3-(2-ethoxycarbonylethyl)-6-chlorobenzoxazolone | 19178-61-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 3-(2-ethoxycarbonylethyl)-6-chlorobenzoxazolone
• 英文别名: 3-(6-chloro-2-oxo-benzooxazol-3-yl)-propionic acid ethyl ester；Ethyl 3-(6-chloro-2-oxo-1,3-benzoxazol-3-yl)propanoate；ethyl 3-(6-chloro-2-oxo-1,3-benzoxazol-3-yl)propanoate
• CAS: 19178-61-1
• 化学式: C₁₂H₁₂ClNO₄
• 分子量: 269.685
• InChiKey: PQWDZSQLFKDMKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-ethoxycarbonylethyl)-6-chlorobenzoxazolone 在 氨 作用下， 以 乙醇 为溶剂， 生成 3-(6-chloro-2-oxo-benzooxazol-3-yl)-propionamide
  参考文献：
  名称：

  Lespagnol,A. et al., Chimica Therapeutica, 1967, vol. 2, p. 343 - 346

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(2-氧代-2,3-二氢-1,3-苯并噁唑)丙腈 在 盐酸 、 硫酸 、 potassium perchlorate 作用下， 生成 3-(2-ethoxycarbonylethyl)-6-chlorobenzoxazolone
  参考文献：
  名称：

  Lespagnol,A. et al., Chimica Therapeutica, 1967, vol. 2, p. 343 - 346

  摘要：

  DOI：

文献信息

• Synthesis of 3-Alkylbenzoxazolones from <i>N</i>-Alkyl-<i>N</i>-arylhydroxylamines by Contiguous <i>O</i>-Trichloroacetylation, Trichloroacetoxy <i>ortho</i>-Shift, and Cyclization Sequence
  作者：Ram N. Ram、Vineet Kumar Soni

  DOI：10.1021/jo401985h

  日期：2013.12.6

  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.
• Lespagnol,Ch. et al., Chimica Therapeutica, 1970, vol. 5, p. 201 - 204
  作者：Lespagnol,Ch. et al.

  DOI：——

  日期：——
• Lespagnol,A. et al., Chimica Therapeutica, 1967, vol. 2, p. 343 - 346
  作者：Lespagnol,A. et al.

  DOI：——

  日期：——