N-(3-(furan-2-yl)-3-oxo-1-phenylpropyl)acetamide | 1338705-55-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(3-(furan-2-yl)-3-oxo-1-phenylpropyl)acetamide
• 英文别名: N-[3-(furan-2-yl)-3-oxo-1-phenylpropyl]acetamide
• CAS: 1338705-55-7
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: YDHDJBRZQPSOFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  59.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-(furan-2-yl)-3-oxo-1-phenylpropyl)acetamide 在 叔丁基过氧化氢 、 碘 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以70%的产率得到(furan-2-yl)(2-methyl-4-phenyl-4,5-dihydrooxazol-5-yl)methanone
  参考文献：
  名称：

  I₂-Catalyzed C–O Bond Formation and Dehydrogenation: Facile Synthesis of Oxazolines and Oxazoles Controlled by Bases

  摘要：

  A general method for the synthesis of oxazolines and oxazoles was developed through I-2-catalyzed C-O bond formation and dehydrogenation with the same oxidant, TBHP. By simply tuning reaction bases, either oxazolines or oxazoles were selectively produced from beta-acylamino ketones.

  DOI：

  10.1021/acs.orglett.5b01933
• 作为产物：
  描述：

  2-乙酰基呋喃 、 苯甲醛 、 乙腈 在 iron(III) chloride 、 乙酰氯 作用下， 反应 24.0h， 以44%的产率得到N-(3-(furan-2-yl)-3-oxo-1-phenylpropyl)acetamide
  参考文献：
  名称：

  I₂-Catalyzed C–O Bond Formation and Dehydrogenation: Facile Synthesis of Oxazolines and Oxazoles Controlled by Bases

  摘要：

  A general method for the synthesis of oxazolines and oxazoles was developed through I-2-catalyzed C-O bond formation and dehydrogenation with the same oxidant, TBHP. By simply tuning reaction bases, either oxazolines or oxazoles were selectively produced from beta-acylamino ketones.

  DOI：

  10.1021/acs.orglett.5b01933

文献信息

• Iodine-Mediated Oxidative Dehydrogenation of β-Acylamino Ketones for the Highly Stereoselective Synthesis of (Z)-β-Keto­enamides
  作者：Wen-Chao Gao、Yan Qiao、Hong-Hong Chang、Fei Hu、Tao Liu、Xing Li、Wen-Long Wei

  DOI：10.1055/s-0035-1561582

  日期：——

  An iodine-mediated oxidative dehydrogenation of β-acylamino ketones has been developed for the synthesis of β-ketoenamides in moderate to good yields. Only Z-isomers are accessed due to the intramolecular H-bonding interaction in the HI-elimination step.

  已开发出一种碘介导的 β-酰氨基酮氧化脱氢，用于以中等至良好的产率合成 β-酮烯酰胺。由于 HI 消除步骤中的分子内 H 键相互作用，只能访问 Z 异构体。
• Electrosynthesis of Trisubstituted 2-Oxazolines via Dehydrogenative Cyclization of β-Amino Arylketones
  作者：Huiqiao Wang、Jinjin Zhang、Jiajing Tan、Lilan Xin、Yaping Li、Sheng Zhang、Kun Xu

  DOI：10.1021/acs.orglett.8b00165

  日期：2018.5.4

  An electrochemically intramolecular functionalization of C-(sp(3))-H bonds with masked oxygen nucleophiles was developed. With IU as the catalyst and electrolyte, diverse trisubstituted 2-oxazolines were constructed in good to excellent yields. This newly developed electrochemical dehydrogenalive approach features external oxidant-free and additive-free conditions.