N-methyl-N-(naphthalen-2-yl)methanesulfonamide | 1357012-30-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-methyl-N-(naphthalen-2-yl)methanesulfonamide
• 英文别名: N-methyl-N-naphthalen-2-ylmethanesulfonamide
• CAS: 1357012-30-6
• 化学式: C₁₂H₁₃NO₂S
• 分子量: 235.307
• InChiKey: KPRPMDWTSCMTTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-methyl-N-[(E)-1-phenylbut-1-en-3-yn-2-yl]methanesulfonamide 在 platinum(II) chloride 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以70%的产率得到N-methyl-N-(naphthalen-2-yl)methanesulfonamide
  参考文献：
  名称：

  钯催化末端炔烃交叉加成至芳基酰胺：一种不寻常的反式-氢化炔基化反应

  摘要：

  AbstractA palladium‐catalyzed trans‐hydroalkynylation of N‐sulfonyl ynamides has been achieved for the first time, providing α‐alkynylation adducts in high yields with excellent regio‐ and stereoselectivity. The resulting enyne products can serve as the useful precursors for the elaboration of naphthalene derivatives via a platinum‐catalyzed cycloisomerization reaction.magnified image

  DOI：

  10.1002/adsc.201400572

文献信息

• Gold-Catalyzed Intermolecular [4+2] and [2+2+2] Cycloadditions of Ynamides with Alkenes
  作者：Ramesh B. Dateer、Balagopal S. Shaibu、Rai-Shung Liu

  DOI：10.1002/anie.201105921

  日期：2012.1.2

  As good as gold: Gold‐catalyzed intermolecular [4+2] cycloadditions of 2‐arylynamides with alkenes and gold‐catalyzed [2+2+2] cycloadditions of terminal ynamides with enol ethers have been developed (see scheme). The [4+2] cycloaddition is compatible with a range of alkenes and arylynamides and the [2+2+2] cycloaddition can also accommodate a variety of different arylynamide and enol ether substrates

  与金一样好：已开发了金催化的2-芳基酰胺与烯烃的分子间[4 + 2]环加成反应，以及金催化的端烯酰胺与烯醇醚的[2 + 2 + 2]环加成反应（参见方案）。[4 + 2]环加成与一系列烯烃和芳基酰胺相容，[2 + 2 + 2]环加成还可容纳多种不同的芳基酰胺和烯醇醚底物。
• Palladium-Catalyzed Cross Addition of Terminal Alkynes to Aryl Ynamides: An Unusual<i>trans</i>-Hydroalkynylation Reaction
  作者：Ge Liu、Wei Kong、Jianwei Che、Gangguo Zhu

  DOI：10.1002/adsc.201400572

  日期：2014.11.3

  AbstractA palladium‐catalyzed trans‐hydroalkynylation of N‐sulfonyl ynamides has been achieved for the first time, providing α‐alkynylation adducts in high yields with excellent regio‐ and stereoselectivity. The resulting enyne products can serve as the useful precursors for the elaboration of naphthalene derivatives via a platinum‐catalyzed cycloisomerization reaction.magnified image