N-phenyl-N-hydroxybutyramide | 13663-51-9

• 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-phenyl-N-hydroxybutyramide
• 英文别名: N-Phenyl-N-butyrohydroxamsaeure；N-phenylbutanohydroxamic acid；N-hydroxy-N-phenylbutanamide
• CAS: 13663-51-9
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: ROUPGQLVDJYJAQ-UHFFFAOYSA-N

物化性质

• 熔点：
  76-77 °C(Solv: ligroine (8032-32-4))
• 沸点：
  298.7±23.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

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：
  0.3
• 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-phenyl-N-hydroxybutyramide 在 乙醇 、 ruthenium(III) trichloride hydrate 、 zinc/copper couple 作用下， 反应 4.0h， 以89%的产率得到丁酰苯胺
  参考文献：
  名称：

  Ruthenium-catalyzed reduction of N-alkoxy- and N-hydroxyamides

  摘要：

  A ruthenium-catalyzed reduction of N-alkoxy- and N-hydroxyamides was found to afford corresponding amides in good to high yields. A simple RuCl3/Zn-Cu/alcohol system, without the addition of any other ligands, exhibited a high catalytic activity, and therefore the present reaction does not require a stoichiometric amount of metals or metal complexes as reductants. When beta-substituted-alpha,beta-unsaturated N-methoxyamides were employed as substrates, concurrent hydrogenation of the olefin moiety proceeded slowly with deprotection of the methoxy group. In the reduction of N-hydroxyamides, the alcoholic solvent was found to function as a hydrogen donor. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2011.08.026
• 作为产物：
  描述：

  N-phenyl hydroxylamine hydrochloride 、 丁酰氯 在 碳酸氢钠 作用下， 以 乙醚 、 水 为溶剂， 生成 N-phenyl-N-hydroxybutyramide
  参考文献：
  名称：

  Ruthenium-catalyzed reduction of N-alkoxy- and N-hydroxyamides

  摘要：

  A ruthenium-catalyzed reduction of N-alkoxy- and N-hydroxyamides was found to afford corresponding amides in good to high yields. A simple RuCl3/Zn-Cu/alcohol system, without the addition of any other ligands, exhibited a high catalytic activity, and therefore the present reaction does not require a stoichiometric amount of metals or metal complexes as reductants. When beta-substituted-alpha,beta-unsaturated N-methoxyamides were employed as substrates, concurrent hydrogenation of the olefin moiety proceeded slowly with deprotection of the methoxy group. In the reduction of N-hydroxyamides, the alcoholic solvent was found to function as a hydrogen donor. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2011.08.026
• 作为试剂：
  描述：

  仲辛醇 在 ruthenium(III) trichloride hydrate 、 zinc/copper couple 、 N-phenyl-N-hydroxybutyramide 作用下， 反应 6.0h， 以45%的产率得到仲辛酮
  参考文献：
  名称：

  Ruthenium-catalyzed reduction of N-alkoxy- and N-hydroxyamides

  摘要：

  A ruthenium-catalyzed reduction of N-alkoxy- and N-hydroxyamides was found to afford corresponding amides in good to high yields. A simple RuCl3/Zn-Cu/alcohol system, without the addition of any other ligands, exhibited a high catalytic activity, and therefore the present reaction does not require a stoichiometric amount of metals or metal complexes as reductants. When beta-substituted-alpha,beta-unsaturated N-methoxyamides were employed as substrates, concurrent hydrogenation of the olefin moiety proceeded slowly with deprotection of the methoxy group. In the reduction of N-hydroxyamides, the alcoholic solvent was found to function as a hydrogen donor. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2011.08.026

文献信息

• Faddeeva,V.K. et al., Journal of Organic Chemistry USSR (English Translation), 1970, vol. 6, p. 276 - 280
  作者：Faddeeva,V.K. et al.

  DOI：——

  日期：——
• HARAGUCHI, KENSAKU;NISHIDA, MAMORU;AYAME, AKIMI;MUROZUMI, MASAYO;SAITOH, +, ANAL. SCI., 5,(1989) N, C. 735-738
  作者：HARAGUCHI, KENSAKU、NISHIDA, MAMORU、AYAME, AKIMI、MUROZUMI, MASAYO、SAITOH, +

  DOI：——

  日期：——
• Ruthenium-catalyzed reduction of N-alkoxy- and N-hydroxyamides
  作者：Hiroko Fukuzawa、Yasuyuki Ura、Yasutaka Kataoka

  DOI：10.1016/j.jorganchem.2011.08.026

  日期：2011.11

  A ruthenium-catalyzed reduction of N-alkoxy- and N-hydroxyamides was found to afford corresponding amides in good to high yields. A simple RuCl3/Zn-Cu/alcohol system, without the addition of any other ligands, exhibited a high catalytic activity, and therefore the present reaction does not require a stoichiometric amount of metals or metal complexes as reductants. When beta-substituted-alpha,beta-unsaturated N-methoxyamides were employed as substrates, concurrent hydrogenation of the olefin moiety proceeded slowly with deprotection of the methoxy group. In the reduction of N-hydroxyamides, the alcoholic solvent was found to function as a hydrogen donor. (C) 2011 Elsevier B.V. All rights reserved.