Cyclic ketones, their preparation and their use in the synthesis of amino acids
    92.
    发明授权
    Cyclic ketones, their preparation and their use in the synthesis of amino acids 失效
    循环酮,其制备及其在氨基酸合成中的应用

    公开(公告)号:US06872856B2

    公开(公告)日:2005-03-29

    申请号:US10312065

    申请日:2001-06-28

    摘要: A method is provided for making an enantiomerically pure compound of the formula: in which R and R′ represent C1?C10 alkyl, C2?C10 alkenyl or C3?C10 cycloalkyl and the wedges signify (S)- or (R)-stereochemistry, the substituents in compound (II) being trans. Conjugate addition is carried out between an organometallic nucleophile that provides a group R as defined above and (R)-4-acetoxycyclopent-2-en-1-one, (S)-4-acetoxycyclopent-2-en-1-one or a similar compound in which acetoxy is replaced by another leaving group to give, e.g. in the case of the acetoxy compound, a trans 3,4-disubstituted addition product of formula III or IV; The acetyl group is eliminated from the addition product to give an (R)- or (S)-4-alkyl or 4-alkenyl cyclopent-2-en-1-one the compound of formula is then to be hydrogenated to give a cyclopentanone of formula (I) or conjugate addition of a second organometallic nucleophile that provides a group R′ as defined above to the compound of the above formula may be carried out to give a trans 3,4-disubstituted addition product of formula (II). One of the above compounds may be converted e.g. via an intermediate (XV)-(XVIII) (in which the substituents R and R′ and the wedges have the meanings indicated above) to a gabapentin analogue of one of the formulae shown below: in which the substituents R and R′ and the wedges also have the meanings indicated above.

    摘要翻译: 提供了一种制备具有下式的对映异构体纯的化合物的方法:其中R和R'代表C 1 -C 10烷基,C 2 -C 10烯基或C 3 -C 10环烷基,楔形表示(S) - 或(R) - 立体化学, 化合物(II)中的取代基是反式的。 在提供如上所定义的基团R的有机金属亲核试剂和(R)-4-乙酰氧基环戊-2-烯-1-酮,(S)-4-乙酰氧基环戊-2-烯-1-酮或(S)-4-乙酰氧基环戊-2-烯-1-酮之间进行共轭加成 类似的化合物,其中乙酰氧基被另一个离去基团取代,例如 在乙酰氧基化合物的情况下,式III或IV的反式3,4-二取代的加成产物; 从加成产物中除去乙酰基,得到(R) - 或(S)-4-烷基或4-烯基环戊-2-烯-1-酮,然后氢化得到环戊酮 可以进行式(I)化合物的共轭加成或向上述化合物提供如上定义的基团R'的第二有机金属亲核试剂的共轭加成,得到式(II)的反式3,4-二取代的加成产物。 上述化合物之一可以被转化为例如。 (XV) - (XVIII)(其中取代基R和R'和楔子具有上述含义)与下列通式所示的加巴喷丁类似物反应:其中取代基R和R'和 楔子也具有上述含义。

    Process for the preparation of organic compounds with manganese cataylsts or the like
    95.
    发明申请
    Process for the preparation of organic compounds with manganese cataylsts or the like 失效
    用锰催化剂等制备有机化合物的方法

    公开(公告)号:US20020165416A1

    公开(公告)日:2002-11-07

    申请号:US09959843

    申请日:2001-11-09

    摘要: A process of the present invention produces an organic compound by allowing a compound containing an electron attractive group of following Formula (1): 1 wherein Y is an electron attractive group; and Rb and Rc are each a hydrogen atom or an organic group, where Y, Rb and Rc may respectively be combined with each other to form a ring with an adjacent carbon atom, to react with a compound containing an unsaturated carbon-carbon bond of following Formula (2) or 2 wherein Rd, Re, Rf, Rg, Ri and Rj are each a hydrogen atom or an organic group, where Rd, Re, Rf and Rg may respectively be combined to form a ring with one or two adjacent carbon atoms, and Ri and Rj may be combined to form a ring with adjacent two carbon atoms, in the presence of oxygen and a catalytic compound of a Group 5, 6, 7, 8 or 9 element of the Periodic Table of Elements to yield a compound of following Formula (3) or (8): 3 wherein Z is a hydrogen atom or a hydroxyl group; and Y, Rb, Rc, Rd, Re, Rf, Rg, Ri and Rj have the same meanings as defined above. This process can efficiently produce a compound having an alkyl group or alkenyl group bonded at the alpha position of an electron attractive group, or a derivative thereof, by catalytic radical addition reaction.

    摘要翻译: 本发明的方法通过使含有下式(1)的吸电子基团的化合物,其中Y为吸电子基团,生成有机化合物; R b和R c各自为氢原子或有机基团,其中Y,Rb和Rc可以分别彼此结合形成具有相邻碳原子的环,与含有不饱和碳 - 碳键的化合物反应 下式(2)或其中R d,R e,R f,R g,R i和R j各自为氢原子或有机基团,其中R d,R e,R f和R g可以分别结合形成具有一个或两个相邻碳原子的环 原子,并且R 1和R 1可以在氧的存在下和元素周期表第5,6,7,8或9族元素的催化化合物的存在下结合形成具有相邻的两个碳原子的环,得到 下式(3)或(8)的化合物:其中Z是氢原子或羟基; Y,Rb,Rc,Rd,Re,Rf,Rg,R 1和R j具有与上述相同的含义。 该方法可以通过催化自由基加成反应有效地制备具有在吸电子基团的α位上键合的烷基或烯基的化合物或其衍生物。

    Method for producing cyclopentanone and cyclopentene-1-carboxylic acid and their esters
    96.
    发明授权
    Method for producing cyclopentanone and cyclopentene-1-carboxylic acid and their esters 失效
    环戊酮和环戊烯-1-羧酸及其酯的制备方法

    公开(公告)号:US06316659B1

    公开(公告)日:2001-11-13

    申请号:US09508008

    申请日:2000-03-07

    IPC分类号: C07C6974

    摘要: A process for preparing cyclopentanone and cyclopentene-1-carboxylic acid or an ester thereof of the formula I where R is hydrogen or an aliphatic radical having 1-6 carbon atoms or a cycloaliphatic, araliphatic or aromatic radical having 6-12 carbon atoms comprises heating a compound of the formula II X—(CH2)4—COOR  II where X is formyl or hydroxymethyl and R is defined as above, and/or a compound which is converted into a compound of the formula II by reaction with water or alcohols ROH under the reaction conditions to from 200 to 450° C. in the gas or liquid phase in the presence of a heterogeneous oxidic catalyst.

    摘要翻译: 制备式I的环戊酮和环戊烯-1-羧酸或其酯的方法,其中R是氢或具有1-6个碳原子的脂族基团或具有6-12个碳原子的脂环族,芳脂族或芳族基团包括加热 式II的化合物,其中X是甲酰基或羟甲基,R如上定义,和/或在反应条件下与水或醇ROH反应转化为式II化合物的化合物为200-450℃ 在气相或液相中存在非均相氧化催化剂。