N-(but-2-yn-1-yl)-4-methyl-N-(2-oxo-2-phenylethyl)benzenesulfonamide | 1427797-93-0

• 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: N-(but-2-yn-1-yl)-4-methyl-N-(2-oxo-2-phenylethyl)benzenesulfonamide
• 英文别名: N-but-2-ynyl-4-methyl-N-phenacylbenzenesulfonamide
• CAS: 1427797-93-0
• 化学式: C₁₉H₁₉NO₃S
• 分子量: 341.431
• InChiKey: PCDUMNGRVNRJFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(but-2-yn-1-yl)-4-methyl-N-(2-oxo-2-phenylethyl)benzenesulfonamide 在 silver trifluoromethanesulfonate 作用下， 以 硝基甲烷 为溶剂， 反应 16.0h， 以71%的产率得到(3-methyl-1-tosyl-2,5-dihydro-1H-pyrrol-2-yl)(phenyl)methanone
  参考文献：
  名称：

  Silver(I)‐Catalyzed Conia‐Ene Reaction: Synthesis of 3‐Pyrrolines via a 5‐ endo ‐ dig Cyclization

  摘要：

  AbstractA novel method has been developed for the synthesis of 3‐pyrrolines from β‐ketopropargylamines via a 5‐endo‐dig carbocyclization. This transformation involves a silver‐catalyzed Conia‐ene type reaction tolerating broad substrate scope with good to excellent yields. Furthermore, this methodology has been extended for the construction of 2‐substituted pyrroles under base‐mediated conditions.magnified image

  DOI：

  10.1002/adsc.201300844
• 作为产物：
  描述：

  苯乙酮 在 四丁基碘化铵 、 potassium carbonate 、 copper(ll) bromide 作用下， 以 氯仿 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 N-(but-2-yn-1-yl)-4-methyl-N-(2-oxo-2-phenylethyl)benzenesulfonamide
  参考文献：
  名称：

  Silver(I)‐Catalyzed Conia‐Ene Reaction: Synthesis of 3‐Pyrrolines via a 5‐ endo ‐ dig Cyclization

  摘要：

  AbstractA novel method has been developed for the synthesis of 3‐pyrrolines from β‐ketopropargylamines via a 5‐endo‐dig carbocyclization. This transformation involves a silver‐catalyzed Conia‐ene type reaction tolerating broad substrate scope with good to excellent yields. Furthermore, this methodology has been extended for the construction of 2‐substituted pyrroles under base‐mediated conditions.magnified image

  DOI：

  10.1002/adsc.201300844

文献信息

• Cationic Pd(II)-Catalyzed Reductive Cyclization of Alkyne-Tethered Ketones or Aldehydes Using Ethanol as Hydrogen Source
  作者：Kun Shen、Xiuling Han、Xiyan Lu

  DOI：10.1021/ol400531a

  日期：2013.4.5

  A cationic Pd(II)-catalyzed reductive cyclization of alkyne-tethered ketones or aldehydes using ethanol as hydrogen source under mild conditions was developed. The reaction is an environmentally benign synthetic method and proceeds efficiently to give useful N-heterocycles or carbocycles bearing an exocyclic double bond and a hydroxyl group in high yield.

  在温和条件下，使用乙醇作为氢源，开发了阳离子Pd（II）催化炔烃系酮或醛的还原环化反应。该反应是对环境无害的合成方法，并有效地进行，以高收率得到有用的带有杂环外双键和羟基的N-杂环或碳环。
• Rhodium-Catalyzed Asymmetric Tandem Cyclization for Efficient and Rapid Access to Underexplored Heterocyclic Tertiary Allylic Alcohols Containing a Tetrasubstituted Olefin
  作者：Yi Li、Ming-Hua Xu

  DOI：10.1021/ol500993h

  日期：2014.5.16

  Rh-catalyzed asymmetric tandem cyclization of nitrogen- or oxygen-bridged 5-alkynones with arylboronic acids was achieved. The simple catalytic system involving a rhodium(I) complex with readily available chiral BINAP ligand promotes the reaction to proceed in a highly stereocontrolled manner. This protocol provides a very reliable and practical access to a variety of chiral heterocyclic tertiary allylic

  实现了第一个Rh催化的氮或氧桥接的5-炔基与芳基硼酸的不对称串联环化反应。包含铑（I）配合物和易于获得的手性BINAP配体的简单催化体系可促进反应以高度立体可控的方式进行。该方案以高收率和高达99％ee的高对映选择性提供了一种非常可靠和实用的途径，可用于获得具有四取代碳立体中心和全碳四取代烯烃官能度的各种手性杂环叔烯丙基醇。
• Silver(I)‐Catalyzed Conia‐Ene Reaction: Synthesis of 3‐Pyrrolines <i>via</i> a 5‐ <i>endo</i> ‐ <i>dig</i> Cyclization
  作者：Siva Senthil Kumar Boominathan、Wan‐Ping Hu、Gopal Chandru Senadi、Jeh‐Jeng Wang

  DOI：10.1002/adsc.201300844

  日期：2013.12.16

  AbstractA novel method has been developed for the synthesis of 3‐pyrrolines from β‐ketopropargylamines via a 5‐endo‐dig carbocyclization. This transformation involves a silver‐catalyzed Conia‐ene type reaction tolerating broad substrate scope with good to excellent yields. Furthermore, this methodology has been extended for the construction of 2‐substituted pyrroles under base‐mediated conditions.magnified image