(±)-but-3-en-2-yl 1-imidazolecarboxylate | 141037-05-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (±)-but-3-en-2-yl 1-imidazolecarboxylate
• 英文别名: 3-Buten-2-yl 1H-imidazole-1-carboxylate；but-3-en-2-yl imidazole-1-carboxylate
• CAS: 141037-05-0
• 化学式: C₈H₁₀N₂O₂
• 分子量: 166.18
• InChiKey: MIGVSMIPNMLWRT-UHFFFAOYSA-N

物化性质

• 沸点：
  247.5±33.0 °C(Predicted)
• 密度：
  1.092 g/mL at 25 °C
• 闪点：
  >110℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  4-庚醇 、 (±)-but-3-en-2-yl 1-imidazolecarboxylate 在 18-冠醚-6 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以76%的产率得到Carbonic acid 1-methyl-allyl ester 1-propyl-butyl ester
  参考文献：
  名称：

  Kryczka, Boguslaw, Bulletin des Societes Chimiques Belges, 1992, vol. 101, # 2, p. 147 - 158

  摘要：

  DOI：
• 作为产物：
  描述：

  3-丁烯-2-醇 、 N,N'-羰基二咪唑 以 1,2-二氯乙烷 为溶剂， 反应 4.0h， 生成 (±)-but-3-en-2-yl 1-imidazolecarboxylate
  参考文献：
  名称：

  通过钯催化的脱羧偶联合成烯丙基硒化物。

  摘要：

  该通讯详细介绍了钯催化的硒代碳酸酯的脱羧；手性非外消旋催化剂的使用提供了对映体富集的烯丙基硒化物，其经历了立体有规的[2,3]-σ重排以形成对映体富集的烯丙基胺和氯化物。

  DOI：

  10.1039/b806949b

文献信息

• [EN] CATALYSTS FOR THE TRANSFORMATION OF CARBON DIOXIDE AND GLYCEROL TO FORMIC ACID AND LACTIC ACID AND METHODS OF MAKING THE SAME<br/>[FR] CATALYSEURS POUR LA TRANSFORMATION DE DIOXYDE DE CARBONE ET DE GLYCÉROL EN ACIDE FORMIQUE ET EN ACIDE LACTIQUE ET LEURS PROCÉDÉS DE FABRICATION
  申请人：UNIV GEORGE WASHINGTON

  公开号：WO2018213821A1

  公开（公告）日：2018-11-22

  Catalysts and methods for transformation of glycerol and a carbon feedstock, such as CO2, a carbonate salt or a bicarbonate salt, are described herein. Homogeneous catalysts include compounds of formula M[NHC-R-linker]aLbXc, where M is a transition metal, NHC is an N-heterocyclic carbene ligand, R is an alkyl or aryl group, linker is a polar group, L is a neutral ligand, X is an anionic ligand, a ranges from 1-3, b ranges from 0-3, and c ranges from 0-3. Heterogeneous catalysts include a solid support with a catalytically active compound immobilized on the solid support, where the catalytically active compound has the formula M[NHC-R-linker]aLbXc where M is a transition metal, NHC is an N-heterocyclic carbene ligand, R is an alkyl or aryl group; linker is a polar group, L is a neutral ligand, X is an anionic ligand, a ranges from 1-3, b ranges from 0-3, and c ranges from 0-3.

  本文描述了用于转化甘油和碳原料（如CO2、碳酸盐或碳酸氢盐）的催化剂和方法。均相催化剂包括具有M[NHC-R-linker]aLbXc式化合物的化合物，其中M是过渡金属，NHC是N-杂环卡宾配体，R是烷基或芳基，linker是极性基团，L是中性配体，X是阴离子配体，a范围为1-3，b范围为0-3，c范围为0-3。非均相催化剂包括具有固体支撑物的催化活性化合物固定在固体支撑物上，其中催化活性化合物具有M[NHC-R-linker]aLbXc式化合物，其中M是过渡金属，NHC是N-杂环卡宾配体，R是烷基或芳基；linker是极性基团，L是中性配体，X是阴离子配体，a范围为1-3，b范围为0-3，c范围为0-3。
• Dual Brønsted Acid/Nucleophilic Activation of Carbonylimidazole Derivatives
  作者：Stephen T. Heller、Tingting Fu、Richmond Sarpong

  DOI：10.1021/ol300339q

  日期：2012.4.20

  Carbonylimidazole derivatives have been found to be highly active acylation reagents for esterification and amidation in the presence of pyridinium salts. These reactions are thought to involve both Bronsted acid and nucleophilic catalysis. This mode of activation has been applied to the synthesis of difficult to access oxazolidinones, as well as esters and amides. Finally, the use of pyridinium salts has been shown to accelerate the esterification of carboxylic acids with imidazole carbamates.
• Chemoselective Esterification and Amidation of Carboxylic Acids with Imidazole Carbamates and Ureas
  作者：Stephen T. Heller、Richmond Sarpong

  DOI：10.1021/ol1018882

  日期：2010.10.15

  Imidazole carbamates and ureas were found to be chemoselective esterification and amidation reagents. A wide variety of carboxylic acids were converted to their ester or amide analogues by a simple synthetic procedure in high yields
• On the reactivity of imidazole carbamates and ureas and their use as esterification and amidation reagents
  作者：Stephen T. Heller、Richmond Sarpong

  DOI：10.1016/j.tet.2011.09.057

  日期：2011.11

  The optimization, substrate scope, and mechanism of esterification and amidation of carboxylic acids mediated by imidazole-based reagents are discussed. The innate reactivity of carbonylimidazole reagents with a range of nucleophiles is also explored. New reagents developed for the synthesis of alpha,beta-unsaturated esters are described, as are reagents for the preparation of tertiary amides directly from carboxylic acids. (C) 2011 Elsevier Ltd. All rights reserved.
• CATALYSTS FOR THE TRANSFORMATION OF CARBON DIOXIDE AND GLYCEROL TO FORMIC ACID AND LACTIC ACID AND METHODS OF MAKING THE SAME
  申请人：The George Washington University

  公开号：US20200171474A1

  公开（公告）日：2020-06-04

  Catalysts and methods for transformation of glycerol and a carbon feedstock, such as CO 2 , a carbonate salt or a bicarbonate salt, are described herein. Homogeneous catalysts include compounds of formula M[NHC-R-linker]aLbXc, where M is a transition metal, NHC is an N-heterocyclic carbene ligand, R is an alkyl or aryl group, linker is a polar group, L is a neutral ligand, X is an anionic ligand, a ranges from 1-3, b ranges from 0-3, and c ranges from 0-3. Heterogeneous catalysts include a solid support with a catalytically active compound immobilized on the solid support, where the catalytically active compound has the formula M[NHC-R-linker]aLbXc where M is a transition metal, NHC is an N-heterocyclic carbene ligand, R is an alkyl or aryl group; linker is a polar group, L is a neutral ligand, X is an anionic ligand, a ranges from 1-3, b ranges from 0-3, and c ranges from 0-3.