2-(5-Acetyl-3-nitro-2-thienyloxy)propionsaeureethylester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-(5-Acetyl-3-nitro-2-thienyloxy)propionsaeureethylester
• 英文别名: ethyl 2-(5-acetyl-3-nitrothiophen-2-yl)oxypropanoate
• 化学式: C₁₁H₁₃NO₆S
• 分子量: 287.293
• InChiKey: CPDNJPQHMMUIGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  95.74
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-(5-Acetyl-3-nitro-2-thienyloxy)propionsaeureethylester 在 铁粉 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 以75%的产率得到6-Acetyl-3-methyl-1H-thieno<2,3-b><1,4>oxazin-2(3H)-on
  参考文献：
  名称：

  Studien zur Chemie von thienoanellierten O,N-und S,N-haltigen Heterocyclen, 5. Mitt.: Ein Zugang zum Thieno[2,3-b][1,4]oxazin-Ringsystem

  摘要：

  The reactivity of 5-acetyl-2-chloro-3-nitrothiophene with alpha-hydroxyesters is described. The influence of the solvent (DMF, tetrahydrofurane, toluene) and of the used base is discussed. These reactions provide an access to substituted thiophene derivatives, which were cyclized after reduction by iron powder/glacial acetic acid to give thieno [2,3-b][1,4]oxazine derivatives.

  DOI：

  10.1007/bf00812707
• 作为产物：
  描述：

  乳酸乙酯 、 1-(5-氯-4-硝基-2-噻吩)-1-乙酮 在 sodium hydride 作用下， 生成 2-(5-Acetyl-3-nitro-2-thienyloxy)propionsaeureethylester
  参考文献：
  名称：

  Studien zur Chemie von thienoanellierten O,N-und S,N-haltigen Heterocyclen, 5. Mitt.: Ein Zugang zum Thieno[2,3-b][1,4]oxazin-Ringsystem

  摘要：

  The reactivity of 5-acetyl-2-chloro-3-nitrothiophene with alpha-hydroxyesters is described. The influence of the solvent (DMF, tetrahydrofurane, toluene) and of the used base is discussed. These reactions provide an access to substituted thiophene derivatives, which were cyclized after reduction by iron powder/glacial acetic acid to give thieno [2,3-b][1,4]oxazine derivatives.

  DOI：

  10.1007/bf00812707

文献信息

• Puschmann I., Erker T., Monatsh. Chem, 125 (1994) N 8-9, S 927-932
  作者：Puschmann I., Erker T.

  DOI：——

  日期：——
• Studien zur Chemie von thienoanellierten O,N-und S,N-haltigen Heterocyclen, 5. Mitt.: Ein Zugang zum Thieno[2,3-b][1,4]oxazin-Ringsystem
  作者：I. Puschmann、T. Erker

  DOI：10.1007/bf00812707

  日期：——

  The reactivity of 5-acetyl-2-chloro-3-nitrothiophene with alpha-hydroxyesters is described. The influence of the solvent (DMF, tetrahydrofurane, toluene) and of the used base is discussed. These reactions provide an access to substituted thiophene derivatives, which were cyclized after reduction by iron powder/glacial acetic acid to give thieno [2,3-b][1,4]oxazine derivatives.