N-(1-(naphthalen-1-yl)-3-oxo-3-phenylpropyl)acetamide | 1240398-50-8

• 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-(1-(naphthalen-1-yl)-3-oxo-3-phenylpropyl)acetamide
• 英文别名: N-{1-(naphthalen-1-yl)-3-oxo-3-phenylpropyl}acetamide；N-(1-(naphth-1-yl)-3-oxo-3-phenylpropyl)acetamide；N-(1-naphthalen-1-yl-3-oxo-3-phenylpropyl)acetamide
• CAS: 1240398-50-8
• 化学式: C₂₁H₁₉NO₂
• 分子量: 317.387
• InChiKey: DZORKIKULWZFLK-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

• 作为产物：
  描述：

  1-萘甲醛 、 苯乙酮 、 乙腈 在 silver trifluoromethanesulfonate 、 乙酰氯 作用下， 反应 12.0h， 以95%的产率得到N-(1-(naphthalen-1-yl)-3-oxo-3-phenylpropyl)acetamide
  参考文献：
  名称：

  Efficient Synthesis of β-Acetamido Ketones by Silver(I) Triflate-Catalyzed Multicomponent Reactions

  摘要：

  在 AgOTf 催化下，取代的苯乙酮与芳香醛和酰氯在乙腈中发生多组分反应，实现了 ${\beta}$-acetamido ketones 的高效一锅合成，产率很高。这些方法具有操作简便、反应条件温和以及使用高效无毒催化剂等显著优点。

  DOI：

  10.5012/bkcs.2012.33.11.3559

文献信息

• 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.
• KAl (SO₄)₂.12H₂O or KHSO₄: Efficient and Inexpensive Catalysts for the One-Pot Synthesis of β-Acetamido Ketones by Dakin–West Reaction
  作者：Majid M. Heravi、Masoumeh Zakeri、Narges Mohammadi、Hoda Haghi

  DOI：10.1080/15533174.2011.609514

  日期：2012.2.1

  Aromatic aldehydes were reacted in a vessel with enolizable ketones, acetonitrile, and acetyl chloride at ambient temperature in the presence of KAl(SO4)(2)center dot 12H(2)O to furnish the corresponding beta-acetamido ketones in excellent yields. KHSO4 has also been used as another catalyst for this reaction at room temperature. Key features of this methodology are operational simplicity, mild reaction conditions, and excellent yields.
• Efficient Synthesis of β-Acetamido Ketones by Silver(I) Triflate-Catalyzed Multicomponent Reactions
  作者：Rameshwar Prasad Pandit、Yong Rok Lee

  DOI：10.5012/bkcs.2012.33.11.3559

  日期：2012.11.20

  An efficient one-pot synthesis of $\beta}$-acetamido ketones was accomplished by AgOTf-catalyzed multicomponent reactions of substituted acetophenones with aromatic aldehydes and acid chloride in acetonitrile in high yields. The methods offer several significant advantages of easy handling, mild reaction conditions, and use of effective and non-toxic catalyst.

  在 AgOTf 催化下，取代的苯乙酮与芳香醛和酰氯在乙腈中发生多组分反应，实现了 $\beta}$-acetamido ketones 的高效一锅合成，产率很高。这些方法具有操作简便、反应条件温和以及使用高效无毒催化剂等显著优点。