3-methylbut-2-en-1-yl 1H-imidazole-1-carboxylate | 706810-24-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-methylbut-2-en-1-yl 1H-imidazole-1-carboxylate
• 英文别名: 3-Methylbut-2-enyl imidazole-1-carboxylate；3-methylbut-2-enyl imidazole-1-carboxylate
• CAS: 706810-24-4
• 化学式: C₉H₁₂N₂O₂
• 分子量: 180.206
• InChiKey: LNNKMMOKEWAPOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methylbut-2-en-1-yl 1H-imidazole-1-carboxylate 在 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 26.0h， 生成 N^α-benzyloxycarbonyl-N^ε-(3-methyl-2-butenyl)oxycarbonyl-L-lysine methyl ester
  参考文献：
  名称：

  Prenyl carbamates: preparation and deprotection

  摘要：

  Prenyloxycarbonylimidazole (PreocIm) and prenyl p-nitrophenyl carbonate (PreocOC(6)H(4)p-NO2), two substitutes for the unstable prenyl chloroformate, allowed an efficient introduction of the prenyloxycarbonyl group to a variety of primary and secondary amines. Deprotection of prenyl carbamates was readily achieved by, first their conversion to 2-iodo-3-methoxy-3-methylbutyl carbamates with iodine in methanol followed by reductive beta-elimination with zinc powder. These reaction conditions are compatible with the presence of a number of functional groups such as Boc and Cbz carbamates, sulfides, double bonds, indoles and aromatic ethers. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.03.028
• 作为产物：
  描述：

  N,N'-羰基二咪唑 、 异戊烯醇 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 以80%的产率得到3-methylbut-2-en-1-yl 1H-imidazole-1-carboxylate
  参考文献：
  名称：

  三氟化硼醚介导的烯丙基 1H-咪唑-1-羧酸酯对酮烯醇酯的 O-酰化一种合成取代烯醇碳酸酯的简便方法

  摘要：

  通过酮烯醇化物与烯丙基 1 H-咪唑-1-羧酸酯和三氟化硼醚合物的配合物的反应，建立了对取代烯丙醇碳酸酯的便捷获取。

  DOI：

  10.1021/jo7016313

文献信息

• The O-Acylation of Ketone Enolates by Allyl 1<i>H</i>-Imidazole-1-carboxylate Mediated with Boron Trifluoride EtherateA Convenient Procedure for the Synthesis of Substituted Allyl Enol Carbonates
  作者：Barry M. Trost、Jiayi Xu

  DOI：10.1021/jo7016313

  日期：2007.11.1

  A convenient access to substituted allyl enol carbonates was established through the reaction of ketone enolates with the complex of allyl 1H-imidazole-1-carboxylates and boron trifluoride etherate.

  通过酮烯醇化物与烯丙基 1 H-咪唑-1-羧酸酯和三氟化硼醚合物的配合物的反应，建立了对取代烯丙醇碳酸酯的便捷获取。
• Divergent Catalysis: Catalytic Asymmetric [4+2] Cycloaddition of Palladium Enolates
  作者：Kaylin N. Flesch、Alexander Q. Cusumano、Peng-Jui Chen、Christian Santiago Strong、Stephen R. Sardini、Yun E. Du、Michael D. Bartberger、William A. Goddard、Brian M. Stoltz

  DOI：10.1021/jacs.3c02104

  日期：2023.5.24

  asymmetric decarboxylative [4+2] cycloaddition from a catalytically generated chiral Pd enolate was developed, forging four contiguous stereocenters in a single transformation. This was achieved through a strategy termed divergent catalysis, wherein departure from a known catalytic cycle enables novel reactivity of a targeted intermediate prior to re-entry into the original cycle. Mechanistic studies including

  开发了一种由催化生成的手性钯烯醇化物进行的不对称脱羧[4+2]环加成反应，在一次转化中形成四个连续的立体中心。这是通过一种称为发散催化的策略实现的，其中偏离已知的催化循环使得目标中间体在重新进入原始循环之前能够产生新的反应性。包括量子力学计算、Eyring 分析和 KIE 研究在内的机理研究提供了对反应机理的深入了解。
• Prenyl carbamates: preparation and deprotection
  作者：Jean-Michel Vatèle

  DOI：10.1016/j.tet.2004.03.028

  日期：2004.5

  Prenyloxycarbonylimidazole (PreocIm) and prenyl p-nitrophenyl carbonate (PreocOC(6)H(4)p-NO2), two substitutes for the unstable prenyl chloroformate, allowed an efficient introduction of the prenyloxycarbonyl group to a variety of primary and secondary amines. Deprotection of prenyl carbamates was readily achieved by, first their conversion to 2-iodo-3-methoxy-3-methylbutyl carbamates with iodine in methanol followed by reductive beta-elimination with zinc powder. These reaction conditions are compatible with the presence of a number of functional groups such as Boc and Cbz carbamates, sulfides, double bonds, indoles and aromatic ethers. (C) 2004 Elsevier Ltd. All rights reserved.
• Copper‐Catalyzed Aerobic Oxidative Azo‐Ene Cyclization
  作者：Junsu Kim、Da Hye Lee、Jinho Kim

  DOI：10.1002/adsc.202100687

  日期：2021.10.19

  copper-catalyzed aerobic oxidative azo-ene cyclization has been developed. The developed CuI/DMAP/O2 system efficiently facilitates the aerobic oxidation of ene-containing hydrazides to azo compounds, which undergo azo-ene cyclizations for the synthesis of oxazolidinones. In addition, the present approach enables the synthesis of lactams, as well as a nitroso-ene cyclization. Preliminary mechanistic

  已开发出铜催化的有氧氧化偶氮烯环化反应。开发的CuI/DMAP/O 2系统有效地促进了含烯酰肼有氧氧化成偶氮化合物，这些化合物经历偶氮烯环化以合成恶唑烷酮。此外，本方法能够合成内酰胺以及亚硝基烯环化。初步的机理研究表明，两个羰基对于成功的偶氮-烯环化是必不可少的，并且这种偶氮-烯环化可能有一个协调的机制。