4-methyl-N-(5-oxo-cyclohept-1-enylmethyl)benzenesulfonamide

• 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: 4-methyl-N-(5-oxo-cyclohept-1-enylmethyl)benzenesulfonamide
• 英文别名: 4-methyl-N-[(5-oxocyclohepten-1-yl)methyl]benzenesulfonamide
• 化学式: C₁₅H₁₉NO₃S
• 分子量: 293.387
• InChiKey: WOXQHDFLTKKTOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲基-N-(丙-2-炔-1-基)苯-1-磺酰胺 、 1-乙烯基-1-(2-甲氧基乙氧基)环丙烷 在 di(rhodium)tetracarbonyl dichloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.25h， 以87%的产率得到4-methyl-N-(5-oxo-cyclohept-1-enylmethyl)benzenesulfonamide
  参考文献：
  名称：

  A New and Practical Five-Carbon Component for Metal-Catalyzed [5 + 2] Cycloadditions:  Preparative Scale Syntheses of Substituted Cycloheptenones

  摘要：

  Described herein is an efficient preparative scale synthesis of 1-(2-methyoxyethoxy)-1-vinylcyclopropane and the investigation of the utility of this reagent as a new five-carbon component in metal-catalyzed [5 + 2] cycloadditions. A new cycloaddition procedure is also described that proceeds up to 12-fold faster and with 10-fold less catalyst than previously described, providing cycloheptenones in many cases in minutes and in isolated yields of 75-97%. The procedure is readily conducted on a small or large scale (up to 100 mmol thus far).

  DOI：

  10.1021/ol0058691

文献信息

• Highly Efficient, Facile, Room Temperature Intermolecular [5 + 2] Cycloadditions Catalyzed by Cationic Rhodium(I): One Step to Cycloheptenes and Their Libraries
  作者：Paul A. Wender、Lauren E. Sirois、René T. Stemmler、Travis J. Williams

  DOI：10.1021/ol100337m

  日期：2010.4.2

  A cationic rhodium(I) complex-[(C(10)H(8))Rh(cod)](+) SbF(6)(-)-Catalyzes the remarkably efficient intermolecular [5 + 2] cycloaddition of vinylcyclopropanes (VCPs) and various alkynes, providing cycloheptene cycloadducts in excellent yields in minutes at room temperature. The efficacy and selectivity of this catalyst are also shown in a novel diversification strategy, affording a cycloadduct library in one step from nine commercially available components.
• A New and Practical Five-Carbon Component for Metal-Catalyzed [5 + 2] Cycloadditions:  Preparative Scale Syntheses of Substituted Cycloheptenones
  作者：Paul A. Wender、Alaric J. Dyckman、Craig O. Husfeld、Marc J. C. Scanio

  DOI：10.1021/ol0058691

  日期：2000.6.1

  Described herein is an efficient preparative scale synthesis of 1-(2-methyoxyethoxy)-1-vinylcyclopropane and the investigation of the utility of this reagent as a new five-carbon component in metal-catalyzed [5 + 2] cycloadditions. A new cycloaddition procedure is also described that proceeds up to 12-fold faster and with 10-fold less catalyst than previously described, providing cycloheptenones in many cases in minutes and in isolated yields of 75-97%. The procedure is readily conducted on a small or large scale (up to 100 mmol thus far).
• THE PREPARATION OF CYCLOHEPT-4-ENONES BY RHODIUM-CATALYZED INTERMOLECULAR [5+2] CYCLOADDITION
  作者：Wender, Paul A.、Lesser, Adam B.、Sirois, Lauren E.

  DOI：10.15227/orgsyn.088.0109

  日期：——