hal signifies chlorine or bromine, comprises haloalkoxylating a 1-alkoxy-2-methyl-1,3-butadiene H.sub.2 C.dbd.CH--C(CH.sub.3).dbd.CH--OR.sup.1 �II!, wherein R.sup.1 signifies C.sub.1-4 -alkyl, using a particular halogenating agent in a C.sub.1-4 -alkanol (R.sup.2 OH) and hydrolyzing the thus-obtained .gamma.-halotiglic aldehyde dialkyl acetal HalH.sub.2 C--CH.dbd.C(CH.sub.3)--CH(OR.sup.1)(OR.sup.2) �III! to the desired .gamma.-chloro- or .gamma.-bromotiglic aldehyde I. The halogenating agent used in this process is selected from an alkali metal hypochlorite, an alkali metal hypobromite, an alkaline earth metal hypochlorite, an alkaline earth metal hypobromite, tert.butyl hypochlorite, N-bromoacetamide, 1.3-dichloro-5,5-dimethylhydantoin and 1,3-dibromo-5,5-dimethylhydantoin. Further aspects of the present invention are the use of the thus-manufactured .gamma.-halotiglic aldehyde for the production of .gamma.-acetoxy-tiglic aldehyde or of a Wittig aldehyde halide Hal-Ph.sub.3 P.sup.+ CH.sub.2 --CH.dbd.C(CH.sub.3)--CHO �VII!, wherein Hal signifies chlorine or bromine and Ph signifies phenyl, as well as a process for the catalytic dealkoxylation of the 1,1,3-trialkoxy-2-methyl-butane CH.sub.3 --CH(OR.sup.1)--CH(CH.sub.3)--CH(OR.sup.1).sub.2 �VI! to the corresponding 1-alkoxy-2-methyl-1,3-butadiene II in the gas phase using an aluminium silicate of medium specific surface as the catalyst. The products I, .gamma.-acetoxy-tiglic aldehyde and VII are known, important intermediates for the production of various apocarotenoids and diapocarotenoids as well as of Vitamin A.

    摘要翻译: 用于制备γ-卤代醛HalH2C-CH = C(CH3)-CHO [I]的新方法,其中Hal表示氯或溴,包括1-烷氧基-2-甲基-1,3-丁二烯H 2 C的卤代烷氧基化 = CH-C(CH 3)= CH-OR 1 [II],其中R 1表示C 1-4 - 烷基,使用特定的卤化剂在C 1-4链烷醇(R 2 OH)中并水解由此得到的γ-卤代二烷基 缩醛HalH2C-CH = C(CH3)-CH(OR1)(OR2)[III]到所需的γ-氯 - 或γ-溴代醛I.本方法中使用的卤化剂选自碱金属次氯酸盐, 碱金属次溴酸盐,碱土金属次氯酸盐,碱土金属次溴酸盐,叔丁基次氯酸盐,N-溴乙酰胺,1,3-二氯-5,5-二甲基乙内酰脲和1,3-二溴-5,5-二甲基乙内酰脲。 本发明的其它方面是使用如此制备的γ-卤代醛用于制备γ-乙酰氧基 - 四氢呋喃或维蒂希醛卤化物Hal-Ph 3 P + CH 2 -CH = C(CH 3)-CHO [VII ],其中Hal表示氯或溴,Ph表示苯基,以及1,1,3-三烷氧基-2-甲基 - 丁烷CH3-CH(OR1)-CH(CH3)-CH(CH)的催化脱烷基化方法 (OR1)2 [VI]与相应的1-烷氧基-2-甲基-1,3-丁二烯II在气相中使用中等比表面积的硅酸铝作为催化剂。 产物I,γ-乙酰氧基 - lic醛和Ⅶ是已知的,用于生产各种类胡萝卜素和二糖皮质素以及维生素A的重要中间体。