N-tert-butyl-(5-methyl-2-furfurylideneamine) N-oxide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: N-tert-butyl-(5-methyl-2-furfurylideneamine) N-oxide
• 英文别名: (Z)-N-tert-butyl-1-(5-methylfuran-2-yl)methanimine oxide；N-tert-butyl-1-(5-methylfuran-2-yl)methanimine oxide
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: ZDASELRWRHWUAL-XFFZJAGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-甲基呋喃醛 、 N-叔丁基羟胺盐酸盐 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以68%的产率得到N-tert-butyl-(5-methyl-2-furfurylideneamine) N-oxide
  参考文献：
  名称：

  摘要：

  The spin-spin coupling constants (3)J(C,H) between the hydrogen atom of the aldonitrone group and the carbon atom bound to the nitrogen atom of the N-oxide fragment were determined for a wide range of cyclic and acyclic aldonitrones. Based on comparison of these constants (trans-(3)J(C,H) (E isomer) > cis-(3)J(C,H) (Z isomer)), the Z configuration was assigned to acyclic nitrones. Coordination of organolithium compounds to the oxygen atom of the N-->O group was revealed by C-13 NMR spectroscopy. This coordination is the necessary condition for the metallation of aldonitrones. The configuration of the nitrone group is responsible for the ability of the E form of acyclic aldonitrones to undergo CD3ONa-catalyzed isotope exchange of the methine proton in CD3OD and metallation with (BuLi)-Li-s.

  DOI：

  10.1023/a:1015459811377

文献信息

• Palladium-Catalyzed Synthesis of Nitrones Via Redox Cross-Coupling of Nitro Compounds and Alcohols
  作者：Jian Xing、Hong-Yu Tang、Jing-Lin Chen、Zheng Huang、Jun-Jie Liang、Yao-Sheng Quan、Jian-Gang Mao

  DOI：10.1021/acs.joc.4c00512

  日期：2024.7.19

  methodology for the synthesis of nitrones via palladium-catalyzed redox cross-coupling of nitro compounds and alcohols is established. The protocol is a mild, convenient, ligand-free, and scalable synthesis method that can be compatible with various nitro compounds and alcohols. Nitrone is a significant multifunctional platform synthon which can be synthesized directly and efficiently via this tactic from

  建立了一种通过硝基化合物和醇的钯催化氧化还原交叉偶联合成硝酮的新方法。该方案是一种温和、方便、无配体、可扩展的合成方法，可以与各种硝基化合物和醇兼容。硝酮是一种重要的多功能平台合成子，可以通过这种策略从市售且廉价的原材料直接有效地合成。