N-(benzofuran-3-ylethynyl)-N-methylmethanesulfonamide | 1357012-10-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: N-(benzofuran-3-ylethynyl)-N-methylmethanesulfonamide
• CAS: 1357012-10-2
• 化学式: C₁₂H₁₁NO₃S
• 分子量: 249.29
• InChiKey: MVFUZAIGPYHNHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  50.52
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-tosyl-2-phenylazetidine 、 N-(benzofuran-3-ylethynyl)-N-methylmethanesulfonamide 在 silver hexafluoroantimonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以47%的产率得到N-(3-(benzofuran-3-yl)-4-phenyl-1-tosyl-1,4,5,6-tetrahydropyridin-2-yl)-N-methylmethanesulfonamide
  参考文献：
  名称：

  金和银催化的[4 + 2]酰胺与氧杂环丁烷和氮杂环丁烷的环加成反应

  摘要：

  AbstractGold‐catalyzed [4+2] cycloadditions between ynamides and oxetanes are described; these reactions involve oxetanes and gold‐π‐ynamides as nucleophiles and electrophiles, respectively. Excellent cycloaddition regioselectivities are achieved over a reasonable range of ynamide and oxetane substrates. For azetidines, their [4+2] cycloadditions with ynamides are implemented more efficiently with silver hexafluoroantimonate, which is also compatible with various ynamides and azetidines. These two cycloadditions provide facile accesses to six‐membered heterocycles such as 6‐amino‐3,4‐dihydro‐2H‐pyrans and 2‐amino‐1,4,5,6‐tetrahydropyridines.magnified image

  DOI：

  10.1002/adsc.201400024

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。
• Retention of Stereochemistry in Gold-Catalyzed Formal [4+3] Cycloaddition of Epoxides with Arenynamides
  作者：Somnath Narayan Karad、Sabyasachi Bhunia、Rai-Shung Liu

  DOI：10.1002/anie.201203723

  日期：2012.8.27

  Golden opportunity: [4+3] Cycloaddition reactions of arenynamides and epoxides are enabled under gold catalysis and have a broad substrate scope (see scheme; Ms=methanesulfonyl). An SN2‐type front‐side attack of phenyl at the oxiranyl ring is expected to cause the retention of stereochemistry.

  千载难逢的机会：[4 + 3]苯甲酰胺和环氧化物的环加成反应在金催化下得以实现，并具有广泛的底物范围（参见方案； Ms =甲磺酰基）。氧杂环戊基环上的一个S N 2型正面进攻性苯环会导致立体化学的保留。