N-hydroxy-N-methyl-1-napthamide | 53203-13-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-hydroxy-N-methyl-1-napthamide
• 英文别名: N-Methyl-α-naphtho-hydroxamsaeure；N-hydroxy-N-methylnaphthalene-1-carboxamide
• CAS: 53203-13-7
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: QHSMCQMGIKBZAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-hydroxy-N-methyl-1-napthamide 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 N-(isopropoxymethyl)-1-napthamide
  参考文献：
  名称：

  A Facile Preparation of N-(Isopropoxyalkyl) Amides by Generation and Trapping of N-Acyliminium Ions from Ionization-Rearrangement Reactions of N-Triflyloxy Amides

  摘要：

  A series of hydroxamic acids were converted to N-triflyloxy amides which were heated in 2-propanol to give N-(1-isopropoxyalkyl) amides in high yields. The method is simple, direct, and extremely tolerant of structural diversity both in the N-acyl group, as well as in the 1-isopropoxyalkyl group. N-Alkylation of secondary N-(1-isopropoxyalkyl) amides can be used for converting them to tertiary N-(1-isopropoxyalkyl) amides. N-Acyliminium ions of wide structural diversity can be generated easily from N-(1-isopropoxyalkyl) amides available by this methodology.

  DOI：

  10.1021/jo00092a007
• 作为产物：
  描述：

  N-甲基羟胺 、 1-萘甲酰氯 生成 N-hydroxy-N-methyl-1-napthamide
  参考文献：
  名称：

  The Reaction of the Hydroxamic Acid Group in Polymer withp-Nitrophenyl Acetate

  摘要：

  通过 N-苯基丙烯酰羟肟酸乙酰基和丙烯酰胺的自由基共聚制备了含有受保护羟肟酸基团的水溶性共聚物，并用羟胺对羟肟酸基团（PHA）进行了解蔽处理。在用对硝基苯乙酸酯（1.4 v/v% CH3CN-H2O，30 °C）进行乙酰化时，PHA 单元的反应性低于相应的单体化合物。当 PHA 含量较低时（3 摩尔%），特定 PHA 阴离子（真正的反应物）的反应性在 PHA 单元解离的较大范围内保持不变（9.1 M-1 S-1）。然而，在 PHA 含量较高（11 摩尔%）的共聚物中，反应活性随着 PHA 阴离子中和的进行而降低。这一现象归因于未分离的 PHA 侧链在分子内聚集。乙酰化 PHA 单元的脱乙酰率与单体对应物的脱乙酰率相当，这与酰化过程形成鲜明对比。最后，讨论了 PHA 单元作为酯水解催化剂的可能作用。

  DOI：

  10.1246/bcsj.47.1509

文献信息

• Condition-Controlled <i>O</i>-Acylation and N–O Bond Reduction of Hydroximic Acids with Thioacetic Acid
  作者：Risong Wang、Yifei Chen、Binjie Fei、Jiahao Hu、Jianhui Chen、Yanshu Luo、Yuanzhi Xia

  DOI：10.1021/acs.orglett.3c00735

  日期：2023.5.5

  Condition-dependent transformations between hydroximic acids and thioacetic acid were achieved. Using NH4HCO3 in the ethanol solvent, efficient N–O bond cleavage of hydroxamic acids occurred to afford primary amides with high functional group compatibility. The reaction was switched to O-acylation when NEt3 and H2O were used as the base and solvent, respectively. These facile transformations could

  实现了羟肟酸和硫代乙酸之间的条件依赖性转化。在乙醇溶剂中使用 NH 4 HCO 3，异羟肟酸发生有效的 N-O 键断裂，得到具有高官能团相容性的伯酰胺。当NEt 3和H 2 O分别用作碱和溶剂时，反应切换到O-酰化。这些简单的转换可以顺利地放大到克级。初步的机理研究表明，N-O 键断裂涉及酰化/还原的级联过程。
• Hoffman Robert V., Nayyar Naresh K., J. Org. Chem, 59 (1994) N 13, S 3530-3539
  作者：Hoffman Robert V., Nayyar Naresh K.

  DOI：——

  日期：——
• A Facile Preparation of N-(Isopropoxyalkyl) Amides by Generation and Trapping of N-Acyliminium Ions from Ionization-Rearrangement Reactions of N-Triflyloxy Amides
  作者：Robert V. Hoffman、Naresh K. Nayyar

  DOI：10.1021/jo00092a007

  日期：1994.7

  A series of hydroxamic acids were converted to N-triflyloxy amides which were heated in 2-propanol to give N-(1-isopropoxyalkyl) amides in high yields. The method is simple, direct, and extremely tolerant of structural diversity both in the N-acyl group, as well as in the 1-isopropoxyalkyl group. N-Alkylation of secondary N-(1-isopropoxyalkyl) amides can be used for converting them to tertiary N-(1-isopropoxyalkyl) amides. N-Acyliminium ions of wide structural diversity can be generated easily from N-(1-isopropoxyalkyl) amides available by this methodology.
• The Reaction of the Hydroxamic Acid Group in Polymer with<i>p</i>-Nitrophenyl Acetate
  作者：Toyoki Kunitake、Yoshio Okahata、Reiko Ando

  DOI：10.1246/bcsj.47.1509

  日期：1974.6

  Water-soluble copolymers containing protected hydroxamate groups were prepared by radical copolymerization of acetyl N-phenylacrylohydroxamate and acrylamide, and the hydroxamic acid group (PHA) was unmasked by treating it with hydroxylamine. In acetylation with p-nitrophenyl acetate (1.4 v/v% CH3CN–H2O, 30 °C) the PHA unit was less reactive than the corresponding monomeric compound. When the PHA content was low (3 mol%), the reactivity of a given PHA anion (true reacting species) was invariant (9.1 M−1 S−1) over a wide range of the dissociation of the PHA unit. However, in the case of the copolymer of a higher PHA content (11 mol%) the reactivity decreased as the neutralization of the PHA anion progressed. This phenomenon was attributed to the intramolecular aggregation of the undissociated PHA side chain. The deacylation rate of the acetylated PHA unit was comparable to those of the monomeric counterparts, in contrast with the acylation process. Finally, the probable role of the PHA unit as catalyst for the ester hydrolysis was discussed.

  通过 N-苯基丙烯酰羟肟酸乙酰基和丙烯酰胺的自由基共聚制备了含有受保护羟肟酸基团的水溶性共聚物，并用羟胺对羟肟酸基团（PHA）进行了解蔽处理。在用对硝基苯乙酸酯（1.4 v/v% CH3CN-H2O，30 °C）进行乙酰化时，PHA 单元的反应性低于相应的单体化合物。当 PHA 含量较低时（3 摩尔%），特定 PHA 阴离子（真正的反应物）的反应性在 PHA 单元解离的较大范围内保持不变（9.1 M-1 S-1）。然而，在 PHA 含量较高（11 摩尔%）的共聚物中，反应活性随着 PHA 阴离子中和的进行而降低。这一现象归因于未分离的 PHA 侧链在分子内聚集。乙酰化 PHA 单元的脱乙酰率与单体对应物的脱乙酰率相当，这与酰化过程形成鲜明对比。最后，讨论了 PHA 单元作为酯水解催化剂的可能作用。