4-(hydroxyamino)phenyl acetate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-(hydroxyamino)phenyl acetate
• 英文别名: -hydroxylamin；[4-(Hydroxyamino)phenyl] acetate
• 化学式: C₈H₉NO₃
• 分子量: 167.164
• InChiKey: SYPAAZQSEVVXNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(hydroxyamino)phenyl acetate 在 sodium tetrahydroborate 、 氯化铵 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 11.0h， 生成 3-benzyl-6-acetoxybenzoxazolone
  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：

  4-硝基苯基乙酸酯 在 一水合肼 作用下， 以 氯仿 为溶剂， 反应 1.25h， 生成 4-氨基苯乙酸 、 4-(hydroxyamino)phenyl acetate
  参考文献：
  名称：

  通过使用可溶性纳米颗粒催化剂部分还原硝基芳烃来合成N-芳基和N-杂芳基羟胺

  摘要：

  聚苯乙烯负载的钌纳米颗粒能够以高收率和选择性将肼介导的硝基芳烃选择性还原为羟胺产物。以高收率获得羟胺产物的关键是使用能够溶解聚苯乙烯负载的纳米颗粒催化剂的有机溶剂。N-芳基和N-杂芳基羟胺是在异常温和的条件下，在各种容易还原的官能团存在下生成的。

  DOI：

  10.1016/j.tetlet.2016.11.105

文献信息

• US3982922A
  申请人：——

  公开号：US3982922A

  公开（公告）日：1976-09-28