CAS: 613-93-4; N-Methylbenzamide

该化合物是一种有机化合物,其分子式为C8H9NO,结构上来自N-甲基化的苯并胺,这种白色晶晶体固体在水中溶解程度极小,但很容易溶解于乙醇和丙酮等有机溶剂,其主要应用包括作为中间体用于制药合成和农用化学研究,因为其混合功能组是进一步化学修改的多用途建筑块. N-M乙基苯并氨在标准条件下表现出稳定性,并显示出在震动和烷基反应中的一致回动性.其定义明确的熔点(105-107°C)和纯度使得它适合实验室环境中的分析和预测性目的.

结构式图片

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

N,N-二甲基苯甲酰胺 N,N-Dimethylbenzamide 611-74-5
N-乙苯甲醯胺 N-Ethylbenzamide 614-17-5
N-苄基苯甲酰胺 N-Benzyl Benzamide 1485-70-7
苯甲酰胺 Benzamide 55-21-0
N-甲基-4-溴苯甲酰胺 4-Bromo-N-Methylbenzamide 27466-83-7
N-(2-Hydroxyethyl)-Benzamide 16405-21-3
4-Iodo-N-Methylbenzamide 89976-43-2
4-氟-N-甲基苯甲酰胺 4-Fluoro-N-Methylbenzamide 701-49-5
N-羟基-N-甲基苯甲酰胺 N-Hydroxy-N-Methylbenzamide 2446-50-6
N-丁基苯甲酰胺 N-Butylbenzamide 2782-40-3

合成工艺路线路线简述

  • 110874-21-0 = 613-93-4 + 87892-46-4
    反应条件:1.1 Reagents: Boron Trifluoride Etherate Solvents: Acetic Anhydride2.1 Reagents: Bromotrimethylsilane Solvents: Dichloromethane3.1 Reagents: Potassium Carbonate Solvents: Dichloromethane4.1 Reagents: Ammonia Solvents: Methanol
    标题:Effect Of Acyclic Pyrimidines Related To 9-[(1,3-Dihydroxy-2-Propoxy)Methyl]Guanine On Herpes Viruses
    作者:Beauchamp,Lilia M.; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:1988 卷标:31(1) 页码:144-9]

    = 613-93-4 + 87892-46-4
    反应条件:1.1 Reagents: Dimethoxymethane,Phosphorus Pentoxide Solvents: Chloroform2.1 Reagents: 15-Crown-5 Solvents: Dimethylformamide3.1 Reagents: Boron Trifluoride Etherate Solvents: Acetic Anhydride4.1 Reagents: Bromotrimethylsilane Solvents: Dichloromethane5.1 Reagents: Potassium Carbonate Solvents: Dichloromethane6.1 Reagents: Ammonia Solvents: Methanol
    标题:Effect Of Acyclic Pyrimidines Related To 9-[(1,3-Dihydroxy-2-Propoxy)Methyl]Guanine On Herpes Viruses
    作者:Beauchamp,Lilia M.; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:1988 卷标:31(1) 页码:144-9]

    103824-48-2 = 613-93-4 + 87892-46-4
    反应条件:1.1 Reagents: Ammonia Solvents: Methanol
    标题:Effect Of Acyclic Pyrimidines Related To 9-[(1,3-Dihydroxy-2-Propoxy)Methyl]Guanine On Herpes Viruses
    作者:Beauchamp,Lilia M.; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:1988 卷标:31(1) 页码:144-9]

    103824-47-1 + 20461-60-3 = 613-93-4 + 87892-46-4
    反应条件:1.1 Reagents: Potassium Carbonate Solvents: Dichloromethane2.1 Reagents: Ammonia Solvents: Methanol
    标题:Effect Of Acyclic Pyrimidines Related To 9-[(1,3-Dihydroxy-2-Propoxy)Methyl]Guanine On Herpes Viruses
    作者:Beauchamp,Lilia M.; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:1988 卷标:31(1) 页码:144-9]

    110874-22-1 = 613-93-4 + 87892-46-4
    反应条件:1.1 Reagents: Bromotrimethylsilane Solvents: Dichloromethane2.1 Reagents: Potassium Carbonate Solvents: Dichloromethane3.1 Reagents: Ammonia Solvents: Methanol
    标题:Effect Of Acyclic Pyrimidines Related To 9-[(1,3-Dihydroxy-2-Propoxy)Methyl]Guanine On Herpes Viruses
    作者:Beauchamp,Lilia M.; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:1988 卷标:31(1) 页码:144-9]

    70905-45-2 + 532-32-1 = 613-93-4 + 87892-46-4
    反应条件:1.1 Reagents: 15-Crown-5 Solvents: Dimethylformamide2.1 Reagents: Boron Trifluoride Etherate Solvents: Acetic Anhydride3.1 Reagents: Bromotrimethylsilane Solvents: Dichloromethane4.1 Reagents: Potassium Carbonate Solvents: Dichloromethane5.1 Reagents: Ammonia Solvents: Methanol
    标题:Effect Of Acyclic Pyrimidines Related To 9-[(1,3-Dihydroxy-2-Propoxy)Methyl]Guanine On Herpes Viruses
    作者:Beauchamp,Lilia M.; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:1988 卷标:31(1) 页码:144-9
马尿酸 以 丙酮 作为反应溶剂,化学反应 1.0H,以97%的收率获得产物n-甲基苯甲酰胺
参考文献:Sato,Yasuhiko; Nakai,Hideo; Mizoguchi,Tomishige,Chemical And Pharmaceutical Bulletin,1982,Vol. 30,# 4,P. 1263-1270
标题:Sato,Yasuhiko; Nakai,Hideo; Mizoguchi,Tomishige,Chemical And Pharmaceutical Bulletin,1982,Vol. 30,# 4,P. 1263-1270

海关参考信息

专利信息


专利号:US-8293930-B1
优先权日:2004-06-25
标题 :One pot synthesis of taxane derivatives and their conversion to paclitaxel and docetaxel
发明人:NAIDU RAGINA
权利人:NAIDU RAGINA; CHATHAM BIOTEC LTD
摘要:A process is provided for the semi-synthesis of taxane intermediates useful in the preparation of paclitaxel and docetaxel, in particular, the semi-synthesis of protected taxane intermediate in a one pot reaction of protecting the C-7 and C-10 positions and attaching a side chain at the C-13 position and subsequently deprotecting the group to form paclitaxel or docetaxel, and taxane intermediates.

专利号:US-7893283-B2
优先权日:2004-06-04
标题:Semi-synthesis of taxane intermediates and their conversion to paclitaxel and docetaxel
发明人:NAIDU RAGINA
权利人:CHATHAM BIOTEC LTD
摘要:A process is provided for the semi-synthesis of taxane intermediates useful in the preparation of paclitaxel and docetaxel, in particular, the semi-synthesis of protected taxane intermediates.

专利号:US-8791287-B2
优先权日:2010-07-02
标 题:Process for the synthesis of tapentadol and intermediates thereof
发明人:MOTTA GIUSEPPE; VERGANI DOMENICO; BERTOLINI GIORGIO; LANDONI NICOLA
权利人:MOTTA GIUSEPPE; VERGANI DOMENICO; BERTOLINI GIORGIO; LANDONI NICOLA; EUTICALS SPA
摘要:The object of the present invention is a new process for the synthesis of tapentadol, both as free base and in hydrochloride form, which comprises the step of alkylation of the ketone (VII) to yield the compound (VIII), as reported in Diagram 1, with high stereoselectivity due to the presence of the benzyl group as substituent of the amino group. It was surprisingly found that this substitution shifts the keto-enol equilibrium towards the desired enantiomer and amplifies the capacity of the stereocenter present in the compound (VII) to orient the nucleophilic addition of the organometallic compound at the carbonyl towards the desired stereoisomer. This substitution thus allows obtaining a considerable increase of the yields in this step, and consequently allows significantly increasing the overall yield of the entire tapentadol synthesis process. n A further object of the present invention is constituted by the tapentadol free base in solid form, obtainable by means of the process of the invention. n Still another object of the invention is represented by the crystalline forms I and II of the tapentadol free base. n A further object of the present invention is the mixture of the crystalline forms I and II of the tapentadol free base.

专利号:US-9688644-B2
优先权日:2009-04-30
标 题 :Synthesis of Tetracyclines and intermediates thereto
发明人:MYERS ANDREW G; KUMMER DAVID A; LI DERUN; HECKER EVAN; DION AMELIE; WRIGHT PETER M
权利人:HARVARD COLLEGE
摘要:The tetracycline class of antibiotics has played a major role in the treatment of infectious diseases for the past 50 years. However, the increased use of the tetracyclines in human and veterinary medicine has led to resistance among many organisms previously susceptible to tetracycline antibiotics. The recent development of a modular synthesis of tetracycline analogs through a chiral enone intermediate has allowed for the efficient synthesis of novel tetracycline analogs never prepared before. The present invention provides more efficient routes for preparing the enone intermediate and allows for substituents at positions 4a, 5, 5a, and 12a of the tetracycline ring system.

专利号:WO-2008032104-A1
优先权日:2006-09-15
标题:One pot synthesis of taxane derivatives and their conversion to paclitaxel and docetaxel
发明人:WALKER ROSS THOMSON; NAIDU RAGINA
权利人:CHATHAM BIOTEC LTD; WALKER ROSS THOMSON; NAIDU RAGINA
摘要:A process is provided for the semi-synthesis of taxane intermediates useful in the preparation of paclitaxel and docetaxel, in particular, the semi-synthesis of protected taxane intermediate in a one pot reaction, of protecting the C-10 and attaching a side chain at C-13 position and subsequently deprotecting the group to form paclitaxel or docetaxel, and intermediates used therein.

专利号:US-7202370-B2
优先权日:2003-10-27
标 题 :Semi-synthesis of taxane intermediates from 9-dihydro-13-acetylbaccatin III
发明人:NAIDU RAGINA
权利人:CONOR MEDSYSTEMS INC
摘要:A method is provided for the semi-synthesis of taxane intermediates useful in the preparation of paclitaxel and docetaxel from 9-dihydro-13-acetylbaccatin III. The preparation of a suitably protected baccatin III backbone from 9-dihydro-13-acetylbaccatin III, and the insertion of the phenylisoserine side chain onto the protected baccatin III from 9-dihydro-13-acetylbaccatin III to form the taxane derivatives, paclitaxel and docetaxel is disclosed.
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合成参考文献


摘要:Wu, X.-F., Science of Synthesis Knowledge Updates, (2014) 1, 339.
摘要:Gagnon, A.; Benoit, E.; Le Roch, A., Science of Synthesis Knowledge Updates, (2018) 4, 74.
摘要:Wu, X.-F., Science of Synthesis Knowledge Updates, (2014) 1, 302.
摘要:Glushkov, V. A.; Shklyaev, Yu. V., Science of Synthesis Knowledge Updates, (2018) 3, 249.
摘要:Glushkov, V. A.; Shklyaev, Yu. V., Science of Synthesis Knowledge Updates, (2018) 3, 251.
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