N-allyl-N-(4-chlorophenyl)hydroxylamine | 117531-29-0

• 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-allyl-N-(4-chlorophenyl)hydroxylamine
• 英文别名: N-(4-chlorophenyl)-N-prop-2-enylhydroxylamine
• CAS: 117531-29-0
• 化学式: C₉H₁₀ClNO
• 分子量: 183.637
• InChiKey: HPMNOKYHLGTNPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-allyl-N-(4-chlorophenyl)hydroxylamine 、 三氯乙酰氯 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 8.0h， 以86%的产率得到3-allyl-6-chlorobenzoxazolone
  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：

  乙酸烯丙酯 、 4-氯苯基羟胺 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到N-allyl-N-(4-chlorophenyl)hydroxylamine
  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

• Unexpected reactivity of allyl magnesium chloride with nitroarenes. A general method of synthesis of N-allyl-N-arylhydroxylamines and N-allylanilines
  作者：Giuseppe Bartoli、Enrico Marcantoni、Marcella Bosco、Renato Dalpozzo

  DOI：10.1016/s0040-4039(00)86724-6

  日期：——
• BARBON, LUCIANO;BARTOLI, GIUSEPPE;MARCANTONI, ENRICO;PETRINI, MARINO;DALP+, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 2133-2138
  作者：BARBON, LUCIANO、BARTOLI, GIUSEPPE、MARCANTONI, ENRICO、PETRINI, MARINO、DALP+

  DOI：——

  日期：——
• BARTOLI, GIUSEPPE;MARCANTONI, ENRICO;BOSCO, MARCELLA;DALPOZZO, RENATO, TETRAHEDRON LETT., 29,(1988) N 18, 2251-2254
  作者：BARTOLI, GIUSEPPE、MARCANTONI, ENRICO、BOSCO, MARCELLA、DALPOZZO, RENATO

  DOI：——

  日期：——