N-phenylacetyl-N-tert-butylhydroxylamine | 68872-03-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-phenylacetyl-N-tert-butylhydroxylamine
• 英文别名: N-hydroxy-N-tert-butylphenylacetamide；phenyl-acetic acid-(hydroxy-tert-butylamide)；Phenyl-essigsaeure-(hydroxy-tert-butylamid)；N-Phenylacetyl-N-tert-butylhydroxylamin；N-tert-butyl-N-hydroxy-2-phenylacetamide
• CAS: 68872-03-7
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: XJYRQMVIQOUSDK-UHFFFAOYSA-N

物化性质

• 沸点：
  328.8±35.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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-phenylacetyl-N-tert-butylhydroxylamine 在 三乙胺 、 乙腈 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 N-tert-butyl-2-hydroxy-2-phenylacetamide
  参考文献：
  名称：

  Base-promoted reaction of O-sulfonylated hydroxamic acids with nucleophiles. A new method for the synthesis of .alpha.-substituted amides

  摘要：

  Treatment of a series of hydroxamic acids 2 with mesyl chloride in the presence of 2 equiv of triethylamine at 0-degrees-C gives 2-chloroamides 3 in good yields. Use of a single equivalent of triethylamine gives the (N-mesyl-oxy)amides 1, which are versatile synthetic intermediates as they can be readily converted to 2-bromoamides 4 with lithium bromide and triethylamine and to 2-hydroxyamides 5 with triethylamine in aqueous acetonitrile.

  DOI：

  10.1021/jo00047a024
• 作为产物：
  描述：

  [Tert-butyl-(2-phenylacetyl)amino] 2-phenylacetate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以62%的产率得到N-phenylacetyl-N-tert-butylhydroxylamine
  参考文献：
  名称：

  Anionic Hetero[3,3] and [3,5] Rearrangements of Hydroxylamine Derivatives Accompanied with N-O Bond Cleavage

  摘要：

  由羟胺衍生物就地生成的芳香族和脂肪族N,O-双乙烯基羟胺体系能顺利进行[3,3]重排反应。碱催化形成的烯醇盐或双烯醇盐的N-芳基-O-酰基羟胺、N,O-双酰基羟胺和N-酰基羟胺-O-氨基甲酸酯，能够在N-O键断裂的同时形成C-C或C-N键。

  DOI：

  10.1055/s-1994-25645

文献信息

• Formation of aziridinones (α-lactams) from hydroxamic derivatives
  作者：Christine M. Bladon、Gordon W. Kirby

  DOI：10.1039/c39820001402

  日期：——

  Various NO-disubstituted derivatives of chloroaceto- and phenylaceto-hydroxamic acid are shown to cyclise with base to give aziridinones with cleavage of the N–O bond, a process exemplified by an efficient synthesis of 1-t-buty-3-phenylaziridin-2-one.

  氯乙酰乙酸和苯基乙酰氧肟酸的各种NO-二取代衍生物已显示与碱环化，生成带有N-O键断裂的叠氮基吡啶酮，该过程以1-t-buty-3-phenylaziridin-2的有效合成为例。 -一。
• Behrens et al., Journal of Biological Chemistry, 1948, vol. 175, p. 771,778
  作者：Behrens et al.

  DOI：——

  日期：——
• Alewood,P.F. et al., Journal of the Chemical Society. Perkin transactions I, 1978, p. 1066 - 1076
  作者：Alewood,P.F. et al.

  DOI：——

  日期：——
• Efficient conversion of O-sulfonylated arylacetohydroxamic acids to 2-substituted secondary amides
  作者：Robert V. Hoffman、Naresh K. Nayyar、Bruce W. Klinekole

  DOI：10.1021/ja00041a064

  日期：1992.7
• Base-promoted reaction of O-sulfonylated hydroxamic acids with nucleophiles. A new method for the synthesis of .alpha.-substituted amides
  作者：Robert V. Hoffman、Naresh K. Nayyar、Wenting Chen

  DOI：10.1021/jo00047a024

  日期：1992.10

  Treatment of a series of hydroxamic acids 2 with mesyl chloride in the presence of 2 equiv of triethylamine at 0-degrees-C gives 2-chloroamides 3 in good yields. Use of a single equivalent of triethylamine gives the (N-mesyl-oxy)amides 1, which are versatile synthetic intermediates as they can be readily converted to 2-bromoamides 4 with lithium bromide and triethylamine and to 2-hydroxyamides 5 with triethylamine in aqueous acetonitrile.