ethyl 2-oxo-3(2H)-benzoxazolepropionate | 19178-54-2

• 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: ethyl 2-oxo-3(2H)-benzoxazolepropionate
• 英文别名: 3-(2-ethoxycarbonylethyl)benzoxazolone；3-(2-oxo-benzooxazol-3-yl)-propionic acid ethyl ester；Ethyl 3-(2-oxo-1,3-benzoxazol-3-yl)propanoate
• CAS: 19178-54-2
• 化学式: C₁₂H₁₃NO₄
• mdl: MFCD02085189
• 分子量: 235.24
• InChiKey: IPJARCFYDHGAEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 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：

  ethyl 2-oxo-3(2H)-benzoxazolepropionate 在 一水合肼 作用下， 生成 3-(2-oxo-benzooxazol-3-yl)-propionic acid hydrazide
  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：

  2-苯并唑啉酮 在 硫酸 、 苄基三甲基氢氧化铵 作用下， 生成 ethyl 2-oxo-3(2H)-benzoxazolepropionate
  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 1-(2-hydroxyphenyl)-2,4-imidazolidinedione derivatives through cyclic transformations of ethyl 2-oxo-3(2<i>H</i>)-benzoxazoleacetate derivatives
  作者：René Milcent、Anna Akhnazarian、Nathalie Lensen

  DOI：10.1002/jhet.5570330645

  日期：1996.11

  A series of ethyl 2-oxo-3(2H)-benzoxazoleacetate derivatives 2 have been synthesized. By reaction with ammonia, primary amines or hydrazine, these compounds 2 were transformed into 1-(2-hydroxyphenyl)-2,4-imidazolidinedione derivatives 4, 5 and 6, respectively. Some of these new hydantoins 4, treated with phosphorus oxychloride, gave 3H-2-oxoimidazo[2,1-b]benzoxazole derivatives 9. Ethyl 2-oxo-3(2H

  合成了一系列2-氧代-3（2 H）-苯并恶唑乙酸乙酯衍生物2。通过与氨，伯胺或肼反应，将这些化合物2分别转化为1-（2-羟苯基）-2，4-咪唑烷二酮衍生物4、5和6。这些新的乙内酰脲4，用三氯氧磷处理后，得到3 H -2-氧代咪唑并[2,1- b ]苯并恶唑衍生物9。通过丙烯酸乙酯与2-苯并恶唑酮（1a）的Michaël反应制备2-氧代-3（2 H）-苯并恶唑丙酸乙酯（10）。带10，在氨或烷基胺的存在下未观察到环状转化。
• 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：——