CAS: 82551-63-1; 4-Nitrobenzyl 2-Diazo-3-Oxobutanoate

该化合物是有机合成和光化应用中常用的一种 Diazo化合物,其主要优点包括它作为多用途前体在制备卡宾中发挥作用,卡宾是环丙化和C-H插入反应中有价值的中间体. 4-nitrobenzyl 组增加了有机溶剂的溶解性,同时为diazo功能提供了稳定性. 该化合物在光亲性标签和交叉连接研究中特别有用,因为它能够在紫外辐射时产生反应性物种. 它定义明确的再活性特征使得需要精确控制合成和机械研究的研究人员可以作出可靠的选择.

英文名称4-Nitrobenzyl 2-Diazo-3-Oxobutanoate
中文名称2-重氮乙酰乙酸对硝基苄酯
其它别名p-Nitrobenzyl 2-diazoacetoacetate
CAS编号82551-63-1
MFCD编号:MFCD11977231
分子式:C11H9N3O5
分子量:263.21
产品CID: 1816036
产品分类有机原料 → 重氮、偶氮或氧化偶氮化合物

相似结构搜索
InChIKey: HEKGSEIAAGMGPL-UHFFFAOYSA-N
InChI=1S/C11H9N3O5/c1-7(15)10(13-12)11(16)19-6-8-2-4-9(5-3-8)14(17)18/h2-5H,6H2,1H3…
计算化学: 氢键受体数6.0氢键供体数0.0可旋转键数5.0

MSDS等安全信息

警示词warning
危险描述H303 +H313 +H333
防范说明P264Thoroughly clean after treatmentP280Wear protective gloves/Wear protective clothing/Wear protective goggles/Wear a protective maskP305If it enters the eyesP351Rinse carefully with water for a few minutesP338Remove the contact lens(If any)And easy to operate,Continue flushingP337If eye irritation persistsP313Obtain medical advice/care
安全声明H303+H313+H333

合成工艺路线路线简述

合成目标产物 4-Nitrobenzyl 2-Diazoacetoacetate 主要起始原料 4-Nitrobenzyl Alcohol And Ethyl Diazoacetoacetate
61312-84-3 = 82551-63-1
反应条件:1.1 Reagents: Triethylamine,4-Dodecylbenzenesulfonyl Azide Solvents: Acetonitrile; Cooled; 30 Min,Cooled; 2 H,Rt
标题:The Synthesis Of Panipenem-Betamipron
作者:Wang,Qi-Jun; Et Al
参考文献:Zhejiang Huagong 日期:2010 卷标:41(1) 页码:9-14]

141-97-9 + 619-73-8 = 82551-63-1
反应条件:1.1 Solvents: Toluene; 15 H,Reflux1.2 Reagents: Triethylamine,Tosyl Azide Solvents: Acetonitrile; 0 °C; 30 Min,0 °C; 3 H,Rt
标题:Synthesis Of A Panipenem Intermediate P-Nitrobenzyl-2-Oxo-Carbapenam-3-Carboxylate
作者:Chen,Xiaofang; Et Al
参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2008 卷标:18(2) 页码:119-122]

5396-89-4 = 82551-63-1
反应条件:1.1 Reagents: Triethylamine,4-Acetamidobenzenesulfonyl Azide Solvents: Acetonitrile; 0 °C -> Rt; 2 H,Rt2.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Tetrahydrofuran; 40 - 60 Min,23 °C3.1 Reagents: Dicyclohexylcarbodiimide Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dichloromethane; 60 - 90 Min,23 °C
标题:2-Diazoacetoacetic Acid,An Efficient And Convenient Reagent For The Synthesis Of α-Diazo-β-Keto Esters
作者:Meyer,Michael E.; Et Al
参考文献:Chemical Communications (Cambridge 日期:2006 卷标:(12) 页码:1316-1318]

61312-84-3 = 82551-63-1
反应条件:1.1 Reagents: Sodium Bicarbonate,Sodium Azide Solvents: Acetone,Water; Rt1.2 Catalysts: Methanesulfonyl Chloride; Rt -> 30 °C; 2 H,30 °C; 30 °C -> 55 °C; 30 Min,55 °C; 55 °C -> Rt1.3 Reagents: Water
标题:Synthesis Of P-Nitrobenzyl 2-Diazoacetoacetate
作者:Wang,Shujuan; Et Al
参考文献:Jingxi Huagong Zhongjianti 日期:2007 卷标:37(2) 页码:37-38]

619-73-8 + 134973-72-1 = 82551-63-1
反应条件:1.1 Reagents: Dicyclohexylcarbodiimide Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dichloromethane; 60 - 90 Min,23 °C
标题:2-Diazoacetoacetic Acid,An Efficient And Convenient Reagent For The Synthesis Of α-Diazo-β-Keto Esters
作者:Meyer,Michael E.; Et Al
参考文献:Chemical Communications (Cambridge 日期:2006 卷标:(12) 页码:1316-1318]

619-73-8 + 105-45-3 = 82551-63-1
反应条件:1.1 Solvents: Toluene; 7 H,Reflux; Reflux -> 30 °C1.2 Reagents: Triethylamine,4-Dodecylbenzenesulfonyl Azide Solvents: Toluene; 1 H,25 °C
标题:Improved Synthesis Of Panipenem
作者:Fang,Huizhen; Et Al
参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2011 卷标:21(3) 页码:216-219]

941-55-9 + 61312-84-3 = 82551-63-1
反应条件:1.1 Reagents: Potassium Carbonate Catalysts: Tetrabutylammonium Chloride Solvents: Tetrahydrofuran; 2 H,Rt
标题:New Six-Membered Cyclic Nitroso Acetals - N-Silyloxy-3,6-Dihydro-2H-1,2-Oxazines: Synthesis And Studies Of The Nitrogen Inversion Process
作者:Shved,Alexander; Et Al
参考文献:European Journal Of Organic Chemistry 日期:2016 卷标:2016(33) 页码:5569-5578]

52267-50-2 = 82551-63-1
反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Tetrahydrofuran; 40 - 60 Min,23 °C2.1 Reagents: Dicyclohexylcarbodiimide Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dichloromethane; 60 - 90 Min,23 °C
标题:2-Diazoacetoacetic Acid,An Efficient And Convenient Reagent For The Synthesis Of α-Diazo-β-Keto Esters
作者:Meyer,Michael E.; Et Al
参考文献:Chemical Communications (Cambridge 日期:2006 卷标:(12) 页码:1316-1318]

555-16-8 = 82551-63-1
反应条件:1.1 Reagents: Sodium Hydroxide,Sodium Borohydride Solvents: Methanol,Water; 90 Min,35 °C2.1 Solvents: Toluene; 15 H,Reflux2.2 Reagents: Triethylamine,Tosyl Azide Solvents: Acetonitrile; 0 °C; 30 Min,0 °C; 3 H,Rt
标题:Synthesis Of A Panipenem Intermediate P-Nitrobenzyl-2-Oxo-Carbapenam-3-Carboxylate
作者:Chen,Xiaofang; Et Al
参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2008 卷标:18(2) 页码:119-122

对硝基苯甲醇置于对甲苯磺酰叠氮,三乙胺体系中,用甲苯,乙腈作为反应溶剂,化学反应 18.0H,反应生成 2-重氮乙酰乙酸对硝基苄酯
参考文献:一种制备 α-重氮乙酰乙酸酯的三甲基甲硅烷基和叔丁基二甲基甲硅烷基烯醇醚的简单方法及其在合成硫霉素类似物手性前体中的应用
标题:一种制备 α-重氮乙酰乙酸酯的三甲基甲硅烷基和叔丁基二甲基甲硅烷基烯醇醚的简单方法及其在合成硫霉素类似物手性前体中的应用
摘要:Les Enols Ethers Du Titre (A) 制备对三氟甲磺酸盐脱三烷基甲硅烷和 α-重氮乙酰乙酸盐;l'Action De L'Acetoxy-4 T-丁基二甲基甲硅烷氧基-1'Ethyl-3 Azetidinone-2 Sur Les 组成一个导管辅助 α-重氮羟基-1'Ethyl-3 Oxo-4 Azetidineacetylacetates-2
DOI:10.1139/v84-497