CAS: 2390-99-0; Chanoclavine

该化合物是一个复杂的有机化合物,具有独特的结构特征,含有一种2-en-1-ol-阳性,表明存在一种烷基和酒精功能组,有助于其再活性和潜在的生物活动;该化合物还具有四氢苯甲[cd]元素结构,这表明该物质可能与生物系统发生相互作用,特别是在药理学方面.

结构式图片

MSDS等安全信息

    合成工艺路线路线简述

    • 合成目标产物 Chanoclavine 主要起始原料 Carbamic Acid, [1,3,4,5-Tetrahydro-5-(3-Hydroxy-2-Methyl-1-Propenyl)Benz[cd]Indol-4-Yl]-, Methyl Ester, [4R-[4α,5β(E)]]- (9CI)
    • (文献来源)合成步骤主要原料 Carbamic Acid, [1,3,4,5-Tetrahydro-5-(3-Hydroxy-2-Methyl-1-Propenyl)Benz[cd]Indol-4-Yl]-, Methyl Ester, [4R-[4α,5β(E)]]- (9Ci)
    📜4-吲哚甲醛置于盐酸,4-二甲氨基吡啶,Palladium Diacetate,Sodium Tetrahydroborate,Sodium Periodate,四氧化锇,Lithium Aluminium Tetrahydride,水,二异丁基氢化铝,Potassium Carbonate,N-甲基吗啉氧化物,R-(+)-1,1'-联萘-2,2'-双二苯膦,三乙胺,汞,三氟乙酸,锌体系中,用 四氢呋喃,甲醇,乙醚,二氯甲烷,丙酮,乙腈 用作溶剂,化学反应 90.58H,反应生成裸麦角碱
    参考文献:Synthesis Of (−)-Chanoclavine I
    标题:Synthesis Of (−)-Chanoclavine I
    摘要:The Total Enantioselective Synthesis Of (-)-Chanoclavine I 2 In Twelve Steps From Indole-4-Carboxaldehyde 4 Is Described The Key-Step 3--> 6 Which Involves The Formation Of The C Ring By Creation Of The C5-C10 Bond Is Catalyzed By A Chiral Palladium (0) Complexes. The Chiral Ergoline Synthon 6 Is Produced With An Excellent Diastereo-And Enantioselectivity (Up To 95%) Eel.
    Doi:10.1016/0957-4166(94)80122-3

    海关参考信息

    专利信息


    专利号:US-3929796-A
    优先权日:1974-08-02
    标 题:Synthesis of penniclavine and elymoclavine
    发明人:KORNFELD EDMUND C; BACH NICHOLAS J
    权利人:LILLY CO ELI
    摘要:Synthesis of penniclavine and of elymoclavine, intermediates useful therein, and novel compounds producible therefrom.

    专利号:US-3968112-A
    优先权日:1974-08-02
    标 题:Synthesis of penniclavine and elymoclavine
    发明人:KORNFELD EDMUND C; BACH NICHOLAS J
    权利人:LILLY CO ELI
    摘要:Synthesis of penniclavine and of elymoclavine, intermediates useful therein, and novel compounds producible therefrom.

    专利号:US-3923812-A
    优先权日:1974-08-02
    标题:Synthesis of elymoclavine
    发明人:BACH NICHOLAS J; KORNFELD EDMUND C
    权利人:LILLY CO ELI
    摘要:Elymoclavine is prepared by oxidation of D-6-methyl-8hydroxymethyl-10 Alpha -methoxy-8-ergolene to the corresponding D-8-aldehyde followed by reduction with an active metal in acid medium.

    专利号:US-4054567-A
    优先权日:1975-08-11
    标 题:6-Methyl-8β-hydroxymethyl-8-γ-substituted-9-ergolene compounds
    发明人:KORNFELD EDMUND C; BACH NICHOLAS J
    权利人:LILLY CO ELI
    摘要:Synthesis of penniclavine and of elymoclavine, intermediates useful therein, and novel compounds producible therefrom.

    专利号:CA-1051879-A
    优先权日:1974-08-02
    标题 :Synthesis of elymoclavine and derivatives

    专利号:CA-1042423-A
    优先权日:1974-08-02
    标题 :Synthesis of penniclavine and derivatives

    供应商参考报价(招募中)

    品牌试剂参考报价(招募中)

    📌 第三方产品分析报告

    ✅ COA系统入驻 | 共享模式

    主要参考文献

    参考标题:Total Synthesis Of Optically Active Chanoclavine-I
    作者:Yuusaku Yokoyama,Kazuhiro Kondo,Masako Mitsuhashi,Yasuoki Murakami |发布日期:1996.12
    摘要:The Total Synthesis Of Optically Active Chanoclavine-I, An Ergot Alkaloid, Was Accomplished Using Palladium-Catalyzed Intramolecular Cyclization (Heck Reaction) As A Key Step. The Conjugate Ester (6) Was Obtained In 2 Steps From Optically Active 4-Bromotryptophan (10), And The Cyclization Of 6 Proceeded Smoothly Without Racemization To Give The Key Intermediate, Tricyclic Tetrahydrobenz[c,D]Indole

    合成参考文献


    摘要:Zhang, X.; You, S.-L., Science of Synthesis: Metal-Catalyzed Cyclization Reactions, (2016) 1, 105.
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