CAS: 1006376-61-9; Ethyl (1R,2R)-2-(3,4-Difluorophenyl)Cyclopropane-1-Carboxylate

该化合物是一种具有跨形配置和3,4-二氟苯替代成分的手性环丙丙烷衍生物,该化合物因其立体结构,往往能增强生物活动和选择性,对制药和农用化学研究具有重大兴趣;氟丙烯原子的存在提高了代谢稳定性和结合性,使其成为药物发现的宝贵中间体.其高对等美纯度确保了不对称合成的一贯性能.乙基酯组为进一步的功能化提供了多功能性.该产品适合于需要精确立体化学的应用,如研制酶抑制剂或感应感应器.

结构式图片

上下游产品

Ethyl (4R)-4-(3,4-Difluorophenyl)-4-Hydroxybutanoate
乙基4-(3,4-二氟苯基)-4-氧代丁酸酯 Ethyl 4-(3,4-Difluorophenyl)-4-Oxobutyrate 898752-22-2

合成工艺路线路线简述

    1,2-二氟苯置于aluminum (III) Chloride,硼烷四氢呋喃络合物,Sodium T-Butanolate,(S)-2-甲基-Cbs-恶唑硼烷体系中,用 二氯甲烷,甲苯 用作溶剂,化学反应 34.0H,反应生成(1R,2R)-2-(3,4-二氟苯基)环丙烷羧酸乙酯
    参考文献:(1R,2S)-2-(3,4-二氟苯基)环丙胺.d-扁桃 酸盐的制备方法
    标题:(1R,2S)-2-(3,4-二氟苯基)环丙胺.d-扁桃 酸盐的制备方法
    摘要:本发明公开了一种(1R,2S)‑2‑(3,4‑二氟苯基)环丙胺.d‑扁桃酸盐的制备方法,所述方法可以将式ⅴ化合物通过环丙烷化反应得到式ⅳ化合物,经过成酰胺,霍夫曼降解得到式ⅱ化合物,再与d‑扁桃酸成盐得到式ⅰ化合物.所述式ⅴ化合物的制备方法是将结构如式ⅵ所示的化合物通过cbs不对称还原反应得到结构如式ⅴ所示的化合物,所述cbs不对称还原反应的催化剂为结构如式ⅶ所示的化合物,所述cbs不对称还原反应的还原剂选自硼烷‑四氢呋喃或硼烷‑n,N‑二乙基苯胺.

    专利信息


    专利号:EP-2644590-A1
    优先权日:2012-03-30
    标 题:Synthesis of 2-(3,4-difluorophenyl)cyclopropanamine derivatives and salts
    权利人:LEK PHARMACEUTICALS
    摘要:The present invention relates to the field of organic synthesis and describes the synthesis of specific intermediates suitable for the preparation of triazolopyrimidine compounds such as ticagrelor.

    专利号:US-2018148745-A1
    优先权日:2015-05-26
    标题:Hemoprotein catalysts for improved enantioselective enzymatic synthesis of ticagrelor
    发明人:ARNOLD FRANCIS H; RENATA HANS; MCINTOSH JOHN A; LEWIS RUSSELL D; KAN SEK BIK JENNIFER; HERNANDEZ KARI; COELHO PEDRO; ROZZELL DAVID; ZHANG CHEN
    权利人:CALIFORNIA INST OF TECHN; PROVIVI INC
    摘要:The present invention provides methods by which trans-(1R,2S)-2-(3,4-difluorophenyl)-cyclopropylamine and related cyclopropane compounds are prepared using synthetic strategies that include a biocatalytic cyclopropanation step.

    专利号:EP-2628721-A1
    优先权日:2012-02-20
    标题 :Synthesis of 2-(3,4-difluorophenyl)cyclopropanecarboxylic acid

    专利号:WO-2016086015-A1
    优先权日:2014-11-25
    标 题:Myoglobin-based catalysts for carbene transfer reactions
    发明人:FASAN RUDI
    权利人:UNIV ROCHESTER; FASAN RUDI
    摘要:Methods are provided for carrying out carbene transfer transformations such as olefin cyclopropanation reactions, carbene heteroatom-H insertion reactions (heteroatom = N, S, Si), sigmatropic rearrangement reactions, and aldehyde olefination reactions with high efficiency and selectivity by using a novel class of myoglobin-based biocatalysts. These methods are useful for the synthesis of a variety of organic compounds which contain one or more new carbon-carbon or carbon-heteroatom (N, S, or Si) bond. The methods can be applied for conducting these transformations in vitro (i.e., using the biocatalyst in isolated form) and in vivo (i.e., using the biocatalyst in a whole cell system).

    专利号:WO-2016191612-A2
    优先权日:2015-05-26
    标 题 :Hemoprotein catalysts for improved enantioselective enzymatic synthesis of ticagrelor

    专利号:WO-2013124280-A1
    优先权日:2012-02-20
    标 题 :Synthesis of 2-(3,4-difluorophenyl)cyclopropanecarboxylic acid
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    主要参考文献

    参考标题: Myoglobin-Based Catalysts For Carbene Transfer Reactions Catalyseurs à Base De Myoglobine Pour Réactions De Transfert De Carbène
    摘要:Methods Are Provided For Carrying Out Carbene Transfer Transformations Such As Olefin Cyclopropanation Reactions, Carbene Heteroatom-H Insertion Reactions (Heteroatom = N, S, Si), Sigmatropic Rearrangement Reactions, And Aldehyde Olefination Reactions With High Efficiency And Selectivity By Using A Novel Class Of Myoglobin-Based Biocatalysts. These Methods Are Useful For The Synthesis Of A Variety Of Organic Compounds Which Contain One Or More New Carbon-Carbon Or Carbon-Heteroatom (N, S, Or Si) Bond. The Methods Can Be Applied For Conducting These Transformations In Vitro (I.E., Using The Biocatalyst In Isolated Form) And In Vivo (I.E., Using The Biocatalyst In A Whole Cell System).

    合成参考文献


    参考文献:10.1055/s-0036-1590065
    摘要:Asymmetric Cyclopropanation Using Engineered Myoglobin Catalysts. Synfacts. 2017 Feb 15;13(03):0230. doi: 10.1055/s-0036-1590065.
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