ethyl 2-phenyl-1-pyrroline-5-carboxylate 1-oxide | 212265-33-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-phenyl-1-pyrroline-5-carboxylate 1-oxide
• 英文别名: ethyl 1-oxido-5-phenyl-3,4-dihydro-2H-pyrrol-1-ium-2-carboxylate
• CAS: 212265-33-3
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: FORVCMSCFFPJFS-UHFFFAOYSA-N

物化性质

• 沸点：
  373.0±52.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-phenyl-1-pyrroline-5-carboxylate 1-oxide 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 168.0h， 生成 ethyl 6-phenyl-8-oxa-7-azatricyclo[4.2.1.0^3,7]nonane-3-carboxylate
  参考文献：
  名称：

  Synthesis and Reactivity of 1-Pyrroline-5-carboxylate Ester 1-Oxides

  摘要：

  Some C5 mono- and diester-substituted 1-pyrroline-1-oxides have been prepared via reductive cyclisation of the corresponding gamma-nitro carbonyl compounds. Ethyl 2-phenyl-1-pyrroline-1-oxide-5-carboxylate 5c was regioselectively alkylated at C5. Acylation of this molecule occurs exclusively on the nitrone oxygen and leads to C3 substituted pyrrolines as the result of a hetero-Cope rearrangement. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00094-6
• 作为产物：
  描述：

  吖啶橙 在 氯化铵 、 锌 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 生成 ethyl 2-phenyl-1-pyrroline-5-carboxylate 1-oxide
  参考文献：
  名称：

  Synthesis and Reactivity of 1-Pyrroline-5-carboxylate Ester 1-Oxides

  摘要：

  Some C5 mono- and diester-substituted 1-pyrroline-1-oxides have been prepared via reductive cyclisation of the corresponding gamma-nitro carbonyl compounds. Ethyl 2-phenyl-1-pyrroline-1-oxide-5-carboxylate 5c was regioselectively alkylated at C5. Acylation of this molecule occurs exclusively on the nitrone oxygen and leads to C3 substituted pyrrolines as the result of a hetero-Cope rearrangement. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00094-6

文献信息

• Synthesis and Radical Reactions of Isomeric Alkenyl Oxaziridines
  作者：David Black、Gavin Edwards、Sean Laaman

  DOI：10.1055/s-2006-942380

  日期：2006.6

  stereoselectivity are discussed. Reaction of the oxaziridines with iron(II) sulfate, tributyltin hydride, or copper(I)triphenylphosphine chloride tetramer gave products arising from deoxygenation in many cases; however the trans-isomers also gave products derived from cyclisation of the intermediate aminyl radicals onto the pendant alkenyl chains.

  通过前体硝酮的光异构化或通过类似吡咯啉的过酸氧化制备几种烯基恶氮丙啶。在每种情况下，恶氮丙啶都是作为非对映异构体的可分离混合物产生的，并讨论了观察到的立体选择性的原因。在许多情况下，氧氮丙啶与硫酸铁 (II)、氢化三丁基锡或三苯基膦氯化铜 (I) 四聚体反应会产生脱氧产物；然而，反式异构体也产生了衍生自中间胺基环化到侧链烯基链上的产物。
• Synthesis and Reactivity of 1-Pyrroline-5-carboxylate Ester 1-Oxides
  作者：David StC. Black、Gavin L. Edwards、Richard H. Evans、Paul A. Keller、Sean M. Laaman

  DOI：10.1016/s0040-4020(00)00094-6

  日期：2000.3

  Some C5 mono- and diester-substituted 1-pyrroline-1-oxides have been prepared via reductive cyclisation of the corresponding gamma-nitro carbonyl compounds. Ethyl 2-phenyl-1-pyrroline-1-oxide-5-carboxylate 5c was regioselectively alkylated at C5. Acylation of this molecule occurs exclusively on the nitrone oxygen and leads to C3 substituted pyrrolines as the result of a hetero-Cope rearrangement. (C) 2000 Elsevier Science Ltd. All rights reserved.