CAS: 823-36-9; 2-Ethyl-1,3-Cyclopentanedione

该化合物是一种具有分子式C7H10O2的圆形二氯酮,其特点是五人环形结构,在2号位置上以乙基组取代乙基组,该化合物具有作为有机合成中多功能中间体的活性,特别是在形成三环化合物和复杂的分子框架方面.它的二氯酮功能允许选择性地加热和凝聚反应,使其在制药和农用化学应用中具有价值.乙基基替代物可增强亲脂性,影响溶性,在不同反应条件下的再活性,通常作为具有确定纯度的晶状固体供应,确保合成工艺的一致性.

结构式图片

相似化合物

765-69-5 3883-58-7 3859-39-0

欧盟法规

REACH注册ECHA物质C&L通报REACH预注册

上下游产品

CAS号3859-39-0 2-acetylcyclope... | CAS号3859-41-4 1,3-环戊二酮 | CAS号75-07-0 乙醛 | CAS号14369-94-9 4-Oxoheptanoic ... | CAS号17082-61-0 1,2-双(三甲基硅氧基)环丁烯 | CAS号4744-10-9 丙醛缩二甲醇 | CAS号107-87-9 2-戊酮 | CAS号4505-53-7 3-ethylcyclopen... | CAS号848-04-4 乙基三烯酮 | CAS号848-01-1 (+/-)-3-Methoxy... | CAS号7443-72-3 13-乙基-3-甲氧基雌甾-1... | CAS号3625-82-9 18-methylestrad... | CAS号59949-74-5 2-ethyl-2-prop-...

合成工艺路线路线简述

  • 3859-39-0 = 823-36-9
    反应条件:1.1 Catalysts: Triethylsilane
    标题:2-Alkylcycloalkane-1,3-Diones
    参考文献:Ussr]

    3859-41-4 = 823-36-9
    反应条件:1.1 Reagents: Hantzsch Ester Catalysts: L-Proline Solvents: Dichloromethane; 1 H,Rt
    标题:Synthesis Of Highly Strained Bicyclic[3.N.1]Alkenes By A Metal-Catalyzed Conia-Ene Reaction
    作者:Kallepu,Shivakrishna; Et Al
    参考文献:Chemical Communications (Cambridge 日期:2015 卷标:51(94) 页码:16840-16843]

    17082-61-0 + 4744-08-5 = 823-36-9
    反应条件:1.1 Reagents: Boron Trifluoride Etherate Solvents: Dichloromethane2.1 Reagents: Nafion H Solvents: Trifluoroacetic Acid
    标题:An Improved Pinacol Rearrangement For The Synthesis Of 2-Alkyl-1,3-Cyclopentanediones
    作者:Martinez,Rodolfo A.; Et Al
    参考文献:Synthetic Communications 日期:1989 卷标:19(3-4) 页码:373-7]

    3859-39-0 = 823-36-9
    反应条件:1.1 Reagents: Hydrochloric Acid,Sodium Cyanoborohydride Solvents: Tetrahydrofuran,Water
    标题:An Efficient Synthesis Of Alkyl Substituted Cyclic 1,3-Diones
    作者:Pashkovsky,Felix S.; Et Al
    参考文献:Synlett 日期:2001 卷标:(9) 页码:1391-1394]

    3859-39-0 = 823-36-9
    反应条件:1.1 Reagents: Hydrochloric Acid,Sodium Cyanoborohydride Solvents: Tetrahydrofuran,Water
    标题:Selective Reduction Of The Acyl Group In Cyclic α-Acyl-β-Dicarbonyl Compounds With Sodium Cyanoborohydride. Efficient Synthesis Of Cyclic α-Alkyl-β-Dicarbonyl Compounds
    作者:Pashkovsky,F. S.; Et Al
    参考文献:Russian Chemical Bulletin (Translation Of Izvestiya Akademii Nauk 日期:2001 卷标:50(2) 页码:324-326]

    3859-41-4 = 823-36-9
    反应条件:1.1 Reagents: Hantzsch Ester Catalysts: L-Proline Solvents: Dichloromethane; 10 - 14 H,Rt
    标题:Cuh-Catalyzed Enantioselective Desymmetrization Of Cyclic 1,3-Diketones
    作者:Patil,Vaibhav B.; Et Al
    参考文献:Organic Letters 日期:2022 卷标:24(44) 页码:8233-8238]

    3859-41-4 = 823-36-9
    反应条件:1.1 Reagents: Hantzsch Ester Catalysts: L-Proline Solvents: Dichloromethane; 0.5 - 48 H,25 °C
    标题:Design,Synthesis And Application Of Spiro[4.5]Cyclohexadienones Via One-Pot Sequential P-Hydroxybenzylation/oxidative Dearomatization
    作者:Patil,Vaibhav B.; Et Al
    参考文献:Chemical Communications (Cambridge 日期:2021 卷标:57(45) 页码:5574-5577]

    3859-41-4 = 823-36-9
    反应条件:1.1 Reagents: Hantzsch Ester Catalysts: L-Proline Solvents: Ethanol; Overnight,25 °C
    标题:Stereoselective Synthesis Of Pentasubstituted 1,3-Dienes Via Ni-Catalyzed Reductive Coupling Of Unsymmetrical Internal Alkynes
    作者:Zhou,Zhijun; Et Al
    参考文献:Chemical Science 日期:2020 卷标:11(37) 页码:10204-10211]

    638-37-9 = 823-36-9
    反应条件:1.1 Reagents: Hantzsch Ester; 1 H,25 °C
    标题:Carbonyl-Assisted Reverse Regioselective Cascade Annulation Of 2-Acetylenic Ketones Triggered By Ru-Catalyzed C-H Activation
    作者:Gollapelli,Krishna Kumar; Et Al
    参考文献:Chemical Science 日期:2016 卷标:7(7) 页码:4748-4753]

    125113-33-9 = 823-36-9
    反应条件:1.1 Reagents: Nafion H Solvents: Trifluoroacetic Acid
    标题:An Improved Pinacol Rearrangement For The Synthesis Of 2-Alkyl-1,3-Cyclopentanediones
    作者:Martinez,Rodolfo A.; Et Al
    参考文献:Synthetic Communications 日期:1989 卷标:19(3-4) 页码:373-7]

    3859-41-4 = 823-36-9 + 1093646-54-8
    反应条件:1.1 Reagents: Hantzsch Ester Catalysts: L-Proline Solvents: Dichloromethane; 0.25 H,25 °C
    标题:Direct Amino Acid-Catalyzed Cascade Biomimetic Reductive Alkylations: Application To The Asymmetric Synthesis Of Hajos-Parrish Ketone Analogues
    作者:Ramachary,Dhevalapally B.; Et Al
    参考文献:Organic & Biomolecular Chemistry 日期:2008 卷标:6(22) 页码:4176-4187
3-乙基-1,2,4-环戊烷三酮 反应生成 2-乙基-1,3-环戊二酮
参考文献:Syntheses Of 1,3-Cyclopentanediones
标题:Syntheses Of 1,3-Cyclopentanediones
摘要:用已知的方法合成了 2-乙基,2-异丙基和 2-苄基-1,3-环戊二酮.2-甲基-3-氧代己二酸二乙酯在叔丁醇钾的加热下环化成 2-甲基-1,3-环戊二酮.用克莱门森法将 3-甲基-1,2,4-环戊四酮还原成 2-甲基-1,3-环戊二酮.
DOI:10.1248/cpb.13.1359

海关参考信息

专利信息


专利号:US-4110380-A
优先权日:1974-05-06
标题 :Asymmetric synthesis of organic compounds
发明人:HAJOS ZOLTAN GEORGE; PARRISH DAVID RICHARD
权利人:HOFFMANN LA ROCHE
摘要:Optically active organic compounds are prepared starting from optically inactive reactants by means of an optically active agent which influences the course of the reaction. In particular optically active compounds having a 'meso' type carbon atom undergo an intramolecular ring closure in the presence of an optically active agent to yield an optically active product having one additional ring. The present process is particularly useful in the preparation of optically active bicyclic diketones which are important intermediates in the total synthesis of steroids.

专利号:US-3962291-A
优先权日:1974-09-05
标 题:Total synthesis of 11-alkyl steroids
发明人:GARLAND ROBERT B; PAPPO RAPHAEL
权利人:SEARLE & CO
摘要:A novel total synthesis of 11-alkyl steroids, utilizing readily available and inexpensive raw materials, is described. The resulting products are useful and novel pharmacological agents possessing, for example, selective hormonal properties.

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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主要参考文献

参考标题:Synthesis Of 13-Alkyl-Gon-4-Ones
摘要:The Preparation Of 13-Methylgon-4-Enes And Novel 13-Polycarbonalkylgon-4-Enes By A New Total Synthesis Is Described. 13-Alkylgon-4-Enes Having Progestational, Anabolic And Androgenic Activities Are Prepared By Forming A Tetracylic Gonane Structure Unsaturated In The 1,3,5(10),9(11) And 14-Positions, Selectively Reducing In The B- And C-Rings, And Converting The Aromatic A-Ring Compounds So-Produced To Gon-4-Enes By Birch Reduction And Hydrolysis.

合成参考文献


摘要:Kleemann, A.; Engel, J.; Kutscher, B.; Reichert, D., Pharmaceutical Substances[Online], Thieme: Stuttgart, (2003).
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