4-methyl-N-(2-methylidenebut-3-enyl)-N-(2-methylprop-2-enyl)benzenesulfonamide | 1449751-48-7

• 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-(2-methylidenebut-3-enyl)-N-(2-methylprop-2-enyl)benzenesulfonamide
• CAS: 1449751-48-7
• 化学式: C₁₆H₂₁NO₂S
• 分子量: 291.414
• InChiKey: MTORJXDWCZGJOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  4-methyl-N-(2-methylallyl)-N-(prop-2-ynyl)benzenesulfonamide 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 40.0 ℃ 、689.49 kPa 条件下， 反应 20.0h， 生成 4-methyl-N-(2-methylidenebut-3-enyl)-N-(2-methylprop-2-enyl)benzenesulfonamide 、 5-methyl-3-methylene-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydropyridine 、 3-methyl-1-(4-toluenesulfonyl)-4-vinyl-2,5-dihydro-1H-pyrrole
  参考文献：
  名称：

  Correlation between Functionality Preference of Ru Carbenes and exo/endo Product Selectivity for Clarifying the Mechanism of Ring-Closing Enyne Metathesis

  摘要：

  Functionality preferences of metathesis Ru carbenes to various alkenes and alkynes with electronic and steric diversity were determined by using time-dependent fluorescence quenching. The functionality preferences depend not only on the properties of multiple bonds but also on the ligands on Ru. There was a good correlation between functionality preference and the metathesis reaction outcome. The correlation between functionality preference and exo/endo product ratio offers a solution to resolve the mechanistic issue related with alkene- vs alkyne-initiated pathway in ring-closing enyne metathesis. The correlation indicates the preference is likely to dictate the reaction pathway and eventually the outcome of the reaction. The Ru catalyst favoring alkyne over alkene provides more endo product, indicating that the reaction mainly initiates at the alkyne. By changing the substitution pattern, the preference can be reversed to give an exclusive exo product.

  DOI：

  10.1021/jo401420f

文献信息

• Correlation between Functionality Preference of Ru Carbenes and <i>exo</i>/<i>endo</i> Product Selectivity for Clarifying the Mechanism of Ring-Closing Enyne Metathesis
  作者：Ok Suk Lee、Kyung Hwan Kim、Jinwoo Kim、Kuktae Kwon、Taedong Ok、Hyotcherl Ihee、Hee-Yoon Lee、Jeong-Hun Sohn

  DOI：10.1021/jo401420f

  日期：2013.9.6

  Functionality preferences of metathesis Ru carbenes to various alkenes and alkynes with electronic and steric diversity were determined by using time-dependent fluorescence quenching. The functionality preferences depend not only on the properties of multiple bonds but also on the ligands on Ru. There was a good correlation between functionality preference and the metathesis reaction outcome. The correlation between functionality preference and exo/endo product ratio offers a solution to resolve the mechanistic issue related with alkene- vs alkyne-initiated pathway in ring-closing enyne metathesis. The correlation indicates the preference is likely to dictate the reaction pathway and eventually the outcome of the reaction. The Ru catalyst favoring alkyne over alkene provides more endo product, indicating that the reaction mainly initiates at the alkyne. By changing the substitution pattern, the preference can be reversed to give an exclusive exo product.