N-hydroxy-N-(naphthalene-1-yl)acetamide | 38105-20-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-hydroxy-N-(naphthalene-1-yl)acetamide
• 英文别名: N-(1-naphthyl)-aceto-hydroxamsaeure；N-Hydroxy-1-acetylaminonaphthalin；N-Hydroxy-1-acetamidonaphthalin；N-hydroxy-N-1-naphthylacetamide；N-Hydroxy-N-(naphthalen-1-yl)acetamide；N-hydroxy-N-naphthalen-1-ylacetamide
• CAS: 38105-20-3
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: GZFSUEIOINCLLZ-UHFFFAOYSA-N

物化性质

• 熔点：
  120 °C
• 沸点：
  380.4±25.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 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-(naphthalene-1-yl)acetamide 在 苯基溴化硒 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以62%的产率得到N-(4-hydroxynaphthalen-1-yl)acetamide
  参考文献：
  名称：

  Redox‐Neutral Selenium‐Catalysed Isomerisation of para ‐Hydroxamic Acids into para ‐Aminophenols

  摘要：

  AbstractA selenium‐catalysed para‐hydroxylation of N‐aryl‐hydroxamic acids is reported. Mechanistically, the reaction comprises an N−O bond cleavage and consecutive selenium‐induced [2,3]‐rearrangement to deliver para‐hydroxyaniline derivatives. The mechanism is studied through both 18O‐crossover experiments as well as quantum chemical calculations. This redox‐neutral transformation provides an unconventional synthetic approach to para‐aminophenols.

  DOI：

  10.1002/anie.202100801
• 作为产物：
  描述：

  硝基萘 在 rhodium on carbon 、 碳酸氢钠 、 一水合肼 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 N-hydroxy-N-(naphthalene-1-yl)acetamide
  参考文献：
  名称：

  Redox‐Neutral Selenium‐Catalysed Isomerisation of para ‐Hydroxamic Acids into para ‐Aminophenols

  摘要：

  AbstractA selenium‐catalysed para‐hydroxylation of N‐aryl‐hydroxamic acids is reported. Mechanistically, the reaction comprises an N−O bond cleavage and consecutive selenium‐induced [2,3]‐rearrangement to deliver para‐hydroxyaniline derivatives. The mechanism is studied through both 18O‐crossover experiments as well as quantum chemical calculations. This redox‐neutral transformation provides an unconventional synthetic approach to para‐aminophenols.

  DOI：

  10.1002/anie.202100801

文献信息

• A facile regioselective aromatic fluorination of N-aryl-N-hydroxyamides with diethylaminosulfur trifluoride (DAST)
  作者：Yasuo Kikugawa、Kazuhiro Matsumoto、Kimiyo Mitsui、Takeshi Sakamoto

  DOI：10.1039/c39920000921

  日期：——

  Treatment of N-aryl-N-hydroxyamides with diethylaminosulfur trifluoride (DAST) under conventional reaction conditions results in removal of the hydroxy function and introduction of a fluorine atom at the para position of the aromatic ring, in high yield.

  在常规反应条件下用二乙基氨基三氟化硫（DAST）处理N-芳基-N-羟基酰胺可高产率地除去羟基官能团并在芳环对位引入氟原子。
• A novel synthesis of indole derivatives by the reaction of<i>N</i>-arylhydroxamic acids with malononitrile
  作者：Yukihiko Tomioka、Kimiko Ohkubo、Hiroshi Maruoka

  DOI：10.1002/jhet.5570440222

  日期：2007.3

  An approach to indole derivatives from N-arylhydroxamic acids and malononitrile via a [3,3]-sigmatropic rearrangement and intramolecular cyclization is described. Reactions of N-arylhydroxamic acids 1a-c, 2a-c and 3a-c with malononitrile in the presence of triethylamine at room temperature gave the corresponding α-cyanoacetamide derivatives 4a-c, 5a-c, 6a-c, 7a-c and 8a-c. Thermal treatment of 4a-c

  描述了一种通过[3,3]-σ重排和分子内环化从N-芳基异羟肟酸和丙二腈中吲哚衍生物的方法。的反应Ñ -arylhydroxamic酸1A-1C，2A-C和3A-C ，在室温下三乙胺存在下丙二腈，得到相应的α氰基乙酰胺衍生物4A-C，5A-C，图6A-C，图7A-C和8a-c。用碱，例如三乙胺和甲醇钠对4a-c，5a-c和7a-c进行热处理，导致分子内环化和脱酰基，得到相应的吲哚衍生物9-11。
• The solvolysis of N-acetoxy-1-N-acetylaminonaphthalene and N-acetoxy-2-N-acetylaminonaphthalene: divergent chemistry and mutagenic activity
  作者：Graham R. Underwood、Catherine M. Davidson

  DOI：10.1039/c39850000555

  日期：——

  Upon solvolysis in neutral 40% aqueous acetone, N-acetoxy-1-N- and N-acetoxy-2-N-acetylaminonaphthalene exhibit completely different modes of reaction; the former reacts with nitrenium ion formation, while the latter undergoes acyl oxygen scission.

  在中性的40％丙酮水溶液中溶剂化时，N-乙酰氧基-1- N-和N-乙酰氧基-2- N-乙酰氨基萘显示完全不同的反应方式。前者与氮离子形成反应，而后者经历酰基氧分裂。
• [EN] NAPHTALENE AMINOALKYLENE ETHERS AND THIOETHERS, AND THEIR PHARMA CEUTICAL USES
  申请人：——

  公开号：WO1984004245A1

  公开（公告）日：1984-11-08

  (EN) A class of naphthalene aminoalkylene ether and thioether compounds exhibiting pharmacological activity including anti-secretory and anti-ulcerogenic activity, pharmaceutical compositions comprising these compounds, and methods for the treatment of gastrointestinal hyperacidity and ulcerogenic disorders in mammals using said compositions. (FR) Classe de composés thioéthers et éthers d"aminoalcènes de naphtalène possédant une activité pharmacologique, y compris une activité anti-sécrétrice et anti-ulcérogène, compositions pharmaceutiques comportant ces composés et procédés pour le traitement de l"hyperacidité gastro-intestinale et d"affections ulcérogènes chez les mammifères utilisant lesdites compositions.

  具有抗分泌和抗溃疡作用的萘胺烃基醚和硫醚类化合物及其药用组合物，以及使用这些组合物治疗哺乳动物胃肠道高酸性和溃疡性疾病的方法。
• Matsumoto, Kazuhiro; Kato, Miyako; Sakamoto, Takeshi, Journal of Chemical Research - Part S, 1995, # 1, p. 34 - 35
  作者：Matsumoto, Kazuhiro、Kato, Miyako、Sakamoto, Takeshi、Kikugawa, Yasuo

  DOI：——

  日期：——