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    • 44. 发明申请
    • MONOETHERIFIED DIOLS OF DIAMONDOIDS
    • 单一的DIAMONDOID DIOLS
    • US20110124912A1
    • 2011-05-26
    • US12996399
    • 2009-06-02
    • Peter R. SchreinerHartmut Schwertfeger
    • Peter R. SchreinerHartmut Schwertfeger
    • C07C227/02C07C43/196C07C41/09C07C231/06C07C213/02
    • C07C41/09C07C43/196C07C215/44C07C217/52C07C229/50C07C233/23C07C2603/90Y02P20/55
    • The invention at hand describes functionalized diols of diamondoids, in which one of the two hydroxy groups is masked by a protective group, as well as methods for producing these functionalized diols. The protective group is a group —CHR1R2, wherein R1 and R2 stand for alkyl groups and the protective group comprises at least one halogen atom. The monoethers of the diamondoid diols according to the present invention are produced by reacting the diamondoid diol with a halogenated alcohol CHOHR1R2 in the presence of a catalyst acid.The monoetherified diols allow for the targeted production of derivatives of diamondoids, for example, of the corresponding aminoalcohols and aminocarboxylic acids. For that purpose, the diamondoid monoether is reacted in a first step with a halogen nitrile in a Ritter reaction to the corresponding monoether amide. From this monoether amide, the corresponding aminoalcohol can be produced by reacting the protective group —CHR1R2 first with trifluoroacetic acid to the alkanoyloxy group and by subsequently obtaining the aminoalcohol by reaction with thiourea, ethanol and glacial acetic acid.The aminoalcohol can be reacted with a sulfuric acid/formic acid or oleum/formic acid to the corresponding aminocarboxylic acid.The amino, hydroxy and carboxylic groups of the diamondoids can be converted into many other functional groups.
    • 本发明描述了金刚石的官能化二醇,其中两个羟基中的一个被保护基掩蔽,以及制备这些官能化二醇的方法。 保护基是基团-CHR1R2,其中R1和R2代表烷基,保护基包括至少一个卤素原子。 根据本发明的金刚石二醇的单醚通过在催化剂酸的存在下使类金刚石二醇与卤代醇CHOHR1R2反应来制备。 单醚化的二醇允许目标生成类金刚石衍生物,例如相应的氨基醇和氨基羧酸。 为此,金刚石单醚在第一步中与Ritter反应中的卤素腈与相应的单醚酰胺反应。 从该单醚酰胺可以通过使保护基-CHR1R2与三氟乙酸首先与烷酰氧基反应,随后通过与硫脲,乙醇和冰醋酸反应得到氨基醇来制备相应的氨基醇。 氨基醇可以与硫酸/甲酸或发烟硫酸/甲酸反应至相应的氨基羧酸。 金刚石的氨基,羟基和羧基可以转化为许多其他官能团。