allyl methoxycarbamate | 945743-53-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: allyl methoxycarbamate
• 英文别名: prop-2-enyl N-methoxycarbamate
• CAS: 945743-53-3
• 化学式: C₅H₉NO₃
• 分子量: 131.131
• InChiKey: ZXAKETHBNHEYML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  allyl methoxycarbamate 在 sodium hydride 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 31.0h， 生成
  参考文献：
  名称：

  Model for Antibiotic Optimization via Neoglycosylation:  Synthesis of Liponeoglycopeptides Active against VRE

  摘要：

  The neoglycosylation of a methoxyamine-appended vancomycin aglycon with all possible N'-decanoylglucopyranose and N'-biphenoylglucopyranose regioisomers led to the production of a focused set of liponeoglycopeptide variants in good yields and with excellent stereoselectivity. High-throughput antibacterial assays employing a unique set of vancomycin-resistant Enterococci faecalis and Enterococci faecium clinical isolates revealed that the nature and regiochemistry of glycosyl lipidation modulated vancomycin-resistent Enterococci potency. In contrast to prior work with lipoglycopeptides, this study reveals the glucose C3' or C4' as the optimal position for neoglycopeptide lipidation. This purely chemical method for the diversification of the glycolipid portion of lipoglycopeptide antibiotics is simple to perform on a large scale, requires minimal synthetic effort in sugar donor preparation, and provides access to highly active antibiotics that are not easily prepared by other state-of-the-art methods.

  DOI：

  10.1021/ja068602r
• 作为产物：
  描述：

  甲氧基胺盐酸盐 、 氯甲酸烯丙酯 在 碳酸氢钠 作用下， 以 四氢呋喃 、 水 、 甲醇 为溶剂， 反应 0.25h， 生成 allyl methoxycarbamate
  参考文献：
  名称：

  Model for Antibiotic Optimization via Neoglycosylation:  Synthesis of Liponeoglycopeptides Active against VRE

  摘要：

  The neoglycosylation of a methoxyamine-appended vancomycin aglycon with all possible N'-decanoylglucopyranose and N'-biphenoylglucopyranose regioisomers led to the production of a focused set of liponeoglycopeptide variants in good yields and with excellent stereoselectivity. High-throughput antibacterial assays employing a unique set of vancomycin-resistant Enterococci faecalis and Enterococci faecium clinical isolates revealed that the nature and regiochemistry of glycosyl lipidation modulated vancomycin-resistent Enterococci potency. In contrast to prior work with lipoglycopeptides, this study reveals the glucose C3' or C4' as the optimal position for neoglycopeptide lipidation. This purely chemical method for the diversification of the glycolipid portion of lipoglycopeptide antibiotics is simple to perform on a large scale, requires minimal synthetic effort in sugar donor preparation, and provides access to highly active antibiotics that are not easily prepared by other state-of-the-art methods.

  DOI：

  10.1021/ja068602r

文献信息

• Copper-catalyzed aminoalkynylation of alkenes with hypervalent iodine reagents
  作者：Kun Shen、Qiu Wang

  DOI：10.1039/c7sc03420b

  日期：——

  A copper-catalyzed aminoalkynylation of alkenes is achieved with ethynylbenziodoxolone (EBX) reagents under mild conditions with only 1 mol % copper catalyst. This transformation allows for rapid construction of diverse important azahetereocycles and installation of valuable alkyne groups in one step. The developed method features remarkable substrate scope for both terminal and internal alkenes as

  在温和条件下，仅使用 1 mol% 的铜催化剂，即可使用乙炔基苯并氧酮 (EBX) 试剂实现铜催化的烯烃氨基炔基化。这一转化允许快速构建多种重要的氮杂杂环并一步安装有价值的炔基。所开发的方法具有针对末端和内部烯烃以及不同炔基的显着底物范围，在合成、生物共轭和分子成像方面具有广泛应用的巨大潜力。
• Highly Enantioselective, Intermolecular Hydroamination of Allenyl Esters Catalyzed by Bifunctional Phosphinothioureas
  作者：Yuan-Qing Fang、Pamela M. Tadross、Eric N. Jacobsen

  DOI：10.1021/ja5117638

  日期：2014.12.31

  Bifunctional phosphinothiourea catalysts have been developed successfully for the highly regio- and enantioselective gamma-hydroamination of allenyl and propargyl esters with N-methoxy carbamate nucleophiles to yield alpha,beta-unsaturated gamma-amino acid ester products. In the case of propargyl ester substrates, the reaction proceeds through reversible phosphinothiourea-catalyzed isomerization to the corresponding allenyl ester. The high enantioselectivity of the process is attributed to a cooperative conjugate addition of a thiourea-bound carbamate anion to a vinyl phosphonium ion resulting from covalent activation of the allenyl ester substrate.