利索-全球专利检索

  1. 登录
  2. 注册

搜索结果

3 条记录 (耗时 0.009 秒)

    Method for preparing optically active 5-methyl-2-(1-methyl-butyl)-5-propyl-1,3-dioxan
    1.
    发明授权
    Method for preparing optically active 5-methyl-2-(1-methyl-butyl)-5-propyl-1,3-dioxan 有权
    光学活性5-甲基-2-（1-甲基 - 丁基）-5-丙基-1,3-二恶烷的制备方法

    公开(公告)号：US06297390B1

    公开(公告)日：2001-10-02

    申请号：US09462706

    申请日：2000-04-03

    申请人： Thomas Markert ,  Dirk Merkel ,  Hans-Josef Altenbach

    发明人： Thomas Markert ,  Dirk Merkel ,  Hans-Josef Altenbach

    IPC分类号： C07D31906

    CPC分类号： C11B9/008 ,  C07D319/06

    摘要： The present invention relates to a method for preparing optically active 5-methtyl-2-(1-methtyl-butyl)-5-propyl-1,3-dioxan, wherein said method comprises the following steps: converting lactic acid methylic ester into the corresponding N,N-disubstituted amid (aminolysis with piperidine and/or pyrrolidine); protecting its free OH function by a reaction with ethylvinylether in the presence of p-pyridiniumtosylate as a catalyst; submitting the N-pentamethylen- or N-tetramethylenlactamide thus obtained to a Grignard reaction in a conventional way so as to produce the corresponding &agr;, &bgr;-unsaturated ketone; further separating in a conventional way (e.g. agitation with acetic acid) the protection group introduced during the second step; acetalating in a conventional way the ketone function (e.g. by reaction with 2-methyl-2-propyl-1,3-propanediol); mesylating the free OH function by reaction with methansulfonic acid chloride in pyridine; submitting the intermediate thus obtained to a reducing 1,2-transposition in the presence of trimethylammonium and diisobutylaluminum hydride while maintaining the sterochemistry; and converting by catalytic hydrogenation the dehydro compound thus abtained into optically active 5-methyl-2-(1-methyl-butyl)-5-propyl-1,3-dioxan. The optically active 5-methyl-2-(1-methyl-butyl)-5-propyl-1,3-dioxan of the present invention exhibits a remarkable scent profile as well as a high scent intensity and may be used as perfume.

    摘要翻译： 本发明涉及一种制备光学活性的5-甲基-2-（1-甲基 - 丁基）-5-丙基-1,3-二恶烷的方法，其中所述方法包括以下步骤：将乳酸甲酯转化为 相应的N，N-二取代的酰胺（用哌啶和/或吡咯烷进行氨解）; 在对 - 吡啶鎓甲苯磺酸盐作催化剂存在下，与乙基乙烯基醚反应保护其游离OH官能团; 将这样得到的N-五亚甲基或N-四亚甲基乳酰胺以常规方式进行格氏反应，以制备相应的α，β-不饱和酮; 以常规方式（例如用乙酸搅拌）进一步分离在第二步骤期间引入的保护基团; 以常规方式缩醛化酮功能（例如通过与2-甲基-2-丙基-1,3-丙二醇反应）; 通过与吡啶中的甲磺酸氯化物反应来甲酰化游离OH官能团; 将由此获得的中间体在三甲基铵和二异丁基氢化铝存在下进行还原的1,2-位置转化，同时保持该化学结构; 并通过催化氢化转化得到的脱氢化合物得到光学活性的5-甲基-2-（1-甲基 - 丁基）-5-丙基-1,3-二恶烷。 本发明的光学活性的5-甲基-2-（1-甲基 - 丁基）-5-丙基-1,3-二恶烷显示出显着的香味和强烈的香味，可用作香料。