英文名称 4,4,5,5-Tetramethyl-2-(Propa-1,2-Dien-1-yl)-1,3,2-Dioxaborolane中文名称 4,4,5,5-四甲基-2-(丙1,2-二烯-1-基)-1,3,2-二氧杂硼烷IUPAC名称 4,4,5,5-tetramethyl-2-(propa-1,2-dien-1-yl)-1,3,2-dioxaborolane其它别名 2-丙二烯基-4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷; Allenylboronic Acid Pinacol EsterCAS编号 865350-17-0 MFCD编号: MFCD09265121分子式: C9H15BO2分子量: 166.03产品CID: 1867696产品分类 有机原料→分子砌块→脂肪杂环类化合物→其它脂肪杂环类化合物
相似化合物 75927-49-0 72824-05-6 83947-59-5
上下游产品 2,3-dimethyl-2,3-butane diol allenyl boronic acid propargyl bromide 2-(iodomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane p-tolyl-allyl]-morpholine4-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2-p-tolyl-allyl]-morpholine 合成工艺路线路线简述 76-09-5 + 18295-60-8 = 865350-17-0 反应条件:1.1 Reagents: Trimethyl Borate Solvents: Diethyl Ether,Toluene; 1 H,-78 °C; 1 H,0 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; 1 H,0 °C1.3 Overnight,Rt 标题:Improved Method For The Conversion Of Pinacolboronic Esters Into Trifluoroborate Salts: Facile Synthesis Of Chiral Secondary And Tertiary Trifluoroborates 作者:Bagutski,Viktor; Et Al 参考文献:Tetrahedron 日期:2009 卷标:65(48) 页码:9956-9960] 76-09-5 + 83816-41-5 = 865350-17-0 反应条件:1.1 Solvents: Diethyl Ether; 18 H,Rt1.2 Reagents: Sulfuric Acid Magnesium Salt (1:1); 30 Min,Rt 标题:Allenylboronic Acid Pinacol Ester: A Selective Partner For [4 + 2] Cycloadditions 作者:Labadie,Natalia; Et Al 参考文献:Organic Letters 日期:2021 卷标:23(13) 页码:5081-5085] 76-09-5 + 83816-41-5 = 865350-17-0 [标题:Reaction Conditions 标题:Allenylboronic Acid Pinacol Ester 作者:Silverio,Daniel L.; Et Al 参考文献:E-Eros Encyclopedia Of Reagents For Organic Synthesis 日期:2015 卷标:1 页码:1-8] 106-96-7 = 865350-17-0 反应条件:1.1 Reagents: Magnesium Catalysts: Mercuric Chloride Solvents: Diethyl Ether,Toluene; 3 - 7 °C1.2 Reagents: Trimethyl Borate Solvents: Diethyl Ether; -78 °C; 1 H,-78 °C; 30 Min,-78 °C -> 0 °C; 30 Min,0 °C1.3 Reagents: Hydrochloric Acid Solvents: Water; 0 °C; 1 H,0 °C2.1 Solvents: Diethyl Ether; 18 H,Rt2.2 Reagents: Sulfuric Acid Magnesium Salt (1:1); 30 Min,Rt 标题:Allenylboronic Acid Pinacol Ester: A Selective Partner For [4 + 2] Cycloadditions 作者:Labadie,Natalia; Et Al 参考文献:Organic Letters 日期:2021 卷标:23(13) 页码:5081-5085] 61676-62-8 = 865350-17-0 + 1337935-39-3 反应条件:1.1 Reagents: Methyllithium,Hydrochloric Acid Solvents: Diethyl Ether,Tetrahydrofuran; -78 °C2.1 Solvents: Tetrahydrofuran; -78 °C2.2 Solvents: Dimethyl Sulfoxide; 18 H,-78 °C -> Rt 标题:Silver-Catalyzed Enantioselective Propargylation Reactions Of N-Sulfonylketimines 作者:Osborne,Charlotte A.; Et Al 参考文献:Organic Letters 日期:2015 卷标:17(21) 页码:5340-5343] 76-09-5 + 18295-60-8 = 865350-17-0 反应条件:1.1 Reagents: Trimethyl Borate Solvents: Diethyl Ether; 3 H,-78 °C; 1 H,-78 °C -> 0 °C; 1 H,0 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; 1 H,0 °C1.3 Reagents: Sulfuric Acid Magnesium Salt (1:1); 14 H,Rt 标题:Catalytic Four-Component Assembly Based On Allenylboronate Platform: New Access To Privileged Allylic Amine Structures 作者:Tonogaki,Keisuke; Et Al 参考文献:Journal Of The American Chemical Society 日期:2006 卷标:128(5) 页码:1464-1465] 76-09-5 + 106-96-7 = 865350-17-0 反应条件:1.1 Reagents: Magnesium Catalysts: Mercuric Chloride Solvents: Diethyl Ether,Toluene; 3 - 7 °C1.2 Reagents: Trimethyl Borate Solvents: Diethyl Ether; -78 °C; 1 H,-78 °C; 30 Min,-78 °C -> 0 °C; 30 Min,0 °C1.3 Reagents: Hydrochloric Acid Solvents: Water; 0 °C; 1 H,0 °C1.4 Solvents: Diethyl Ether; 18 H,Rt1.5 Reagents: Sulfuric Acid Magnesium Salt (1:1); 30 Min,Rt 标题:Allenylboronic Acid Pinacol Ester: A Selective Partner For [4 + 2] Cycloadditions 作者:Labadie,Natalia; Et Al 参考文献:Organic Letters 日期:2021 卷标:23(13) 页码:5081-5085] 1337935-39-3 = 865350-17-0 反应条件:1.1 Reagents: Potassium Tert-Butoxide Solvents: N,N-Dimethylformamide-D7; 4 H,Rt 标题:Silver-Catalyzed Enantioselective Propargylation Reactions Of N-Sulfonylketimines 作者:Osborne,Charlotte A.; Et Al 参考文献:Organic Letters 日期:2015 卷标:17(21) 页码:5340-5343] 70557-99-2 + 4301-14-8 = 865350-17-0 反应条件:1.1 Solvents: Tetrahydrofuran; -78 °C1.2 Solvents: Dimethyl Sulfoxide; 18 H,-78 °C -> Rt2.1 Reagents: Potassium Tert-Butoxide Solvents: N,N-Dimethylformamide-D7; 4 H,Rt 标题:Silver-Catalyzed Enantioselective Propargylation Reactions Of N-Sulfonylketimines 作者:Osborne,Charlotte A.; Et Al 参考文献:Organic Letters 日期:2015 卷标:17(21) 页码:5340-5343] 61676-62-8 = 865350-17-0 反应条件:1.1 Reagents: Methyllithium,Hydrochloric Acid Solvents: Diethyl Ether,Tetrahydrofuran; -78 °C2.1 Solvents: Tetrahydrofuran; -78 °C2.2 Solvents: Dimethyl Sulfoxide; 18 H,-78 °C -> Rt3.1 Reagents: Potassium Tert-Butoxide Solvents: N,N-Dimethylformamide-D7; 4 H,Rt 标题:Silver-Catalyzed Enantioselective Propargylation Reactions Of N-Sulfonylketimines 作者:Osborne,Charlotte A.; Et Al 参考文献:Organic Letters 日期:2015 卷标:17(21) 页码:5340-5343] 70557-99-2 + 4301-14-8 = 865350-17-0 + 1337935-39-3 反应条件:1.1 Solvents: Tetrahydrofuran; -78 °C; -78 - -65 °C; 15 Min,-78 °C1.2 Solvents: Dimethyl Sulfoxide,Tetrahydrofuran; -78 °C; 2 - 4 H,-78 °C -> Rt; 14 H,Rt 标题:Zinc-Catalyzed Allenylations Of Aldehydes And Ketones 作者:Fandrick,Daniel R.; Et Al 参考文献:Organic Letters 日期:2011 卷标:13(20) 页码:5616-5619] 70557-99-2 + 4301-14-8 = 865350-17-0 + 1337935-39-3 反应条件:1.1 Solvents: Tetrahydrofuran; -78 °C1.2 Solvents: Dimethyl Sulfoxide; 18 H,-78 °C -> Rt 标题:Silver-Catalyzed Enantioselective Propargylation Reactions Of N-Sulfonylketimines 作者:Osborne,Charlotte A.; Et Al 参考文献:Organic Letters 日期:2015 卷标:17(21) 页码:5340-5343 4,4,5,5-Tetramethyl-2-(Prop-2-Yn-1-yl)-1,3,2-Dioxaborolane置于potassium Tert-Butylate体系中,用 N,N-二甲基甲酰胺-D7 作为反应溶剂,化学反应 4.0H,反应生成 2-丙二烯基-4,4,5,5-四甲基-1,3,2-二氧杂硼烷
参考文献:N-磺酰基酮亚胺的银催化对映选择性炔丙基化反应
标题:N-磺酰基酮亚胺的银催化对映选择性炔丙基化反应
摘要:描述了n-磺酰基酮亚胺的对映选择性银催化的炔丙基化.该反应以高收率和优异的对映体比率进行,并且与多种二芳基-和烷基酮亚胺相容.通过炔烃闭环复分解,Sonogashira交叉偶联和还原反应进行的同炔丙基产物的合成转化以高立体化学保真度进行.烯丙基和炔丙基硼烷试剂均可用于获得均炔丙基产物,其分布与涉及用硼烷试剂对银催化剂进行重金属化的机理最一致.
DOI:10.1021/acs.Orglett.5B02692
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专利信息 专利号:US-9328061-B2 优先权日:2012-03-01 标题:Simple organic molecules as catalysts for practical and efficient enantioselective synthesis of amines and alcohols 发明人:HOVEYDA AMIR H; SILVERIO DANIEL L; PILYUGINA TATIANA; TORKER SEBASTIAN; ROBBINS DANIEL 权利人:TRUSTEES BOSTON COLLEGE 摘要:The present invention provides organic molecules and methods thereof for reactions between organoboron reagents and double bonds, such as imines or carbonyls, to stereoselectively provide chiral products including amines and alcohols, entities useful for the preparation of biologically active molecules. 专利号:US-2015057451-A1 优先权日:2012-03-01 标 题 :Simple organic molecules as catalysts for practical and efficient enantioselective synthesis of amines and alcohols 专利号:WO-2013131043-A1 优先权日:2012-03-01 标 题:Simple organic molecules as catalysts for practical and efficient enantioselective synthesis of amines and alcohols全部 工厂 研发
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合成参考文献 摘要:Zhang, Q.-W.; An, K.; He, W., Science of Synthesis Knowledge Updates, (2020) 3, 37. 摘要:Okamoto, K.; Ohe, K., Science of Synthesis Knowledge Updates, (2020) 1, 33. 摘要:Cheng, Z.; Zheng, Y.; Lu, Z., Science of Synthesis: Knowledge Updates, (2023) 1, 333.