N-(2-cyanoethyl)-N-phenylhydroxylamine | 41246-17-7

• 分子结构分类: 有机化合物 - 苯类化合物 - N-苯基羟胺
• 英文名称: N-(2-cyanoethyl)-N-phenylhydroxylamine
• 英文别名: β-N-Phenylhydroxylaminopropionitril；3-(N-hydroxyanilino)propanenitrile
• CAS: 41246-17-7
• 化学式: C₉H₁₀N₂O
• 分子量: 162.191
• InChiKey: JWXKSAFLKMNVGM-UHFFFAOYSA-N

物化性质

• 沸点：
  333.4±34.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  47.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-cyanoethyl)-N-phenylhydroxylamine 、 三氯乙酰氯 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 8.0h， 以85%的产率得到3-(2-氧代-2,3-二氢-1,3-苯并噁唑)丙腈
  参考文献：
  名称：

  Synthesis of 3-Alkylbenzoxazolones from N-Alkyl-N-arylhydroxylamines by Contiguous O-Trichloroacetylation, Trichloroacetoxy ortho-Shift, and Cyclization Sequence

  摘要：

  Benzoxazolone pharmacophore is present in clinical pharmaceuticals, drug candidates, and many compounds having a wide spectrum of biological activities. The methods available for the synthesis of benzoxazolones have limited diversity due to problems in accessibility and air-sensitivity of diversely substituted o-aminophenols from which they are generally prepared by cyclocarbonylation with phosgene or its equivalents. The present paper describes a mild method for the synthesis of 3-alkylbenzoxazolones from easily accessible and air-stable nitroarenes. Nitroarenes were converted to N-alkyl-N-arylhydroxylamines in two steps involving partial reduction to arylhydroxylamines followed by selective N-alkylation. Treatment of N-alkyl-N-arylhydroxylamines with trichloroacetyl chloride and triethylamine afforded 3-alkylbenzoxazolones generally in good yields through an uninterrupted three-step sequence involving O-trichloroacetylation, N -> C-ortho trichloroacetoxy shift, and cyclization in a single pot at ambient temperatures. The present method is mild, wide in scope, economical, and regioselective. Many sensitive groups like alkyl and aryl esters, amide, cyano, and the carbon-carbon double bond survive the reaction.

  DOI：

  10.1021/jo401985h
• 作为产物：
  描述：

  苯基羟胺 、 丙烯腈 反应 1.0h， 以100%的产率得到N-(2-cyanoethyl)-N-phenylhydroxylamine
  参考文献：
  名称：

  Synthesis of 3-Alkylbenzoxazolones from N-Alkyl-N-arylhydroxylamines by Contiguous O-Trichloroacetylation, Trichloroacetoxy ortho-Shift, and Cyclization Sequence

  摘要：

  Benzoxazolone pharmacophore is present in clinical pharmaceuticals, drug candidates, and many compounds having a wide spectrum of biological activities. The methods available for the synthesis of benzoxazolones have limited diversity due to problems in accessibility and air-sensitivity of diversely substituted o-aminophenols from which they are generally prepared by cyclocarbonylation with phosgene or its equivalents. The present paper describes a mild method for the synthesis of 3-alkylbenzoxazolones from easily accessible and air-stable nitroarenes. Nitroarenes were converted to N-alkyl-N-arylhydroxylamines in two steps involving partial reduction to arylhydroxylamines followed by selective N-alkylation. Treatment of N-alkyl-N-arylhydroxylamines with trichloroacetyl chloride and triethylamine afforded 3-alkylbenzoxazolones generally in good yields through an uninterrupted three-step sequence involving O-trichloroacetylation, N -> C-ortho trichloroacetoxy shift, and cyclization in a single pot at ambient temperatures. The present method is mild, wide in scope, economical, and regioselective. Many sensitive groups like alkyl and aryl esters, amide, cyano, and the carbon-carbon double bond survive the reaction.

  DOI：

  10.1021/jo401985h

文献信息

• N-(omega)-cyanoalkyl)aminophenols, and their preparation
  申请人：STERLING DRUG INC.

  公开号：EP0262618A2

  公开（公告）日：1988-04-06

  useful as lipoxygenase inhibitors and anti-asthmatic agents, are prepared by acylation of an aminophenol with an ω-haloalkanoyl chloride followed by reduction of the resulting amide then displacement of the halide by cyanide.

  这种可用作脂氧合酶抑制剂和抗哮喘药的化合物是通过氨基苯酚与ω-卤代烷酰氯酰化，然后将生成的酰胺还原，再用氰化物置换卤化物而制备的。
• Jacquier,R. et al., Bulletin de la Societe Chimique de France, 1973, p. 800 - 803
  作者：Jacquier,R. et al.

  DOI：——

  日期：——
• US4083847A
  申请人：——

  公开号：US4083847A

  公开（公告）日：1978-04-11
• US4835180A
  申请人：——

  公开号：US4835180A

  公开（公告）日：1989-05-30