CAS: 897-06-3; Androsta-1,4-Diene-3,17-Dione

该化合物是一种血清化化合物,是合成各种药品和激素产品的关键中间体,其结构为1,4-二ene-3-one配置,特别有助于生产核聚物类固醇,代谢剂和其他生物活性类固醇.该化合物因其在化学转化中的高度反应性和选择性而受到重视,能够有效地进行下游改造.在标准条件下保持稳定,与普通有机溶剂相兼容,进一步提高其在工业和实验室环境中的效用.该中间体由于在合成途径中保持纯度和可靠性能,在研究和制造中广泛使用.

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

3-Thioxo-Androst-1,4-Dien-17-On 57334-04-0
雄烯二酮 Androstenedione 63-05-8
黄体酮 Progesterone 57-83-0
Progesterone 57-83-0
宝丹酮 1-Dehydrotestosterone 846-48-0
1-雄烯二酮 5α-Androst-1-Ene-3,17-Dione 571-40-4
去氢表雄酮 Dehydroepiandrosterone 53-43-0
睾酮 Testosterone 58-22-0
1-羟基去氢表雄酮 1α,3β-Dihydroxy-Androst-5-En-17-One 20998-18-9
孕烯醇酮醋酸酯 Pregnenolone Acetate 1778-02-5

合成工艺路线路线简述

  • 合成目标产物 Androsta-1,4-Diene-3,17-Dione 主要起始原料 5A-Androstanedione
  • 2398-63-2 = 897-06-3 [标题:Reaction Conditions
    标题:Recovery Of Androgens From Fermentation Broths By Fractional Crystallization
    参考文献:German Democratic Republic]

    846-48-0 = 897-06-3
    反应条件:1.1 Solvents: Acetone; 2 D,293 K
    标题:Method For Obtaining Androsta-1,4-Diene-3,17-Dione
    参考文献:Poland]

    = 897-06-3
    反应条件:1.1 Solvents: Methanol,Water
    标题:Microbiological Transformations. V. 1α- And 2β-Hydroxylations Of C19-Steroids
    作者:Dodson,R. M.; Goldkamp,Arthur H.; Muir,R. D.
    参考文献:Journal Of The American Chemical Society 日期:1960 卷标:82 页码:4026-33]

    57-83-0 = 897-06-3
    反应条件:1.1 Reagents: Glucose Solvents: Water; 144 H,Ph 7.8,25 °C
    标题:Enhancement Of Androstadienedione Production From Progesterone By Biotransformation Using The Hydroxypropyl-β-Cyclodextrin Complexation Technique
    作者:Manosroi,Aranya; Saowakhon,Suda; Manosroi,Jiradej
    参考文献:Journal Of Steroid Biochemistry And Molecular Biology 日期:2008 卷标:108(1-2) 页码:132-136
睾酮置于unidentified Fungal Species Isolated From Grinded Corn体系中,用 水 作为反应溶剂,化学反应 2.0H,反应生成 雄甾-1,4-二烯-3,17-二酮
参考文献:Endogenous Boldenone-Formation In Cattle: Alternative Invertebrate Organisms To Elucidate The Enzymatic Pathway And The Potential Role Of Edible Fungi On Cattle'S Feed
标题:Endogenous Boldenone-Formation In Cattle: Alternative Invertebrate Organisms To Elucidate The Enzymatic Pathway And The Potential Role Of Edible Fungi On Cattle'S Feed
摘要:Although Beta-Boldenone (Bbol) Used To Be A Marker Of Illegal Steroid Administration In Calves,Its Endogenous Formation Has Recently Been Demonstrated In These Vertebrates However,Research On The Pathway Leading To Bbol Remains Scarce This Study Shows The Usefulness Of In Vivo Invertebrate Models As Alternatives To Vertebrate Animal Experiments,Using Neomysis Integer And Lucilia Sericata. In Accordance With Vertebrates,Androstenedione (Aed) Was The Main Metabolite Of Beta-Testosterone (Bt) Produced By These Invertebrates,And Bbol Was Also Frequently Detected Moreover. In Vitro Experiments Using Feed-Borne Fungi And Microsomes Were Useful To Perform The Pathway From Bt To Bbol Even The Conversion Of Phytosterols Into Steroids Was Shown In Vitro Both In Vivo And In Vitro. The Conversion Of Bt Into Bbol Could Be Demonstrated In This Study. Metabolism Of Phytosterols By Feed-Borne Fungi May Be Of Particular Importance To Explain The Endogenous Bbol-Formation By Cattle To The Best Of Our Knowledge,It Is The First Time The Latter Pathway Is Described In Literature (C) 2010 Elsevier Ltd All Rights Reserved
DOI:10.1016/j.Jsbmb.2010.02.020

海关参考信息

专利信息


专利号:WO-0200681-A1
优先权日:2000-06-27
标题 :20-fluoro-17(20)-vinyl steroids as inhibitors of c17-20-lyase and 5-alpha reductase
发明人:PEET NORTON P; WEINTRAUB PHILIP M; BURKHART JOSEPH P; GATES CYNTHIA A
权利人:AVENTIS PHARMA INC; PEET NORTON P; WEINTRAUB PHILIP M; BURKHART JOSEPH P; GATES CYNTHIA A
摘要:The invention related to 20κ-fluoropregna-4,17(20)-dien-3-on-21-oic acid ethyl ester, 20κ-fluoro-3β-hydroxypregna-4,17(20)-dien-21-oic acid ethyl ester, 20κ-fluoro-21-hydroxypregna-4,17(20)-dien-3-one, 20κ-fluoropregna-4,17(20)-dien-3β,21-diol and related compounds and to compositions incorporating these compounds, as well as the inhibition of C17,20 lyase, 5α-reductase and C17-hydroxylase, and to the use of these compounds in the treatment of androgen and estrogen mediated or dependent disorders, including benign prostatic hyperplasia, prostate cancer, breast cancer and DHT-mediated disorders such as acne and hirsutism. Treatment of disorders related to the over synthesis of cortisol, for example, Cushing's Syndrome are also included. The treatment of androgen-dependent disorders also includes a combination therapy with known androgen-receptor antagonists, such as flutamide. The compounds of the invention have general formulae (I).

专利号:US-7846874-B2
优先权日:2004-03-23
标 题 :Method for the identification of a metabolic pathway family by means of positive selection
发明人:MONSAN PIERRE; BENSOUSSAN CLAUDE; REULET PHILIPPE; NALIN RENAUD; ROBE PATRICK; TUPHILE KARINE; GILLET BENJAMIN; PUJIC PIERRE
权利人:LIBRAGEN
摘要:The invention relates to the direct selection of metabolic pathways having a determined function in the transformation of a substrate {Ai} into a target product {B}, which is of interest in the industrial, pharmaceutical or agri-food sectors. More specifically, the invention relates to the detection, within metagenomic libraries, of novel biosynthesis pathways involved in a biochemical reaction having a known product {B}. The selection and characterization of said novel metabolic pathways enables {B} to be produced enzymatically. The invention provides an alternative to the chemical synthesis of the molecule in question {B}. Moreover, and above all, the invention can be used specifically to target and exploit the only metabolic pathways enabling the transformation of {Ai} into {B}, while eliminating the associated metabolic pathways that can catabolise the target product {B}.

专利号:US-9090545-B2
优先权日:2011-10-14
标 题 :Asymmetric synthesis of organic compounds
发明人:FLETCHER STEPHEN P; MAKSYMOWICZ REBECCA M; ROTH PHILIPPE M C
权利人:ISIS INNOVATION
摘要:The present invention provides processes for the production of chiral compounds in a stereoisomeric excess. The present processes involve reacting a hydrometallated alkene compound with a compound comprising a conjugated-bond system under conditions such that the compounds undergo an asymmetric 1,4- or 1,6-conjugate addition reaction, generating a chiral compound in a stereoisomeric excess. The reaction is performed in the presence of a metal catalyst, which catalyst preferably comprises a non-racemic chiral ligand.

专利号:US-4474701-A
优先权日:1983-03-10
标题 :Process for the separation of 4-androsten-3,17-dione and 1,4-androstadien-3,17-dione
发明人:TEICHMUELLER GERHARD; RABE JOACHIM; HENKEL HARRY
权利人:JENAPHARM VEB
摘要:A process is disclosed for the separation of 4-androsten-3,17-dione/1,4-androstadien-3,17-dione mixtures, which are produced, e.g., upon microbiological sterol-side chain decomposition, through conversion of said mixture into a mixture of 17β-cyano-17α-hydroxy-4-androsten-3-one/17β-cyano-17.alpha.-hydroxy-1,4-androstadien-3-one, from which the difficultly soluble 17β-cyano-17α-hydroxy-4-androsten-3-one is separated in crystalline form through filtration, and the 17β-cyano-17α-hydroxy-1,4-androstadiene remaining in the mother liquor is re-split, directly or after extraction with organic solvent, by treatment in alkaline medium, into 1,4-androstadien-3,17-dione, and isolated as such. The separation of the products follows in high yields, and in sufficient purity for further working-up in the synthesis of androstane and pregnane derivatives, as well as estratrienes.

专利号:US-5166055-A
优先权日:1987-12-23
标 题:Microbiological preparation of 9-alpha-hydroxy-17-keto steroids
发明人:SLIJKHUIS HARMEN; MARX ARTHUR F
权利人:GIST BROCADES NV
摘要:9 alpha -hydroxy-17-keto steroids are prepared by fermenting steroids having a C-17-side chain of 5-10 carbon atoms inclusive, with the novel Mycobacterium species CBS 482.86. Starting from various substrates containing a 5-10 C carbon chain on C-17, 9 alpha -hydroxyandrost-4-ene-3,17-dione, 7 alpha ,9 alpha ,12 alpha -trihydroxyandrost-4-ene-3,17-dione or 9 alpha -hydroxyandrost-4,11-diene-3,17-dione is obtained in high yield. The resulting compounds are useful intermediates in the synthesis of therapeutically important steroids, particularly corticosteroids.

专利号:US-5298398-A
优先权日:1987-12-23
标题 :Preparation of 9-α-hydroxy-17-keto steroids using Mycobacterium species CBS 482.86
发明人:SLIJKHUIS HARMEN; MARX ARTHUR F
权利人:GIST BROCADES NV
摘要:9 alpha -hydroxy-17-keto steroids are prepared by fermenting steroids having a C-17-side chain of 5-10 carbon atoms inclusive, with the novel Mycobacterium species CBS 482.86. Starting from various substrates containing a 5-10 C carbon chain on C-17, 9 alpha -hydroxyandrost-4-ene-3,17-dione, 7 alpha ,9 alpha ,12 alpha -trihydroxyandrost-4-ene-3,17-dione or 9 alpha -hydroxyandrost-4,11-diene-3,17-dione is obtained in high yield. The resulting compounds are useful intermediates in the synthesis of therapeutically important steroids, particularly corticosteroids.
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合成参考文献


摘要:Takeda, T.; Tsubouchi, A., Science of Synthesis, (2010) 47, 258.
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:S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664
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