N-(3-(naphthalen-2-yl)-3-oxo-1-phenylpropyl)acetamide | 1181766-63-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: N-(3-(naphthalen-2-yl)-3-oxo-1-phenylpropyl)acetamide
• 英文别名: N-(3-(naphth-2-yl)-3-oxo-1-phenylpropyl)acetamide；N-(3-naphthalen-2-yl-3-oxo-1-phenylpropyl)acetamide
• CAS: 1181766-63-1
• 化学式: C₂₁H₁₉NO₂
• 分子量: 317.387
• InChiKey: CXQVHYYQDNFOOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-(naphthalen-2-yl)-3-oxo-1-phenylpropyl)acetamide 在 potassium iodide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.0h， 以71%的产率得到rac-((4R,5S)-2-methyl-4-phenyl-4,5-dihydrooxazol-5-yl)(naphthalen-2-yl)methanone
  参考文献：
  名称：

  Electrosynthesis of Trisubstituted 2-Oxazolines via Dehydrogenative Cyclization of β-Amino Arylketones

  摘要：

  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.

  DOI：

  10.1021/acs.orglett.8b00165
• 作为产物：
  描述：

  苯甲醛 、 乙腈 、 2-萘乙酮 在 iron(III) chloride 、 乙酰氯 作用下， 反应 24.0h， 以68%的产率得到N-(3-(naphthalen-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。
• Tetrachlorosilane-Zinc Chloride as a New Potent Binary Reagent for One-Pot, Three-Component Synthesis of Mannich-Type Products
  作者：Doria S. Badawy、Ebrahim Abdel-Galil、Ezzat M. Kandeel、Wahid M. Basyouni、Tamer K. Khatab

  DOI：10.1080/10426500802589907

  日期：2009.10.30

  A combination of tetrachlorosilane and zinc chloride in dichloromethane as an efficient and ambient binary reagent to promote a one-pot amidoalkylation reaction of enolizable ketones, aromatic aldehydes with acetonitriles, or benzonitrile have been developed. The newly synthesized beta-acetamidoketones 3 and beta-benzamidoketones 5 were obtained in good yields.
• 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.
• 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.