(E)-N-methyl-N-(3-methyl-4-phenylbut-3-en-1-yn-1-yl)methanesulfonamide | 1384432-41-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-N-methyl-N-(3-methyl-4-phenylbut-3-en-1-yn-1-yl)methanesulfonamide
• 英文别名: (E)-N-methyl-N-(3-methyl-4-phenylbut-3-en-1-ynyl)methanesulfonamide；N-methyl-N-[(E)-3-methyl-4-phenylbut-3-en-1-ynyl]methanesulfonamide
• CAS: 1384432-41-0
• 化学式: C₁₃H₁₅NO₂S
• 分子量: 249.334
• InChiKey: IUURCKVODQYIRZ-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-N-methyl-N-(3-methyl-4-phenylbut-3-en-1-yn-1-yl)methanesulfonamide 在 三氟甲磺酸三甲基硅酯 、 氢溴酸 、 zinc trifluoromethanesulfonate 、 二异丙胺 、 zinc dibromide 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 5.75h， 生成 N-(4-bromo-5-phenylfuran-2-yl)-N,4-dimethylbenzenesulfonamide
  参考文献：
  名称：

  Zn(II)- or Ag(I)-Catalyzed 1,4-Metathesis Reactions between 3-En-1-ynamides and Nitrosoarenes

  摘要：

  Catalyst-dependent metathesis reactions between 3-en-1-ynamides and nitrosoarenes are described. Particularly notable are the unprecedented 1,4-metathesis reactions catalyzed by Ag(I) or Zn(II) to give 2-propynimidamides and benzaldehyde derivatives. With 3-en-1-ynamides bearing a cycloalkenyl group, 1,4-oxoimination products were produced efficiently. We have developed metathesis/alkynation cascades for unsubstituted 2-propynimidamides and benzaldehyde species generated in situ, to manifest 1,4-hydroxyimination reactions of 3-en-1-ynes. Both 1,4-oxoiminations and 1,4-hydroxyiminations increase the molecular complexity of products.

  DOI：

  10.1021/ja412634w
• 作为产物：
  描述：

  (E)-(2-methylbut-1-en-3-yn-1-yl)benzene 在 N-溴代丁二酰亚胺(NBS) 、 1,10-菲罗啉 、 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 silver nitrate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 3.0h， 生成 (E)-N-methyl-N-(3-methyl-4-phenylbut-3-en-1-yn-1-yl)methanesulfonamide
  参考文献：
  名称：

  Gold-catalyzed synthesis of substituted 2-aminofurans via formal [4+1]-cycloadditions on 3-en-1-ynamides

  摘要：

  报告了金催化 3-en-1-ynamides 1 与 8-甲基氧化喹啉之间的正式 [4+1]-cycloadditions 反应。该反应的成功依赖于金稳定烯丙基阳离子上的假想氧杂纳扎洛夫环化反应。此外，还报告了 3-烯-1-炔酰胺的一种新的 1,2-二官能化的初步结果。

  DOI：

  10.1039/c2cc33030j

文献信息

• Regiocontrolled Gold-Catalyzed [2+2+2] Cycloadditions of Ynamides with Two Discrete Nitriles to Construct 4-Aminopyrimidine Cores
  作者：Somnath Narayan Karad、Rai-Shung Liu

  DOI：10.1002/anie.201405312

  日期：2014.8.18

  Reported herein is the novel gold‐catalyzed intermolecular [2+2+2] cycloaddition of ynamides with two discrete nitriles to form monomeric 4‐aminopyrimidines, which are pharmaceutically important structural motifs. The utility of this new cycloaddition is demonstrated by the excellent regioselectivity obtained using a variety of ynamides and nitriles.

  本文报道的是新型的金催化的酰胺类分子间[2 + 2 + 2]分子间环加成反应，形成两个离散的腈基，形成单体的4-氨基嘧啶，这是药学上重要的结构基序。通过使用多种酰胺和腈获得的优异的区域选择性证明了这种新的环加成反应的实用性。
• Gold- and Silver-Catalyzed [4+2] Cycloadditions of Ynamides with Oxetanes and Azetidines
  作者：Samir Kundlik Pawar、Dhananjayan Vasu、Rai-Shung Liu

  DOI：10.1002/adsc.201400024

  日期：2014.8.11

  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
• Zinc-Catalyzed Stereo- and Regioselective 1,4-Hydrative Fluorination of 3-En-1-ynamides with Selectfluor
  作者：Appaso Mahadev Jadhav、Deepak B. Huple、Rahulkumar Rajmani Singh、Rai Shung Liu

  DOI：10.1002/adsc.201501021

  日期：2016.3.31

  AbstractZinc‐catalyzed 1,4‐oxofluorinations of 3‐en‐1‐ynamides with Selectfluor in acetonitrile/water proceeded with high regio‐ and stereoselectivity, giving E‐configured γ‐fluoro‐α,β‐unsaturated amides efficiently. Our control experiments indicate that kinetically unstable C‐bound zinc dienolates are chemically reactive to undergo SE2′‐electrophilic fluorinations whereas the detectable O‐bound dienolates preferably undergo protodemetalation reactions instead.magnified image