N-(3-oxo-1-phenyl-3-(thiophen-2-yl)propyl)acetamide | 1173335-22-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(3-oxo-1-phenyl-3-(thiophen-2-yl)propyl)acetamide
• 英文别名: N-[3-oxo-1-phenyl-3-(thien-2-yl)propyl]acetamide；N-(3-oxo-1-phenyl-3-thiophen-2-ylpropyl)acetamide
• CAS: 1173335-22-2
• 化学式: C₁₅H₁₅NO₂S
• 分子量: 273.356
• InChiKey: NZEPGEZUZFUDCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：
  74.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-oxo-1-phenyl-3-(thiophen-2-yl)propyl)acetamide 在 叔丁基过氧化氢 、 碘 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以74%的产率得到(2-methyl-4-phenyloxazol-5-yl)(thiophen-2-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-乙酰基噻吩 、 苯甲醛 、 乙腈 在 四氯化硅 、 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以80%的产率得到N-(3-oxo-1-phenyl-3-(thiophen-2-yl)propyl)acetamide
  参考文献：
  名称：

  One-Pot Three-Component Synthesis of β -Acylaminoketones Containing a Thiophene Ring by the Use of Tetrachlorosilane-Zinc Chloride as a Binary Reagent Under Ambient Conditions

  摘要：

  A new route for the synthesis of -acylaminoketones containing a thiophene ring through multicomponent condensation reaction of different ketones, different aldehydes, and different nitriles with tetrachlorosilane (TCS) and zinc chloride as the binary reagent is described.

  DOI：

  10.1080/10426500802095921

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。
• One-Pot Three-Component Synthesis of β -Acylaminoketones Containing a Thiophene Ring by the Use of Tetrachlorosilane-Zinc Chloride as a Binary Reagent Under Ambient Conditions
  作者：Doria S. Badawy、Ebrahim Abdel-Galil、E. M. Kandeel、Wahid M. Basyouni、Khairy A. M. El-Bayouki、Tamer K. Khatab

  DOI：10.1080/10426500802095921

  日期：2008.12.23

  A new route for the synthesis of -acylaminoketones containing a thiophene ring through multicomponent condensation reaction of different ketones, different aldehydes, and different nitriles with tetrachlorosilane (TCS) and zinc chloride as the binary reagent is described.
• 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.
• I₂-Catalyzed C–O Bond Formation and Dehydrogenation: Facile Synthesis of Oxazolines and Oxazoles Controlled by Bases
  作者：Wen-Chao Gao、Fei Hu、Yu-Ming Huo、Hong-Hong Chang、Xing Li、Wen-Long Wei

  DOI：10.1021/acs.orglett.5b01933

  日期：2015.8.7

  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.