CAS: 734-32-7; Norandrostenedione

该化合物是一种自然产生的类固醇激素,是硝化酮的前体,一种强效代谢剂,在睾酮和雌激素的生物合成中发挥着关键作用,使其在代谢和内分泌研究中占有重要地位;该化合物的特点是其19个北结构,它与和腐蚀物相比,加强了其代谢和诱导比率;这种特性使得其在肌肉生长,骨密度和激素调控方面的研究有用;其稳定性和生物利用率也有助于其在药物和生物化学研究中的适用性;适当处理和遵守管制准则至关重要,因为它在体育中可能被滥用.

结构式图片

欧盟法规

REACH注册ECHA物质C&L通报REACH预注册

上下游产品

pyridine 4β-bromo-5β-estrane-3,17-dione 19-nortestosterone (10)-diene17,17-ethanediyldioxy-3-methoxy-estra-2,5(10)-diene19-nor-5β-androstane-3,17-dione norethandrolone norethisterone 19-nortestosterone

合成工艺路线路线简述

    诺龙置于氧气,Sodium Acetate体系中,用 水,碳酸二乙酯 作为反应溶剂,100.0 °C,5.0 Mpa 条件下,反应 4.0H,反应生成 19-去甲-4-雄烯二酮
    参考文献:钯纳米粒子在水性介质中作为绿色和可持续氧化功能化醇的催化剂
    标题:钯纳米粒子在水性介质中作为绿色和可持续氧化功能化醇的催化剂
    摘要:先前描述的用于酒精的好氧氧化的催化剂体系包括乙酸钯(II)与新环丙氨酸在水和与水混溶的助溶剂(如碳酸亚乙酯或二甲基亚砜)1:1混合物中的组合,其中涉及到钯纳米颗粒活性催化剂.后者是在原位形成的,或者可以通过用氢气还原钯-新古铜络合物来制备,并且它们都可以被新铜环素配体和助溶剂稳定.该催化剂体系已成功用于甾族仲醇,Nandrolone和5α-Pregnan-3α-Ol-20-One的有氧选择性氧化为相应的酮.
    DOI:10.1016/j.Tet.2009.11.007

    海关参考信息

    专利信息


    专利号:EP-2070941-A1
    优先权日:2007-12-14
    标 题 :Stereoselective synthesis of selective estrogen receptor down-regulators
    权利人:BAYER SCHERING PHARMA AG; ASTRAZENECA AB
    摘要:The present invention relates to stereoselective synthesis of 7-α-substituted estra-4-ene-3,17-diones. Such compounds are valuable intermediates in the synthesis of 7-α-substituted estra-1,3,5(10)-triene-3,17-diols. n Key step in this synthesis is reacting a 3-keto-4,6-estradiene with a Grignard reagent selected from the group consisting of a magnesium-halide alkyl halide having at least 3 carbon atoms, a magnesium-halide alkenyl halide having at least 3 carbon atoms, and a magnesium-halide alkynyl halide having at least 3 carbon atoms, in the presence of a catalyst system comprising CuI. n The obtained 7α-alkyl, alkenyl and alkynyl halides can be used for the synthesis of pharmaceutically actice 7-α-substituted estra-1,3,5(10)-triene-3,17-diols (antiestrogens).

    专利号:US-8183402-B2
    优先权日:2007-06-27
    标 题:Industrial method for the synthesis of 17-acetoxy-11β[4-(dimethylamino)-phenyl]-21-methoxy-19-norpregna-4,9-dien-3,20-dione and the key intermediates of the process
    发明人:BODI JOZSEF; VISKY GYOERGY; SZELES JANOS; MAHO SANDOR; SANTA CSABA; CSOERGEI JANOS; TUBA ZOLTAN; TERDY LASZLO; MOLNAR CSABA; ARANYI ANTAL; HORVATH ZOLTAN; BALOGH GABOR
    权利人:BODI JOZSEF; VISKY GYOERGY; SZELES JANOS; MAHO SANDOR; SANTA CSABA; CSOERGEI JANOS; TUBA ZOLTAN; TERDY LASZLO; MOLNAR CSABA; ARANYI ANTAL; HORVATH ZOLTAN; BALOGH GABOR; RICHTER GEDEON NYRT
    摘要:The present invention relates to a process for the synthesis of the 17-acetoxy-11β-[4-(dimethylamino)-phenyl]-21-methoxy-19-norpregna-4,9-dien-3,20-dione of formula (I): n nfrom 3,3-[1,2-etandiyl-bis(oxy)]-oestr-5(10),9(11)-dien-17-one of formula (II):

    专利号:US-4045452-A
    优先权日:1974-03-13
    标题 :Steroid total synthesis process utilizing a cyanoalkyl A-ring precursor
    发明人:COHEN NOAL; ROSENBERGER MICHAEL; SAUCY GABRIEL
    权利人:HOFFMANN LA ROCHE
    摘要:A multi-step, stereospecific total synthesis of steroids utilizing intermediates having a cyanoalkyl A-ring precursor is disclosed. The initial starting materials for this process are the relatively inexpensive and commercially available reagents γ-butyrolactone and sodium cyanide. The process is suitable for the preparation of racemic or optically active, medicinally valuable steroids, particularly 19-norsteroids. It is a feature of this process that conditions employed during the multiple step synthesis are selected so as to retain the normally labile nitrile group even during hydrogenation and hydrolysis steps. In this manner, it is possible to employ the nitrile group as an A-ring precursor without resorting to protective groups as wasl heretofore found necessary in previous steroid total synthesis processes.

    专利号:US-4105676-A
    优先权日:1975-12-22
    标题 :Steroid total synthesis process utilizing a cyanoalkyl a-ring precursor
    发明人:COHEN NOAL; ROSENBERGER MICHAEL; SAUCY GABRIEL
    权利人:HOFFMANN LA ROCHE
    摘要:A multi-step, stereospecific total synthesis of steroids utilizing intermediates having a cyanoalkyl A-ring precursor is disclosed. The initial starting materials for this process are the relatively inexpensive and commercially available reagents γ-butyrolactone and sodium cyanide. The process is suitable for the preparation of racemic or optically active, medicinally valuable steroids, particularly 19-norsteroids. It is a feature of this process that conditions employed during the multiple step synthesis are selected so as to retain the normally labile nitrile group even during hydrogenation and hydrolysis steps. In this manner, it is possible to employ the nitrile group as an A-ring precursor without resorting to protective groups as was heretofore found necessary in previous steroid total synthesis processes.

    专利号:US-3965138-A
    优先权日:1974-03-13
    标 题:Steroid total synthesis process utilizing a cyanoalkyl A-ring precursor
    发明人:COHEN NOAL; ROSENBERGER MICHAEL; SAUCY GABRIEL
    权利人:HOFFMANN LA ROCHE
    摘要:A multi-step, stereospecific total synthesis of steroids utilizing intermediates having a cyanoalkyl A-ring precursor is disclosed. The initial starting materials for this process are the relatively inexpensive and commercially available reagents γ-butyrolactone and sodium cyanide. The process is suitable for the preparation of racemic or optically active, medicinally valuable steroids, particularly 19-norsteroids. It is a feature of this process that conditions employed during the multiple step synthesis are selected so as to retain the normally labile nitrile group even during hydrogenation and hydrolysis steps. In this manner, it is possible to employ the nitrile group as an A-ring precursor without resorting to protective groups as was heretofore found necessary in previous steroid total synthesis processes.

    专利号:US-3991084-A
    优先权日:1970-08-26
    标题 :Steroid total synthesis process utilizing a cyanoalkyl A-ring precursor
    发明人:COHEN NOAL; ROSENBERGER MICHAEL; SAUCY GABRIEL
    权利人:HOFFMANN LA ROCHE
    摘要:A multi-step, stereospecific total synthesis of steroids utilizing intermediates having a cyanoalkyl A-ring precursor is disclosed. The initial starting materials for this process are the relatively inexpensive and commercially available reagents γ-butyrolactone and sodium cyanide. The process is suitable for the preparation of racemic or optically active, medicinally valuable steroids, particularly 19-norsteroids. It is a feature of this process that conditions employed during the multiple step synthesis are selected so as to retain the normally labile nitrile group even during hydrogenation and hydrolysis steps. In this manner, it is possible to employ the nitrile group as an A-ring precursor without resorting to protective groups as was heretofore found necessary in previous steroid total synthesis processes.
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    摘要:21 CFR Sections 1308.11-1308.15
    摘要:S109 | PARCEDC | List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 | DOI:10.5281/zenodo.10944198
    摘要:Kleemann A., Kutscher B., Reichert D., Bossart M., Pharmaceutical Substances, Thieme [Online], Stuttgart, (2025).
    参考文献:10.1016/j.jsbmb.2007.09.024
    摘要:Pinel G, Rambaud L, Cacciatore G, Bergwerff A, Elliott C, Nielen M, Le Bizec B. Elimination kinetic of 17β-estradiol 3-benzoate and 17β-nandrolone laureate ester metabolites in calves’ urine. The Journal of Steroid Biochemistry and Molecular Biology. 2008 May;110(1-2):30–8. doi: 10.1016/j.jsbmb.2007.09.024.
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