CAS: 869856-07-5; (S)-(3,4-Dimethoxybicyclo[4.2.0]Octa-1,3,5-Trien-7-yl)Methanamine

英文名称(S)-(3,4-Dimethoxybicyclo[4.2.0]Octa-1,3,5-Trien-7-yl)Methanamine
中文名称(S)-(3,4-二甲氧基双环[4.2.0]辛-1,3,5-三烯-7-基)甲胺
IUPAC名称(S)-(3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methanamine
其它别名(1S)-4,5-二甲氧基-1-(氨基甲基)苯并环丁烷; (7S)-3,4-Dimethoxybicyclo[4.2.0]Octa-1,3,5-Triene-7-Methanamine
CAS编号869856-07-5
MFCD编号:MFCD09264095
FDA UNII编号:7E4EZC4U3F
分子式:C11H15NO2分子量:193.25
产品CID: 1873868
产品分类有机原料→分子砌块→芳环类化合物→苯类化合物

相似结构搜索
InChIKey: JDZSBHBIJDIACW-MRVPVSSYSA-N
InChI=1S/C11H15NO2/c1-13-10-4-7-3-8(6-12)9(7)5-11(10)14-2/h4-5,8H,3,6,12H2,1-2H3/t8-/m1/s1
计算化学: 氢键受体数3.0氢键供体数1可旋转键数3

MSDS等安全信息

GHS符号GHS05,GHS07
警示词Danger
危险描述H315-H318-H335
防范说明P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501
危险等级8
UN编号3259.0
包装等级Ⅲ

上下游产品

DBC (+/-)-(3,4-dimethoxybicyclo[4.2.0]°Cta-1,3,5-trien-7-yl)methylamine

合成工艺路线路线简述

35202-54-1 = 869856-07-5
反应条件:1.1 Reagents: Hydrogen,Ammonium Hydroxide Catalysts: Nickel Solvents: Ethanol,Water; 12 H,50 °C2.1 Solvents: Ethanol,Water; 1 H,Reflux; Reflux -> Rt; Overnight,Rt3.1 Reagents: Sodium Hydroxide
标题:Improved Synthesis Of Ivabradine
作者:Ye,Xiaojuan; Et Al
参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2010 卷标:20(2) 页码:106-109]

41234-20-2 = 869856-07-5
反应条件:1.1 Solvents: Dimethylformamide2.1 Reagents: Ammonia,Sodium Amide; 1 H,-60 °C; -60 °C -> -70 °C2.2 -70 °C; 3 H,-70 °C2.3 Reagents: Ammonium Chloride; -70 °C; Overnight,Rt3.1 Reagents: Hydrogen,Ammonium Hydroxide Catalysts: Nickel Solvents: Ethanol,Water; 12 H,50 °C4.1 Solvents: Ethanol,Water; 1 H,Reflux; Reflux -> Rt; Overnight,Rt5.1 Reagents: Sodium Hydroxide
标题:Improved Synthesis Of Ivabradine
作者:Ye,Xiaojuan; Et Al
参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2010 卷标:20(2) 页码:106-109]

41234-19-9 = 869856-07-5
反应条件:1.1 Reagents: Sodium Bicarbonate,Sodium Borohydride2.1 Solvents: Dimethylformamide3.1 Reagents: Ammonia,Sodium Amide; 1 H,-60 °C; -60 °C -> -70 °C3.2 -70 °C; 3 H,-70 °C3.3 Reagents: Ammonium Chloride; -70 °C; Overnight,Rt4.1 Reagents: Hydrogen,Ammonium Hydroxide Catalysts: Nickel Solvents: Ethanol,Water; 12 H,50 °C5.1 Solvents: Ethanol,Water; 1 H,Reflux; Reflux -> Rt; Overnight,Rt6.1 Reagents: Sodium Hydroxide
标题:Improved Synthesis Of Ivabradine
作者:Ye,Xiaojuan; Et Al
参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2010 卷标:20(2) 页码:106-109]

5392-10-9 = 869856-07-5
反应条件:1.1 Reagents: Pyridine,Ammonium Formate Solvents: Ethanol,Toluene; Rt -> 120 °C; 8 H,120 °C; 2 H,0 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; Acidified2.1 Reagents: Sodium Bicarbonate,Sodium Borohydride3.1 Solvents: Dimethylformamide4.1 Reagents: Ammonia,Sodium Amide; 1 H,-60 °C; -60 °C -> -70 °C4.2 -70 °C; 3 H,-70 °C4.3 Reagents: Ammonium Chloride; -70 °C; Overnight,Rt5.1 Reagents: Hydrogen,Ammonium Hydroxide Catalysts: Nickel Solvents: Ethanol,Water; 12 H,50 °C6.1 Solvents: Ethanol,Water; 1 H,Reflux; Reflux -> Rt; Overnight,Rt7.1 Reagents: Sodium Hydroxide
标题:Improved Synthesis Of Ivabradine
作者:Ye,Xiaojuan; Et Al
参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2010 卷标:20(2) 页码:106-109]

120-14-9 = 869856-07-5
反应条件:1.1 Reagents: Bromine Solvents: Methanol; Rt; 24 H,Rt1.2 Reagents: Water2.1 Reagents: Pyridine,Ammonium Formate Solvents: Ethanol,Toluene; Rt -> 120 °C; 8 H,120 °C; 2 H,0 °C2.2 Reagents: Hydrochloric Acid Solvents: Water; Acidified3.1 Reagents: Sodium Bicarbonate,Sodium Borohydride4.1 Solvents: Dimethylformamide5.1 Reagents: Ammonia,Sodium Amide; 1 H,-60 °C; -60 °C -> -70 °C5.2 -70 °C; 3 H,-70 °C5.3 Reagents: Ammonium Chloride; -70 °C; Overnight,Rt6.1 Reagents: Hydrogen,Ammonium Hydroxide Catalysts: Nickel Solvents: Ethanol,Water; 12 H,50 °C7.1 Solvents: Ethanol,Water; 1 H,Reflux; Reflux -> Rt; Overnight,Rt8.1 Reagents: Sodium Hydroxide
标题:Improved Synthesis Of Ivabradine
作者:Ye,Xiaojuan; Et Al
参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2010 卷标:20(2) 页码:106-109]

869856-07-5 + 1188-37-0 = 869856-07-5
反应条件:1.1 Reagents: Sodium Hydroxide
标题:Improved Synthesis Of Ivabradine
作者:Ye,Xiaojuan; Et Al
参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2010 卷标:20(2) 页码:106-109]

1232191-58-0 = 869856-07-5
反应条件:1.1 Reagents: Isopropylamine Catalysts: Omega Transaminase Solvents: Dimethyl Sulfoxide,Water; 8 H,Ph 7.5,30 °C1.2 Solvents: Ethyl Acetate1.3 Reagents: Sodium Hydroxide Solvents: Water; Ph 12,0 °C
标题:Exploiting The Biocatalytic Toolbox For The Asymmetric Synthesis Of The Heart-Rate Reducing Agent Ivabradine
作者:Pedragosa-Moreau,Sandrine; Et Al
参考文献:Advanced Synthesis & Catalysis 日期:2017 卷标:359(3) 页码:485-493]

1188-37-0 + 73344-75-9 = 869856-07-5
反应条件:1.1 Solvents: Ethanol,Water; 1 H,Reflux; Reflux -> Rt; Overnight,Rt2.1 Reagents: Sodium Hydroxide
标题:Improved Synthesis Of Ivabradine
作者:Ye,Xiaojuan; Et Al
参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2010 卷标:20(2) 页码:106-109]

35249-62-8 = 869856-07-5
反应条件:1.1 Reagents: Ammonia,Sodium Amide; 1 H,-60 °C; -60 °C -> -70 °C1.2 -70 °C; 3 H,-70 °C1.3 Reagents: Ammonium Chloride; -70 °C; Overnight,Rt2.1 Reagents: Hydrogen,Ammonium Hydroxide Catalysts: Nickel Solvents: Ethanol,Water; 12 H,50 °C3.1 Solvents: Ethanol,Water; 1 H,Reflux; Reflux -> Rt; Overnight,Rt4.1 Reagents: Sodium Hydroxide
标题:Improved Synthesis Of Ivabradine
作者:Ye,Xiaojuan; Et Al
参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2010 卷标:20(2) 页码:106-109

📜(R,S)-3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-Triene-7-Carbaldehyde置于ω-Transaminase Ata-P1A06,异丙胺体系中,用 Aq. Phosphate Buffer,二甲基亚砜作为反应溶剂,化学反应 8.0H,以85%的收率获得产物(1S)-4,5-二甲氧基-1-(氨基甲基)苯并环丁烷
参考文献:开发用于心率降低剂伊伐布雷定的不对称合成的生物催化工具箱
标题:开发用于心率降低剂伊伐布雷定的不对称合成的生物催化工具箱
摘要:已经评估了几种化学酶促途径来生产心律降低剂伊伐布雷定.脂肪酶和ω-转氨酶已被确认为制备关键对映体纯前体的有用生物催化剂.外消旋伯胺的烷氧基羰基化反应经脂肪酶催化的动力学拆分,随后对所得氨基甲酸酯进行化学还原,得到了n-甲基化(S)-胺,距离伊伐布雷定一步之遥.或者,通过醛前体的不对称生物胺化进行动态动力学拆分,可按四步顺序以50%的总收率制备对映体纯的伊伐布雷定的规模规模合成.
DOI:10.1002/adsc.201601222

海关参考信息

2902600000-乙苯
2902700000-异丙基苯
2905110000-甲醇
2907210001-间苯二酚
💡 提示：海关信息按照顺序优先匹配，如需确认的海关信息，请参考相关资料。
详情请参考：📖 海关编码查询和海关进出口税则

专利信息

专利号:US-9506095-B2
优先权日:2012-02-09
标题:Process for the enzymatic synthesis of (7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carboxylic acid or esters thereof, and application in the synthesis of ivabradine and salts thereof
发明人：PEDRAGOSA-MOREAU SANDRINE; LEFOULON FRANÃ‡OIS
权利人:SERVIER LAB; LES LABORATORIES SERVIER
摘要:Process for the enzymatic synthesis of the compound of formula (I): n nwherein R 1 represents a hydrogen atom or an alkyl group.n n Application in the synthesis of ivabradine and addition salts thereof with a pharmaceutically acceptable acid.

专利号:US-6982350-B2
优先权日:2004-05-19
标题:Process for the synthesis of (1S)-4,5-dimethoxy-1-(methylaminomethyl)-benzocyclobutane and addition salts thereof, and to the application thereof in the synthesis of ivabradine and addition salts thereof with a pharmaceutically acceptable acid
发明人：LERESTIF JEAN-MICHEL; GONZALEZ BLANCO ISAAC; LECOUVE JEAN-PIERRE; BRIGOT DANIEL
权利人:SERVIER LAB
摘要:Process for the synthesis of the compound of formula (I): n n Application in the synthesis of ivabradine, addition salts thereof with a pharmaceutically acceptable acid, and hydrates thereof.

专利号:US-8101747-B2
优先权日:2009-03-31
标题:Process for the synthesis of ivabradine and addition salts thereof with a pharmaceutically acceptable acid
发明人：PEGLION JEAN-LOUIS; DESSINGES AIMEE; SERKIZ BERNARD
权利人:PEGLION JEAN-LOUIS; DESSINGES AIMEE; SERKIZ BERNARD; SERVIER LAB
摘要:Process for the synthesis of ivabradine of formula (I): n nand addition salts thereof with a pharmaceutically acceptable acid.

专利号:US-8927758-B2
优先权日:2008-08-29
标题:Process for the resolution of enantiomers of (3,4 dimethoxy-bicyclo[4.2.0]octa-1,3,5-trien-7-yl)nitrile and application in the synthesis of ivabradine
发明人：LERESTIF JEAN-MICHEL; LECOUVE JEAN-PIERRE; DRON DANIEL; GOJON ERIC; PHAN MARYSE
权利人:SERVIER LAB; SERVIER LAB
摘要:Process for the optical resolution of the compound of formula (I): n nby chiral chromatography.n n Application in the synthesis of ivabradine, of its addition salts with a pharmaceutically acceptable acid and of their hydrates.

专利号:BR-PI0500480-B1
优先权日:2004-05-19
标题 :PROCESS FOR THE SYNTHESIS OF IVABRADINE AS WELL AS PROCESSES FOR THE RESOLUTION OF AMINE AND FOR THE SYNTHESIS OF COMPOUND RELATED TO THE SYNTHESIS OF IVABRADINE

专利号:US-2005261376-A1
优先权日:2004-05-19
标题:Process for the synthesis of (is)-4,5-dimethoxy-1-(methylaminomethyl)-benzocyclobutane and addition salts thereof, and to the application thereof in the synthesis of ivabradine and addition salts thereof with a pharmaceutically acceptable acid

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主要参考文献

参考标题:Process For The Resolution Of Enantiomers Of (3,4-Dimethoxy-Bicyclo[4.2.0]Octa-1,3,5-Trien-7-Yl) Nitrile And Application In The Synthesis Of Ivabradine
摘要:Process For The Optical Resolution Of The Compound Of Formula (I): By Chiral Chromatography. Application In The Synthesis Of Ivabradine, Of Its Addition Salts With A Pharmaceutically Acceptable Acid And Of Their Hydrates.