(E)-4-methoxy-N-((E)-p-tolylethylidene)benzenesulfonamide | 861145-19-9

• 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)-4-methoxy-N-((E)-p-tolylethylidene)benzenesulfonamide
• 英文别名: (E)-4-methoxy-N-(4-methylbenzylidene)benzenesulfonamide；(NE)-4-methoxy-N-[(4-methylphenyl)methylidene]benzenesulfonamide
• CAS: 861145-19-9
• 化学式: C₁₅H₁₅NO₃S
• 分子量: 289.355
• InChiKey: WGFYPBYQCZYSFZ-LFIBNONCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  64.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-4-methoxy-N-((E)-p-tolylethylidene)benzenesulfonamide 、 2-萘基丙烯酸酯 在 N-((2S,3R)-3-((2,3-dimethylbutan-2-yl)dimethylsilyloxy)-1-(diphenylphosphino)butan-2-yl)-4-methylbenzenesulfonamide 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以91%的产率得到(R)-naphthalen-2-yl 2-((4-methoxyphenylsulfonamido)(p-tolyl)methyl)acrylate
  参考文献：
  名称：

  l-Threonine-Derived Novel Bifunctional Phosphine−Sulfonamide Catalyst-Promoted Enantioselective Aza-Morita−Baylis−Hillman Reaction

  摘要：

  A series of novel bifunctional phosphine sulfonamide organic catalysts were designed and readily prepared from natural amino acids, and they were utilized to promote enantioselective aza-Morita-Baylis-Hillman (MBH) reactions. L-Threonine-derived phosphine-sulfonamide 9b was found to be the most efficient catalyst, affording the desired aza-MBH adducts in high yields and with excellent enantioselectivities.

  DOI：

  10.1021/ol103145g
• 作为产物：
  描述：

  1-(二甲氧基甲基)-4-甲基苯 、 对甲氧基苯磺酰胺 反应 0.5h， 生成 (E)-4-methoxy-N-((E)-p-tolylethylidene)benzenesulfonamide
  参考文献：
  名称：

  Catalytic Synthesis of γ-Lactams via Direct Annulations of Enals and N-Sulfonylimines

  摘要：

  Cinnamaldehydes and N-sulfonylimines undergo direct annulations to cis-disubstituted gamma-lactams via the intermediacy of catalytically generated homoenolates. Critical to the success of this process was overcoming inhibition of the N-heterocyclic carbene catalyst by the electrophilic imines. The overall process proceeds with good yields and diastereoselectivites and requires no stoichiometric reagents or additives.

  DOI：

  10.1021/ol051234w

文献信息

• Pendant Alkoxy Groups on N‐Aryl Substitutions Drive the Efficiency of Imidazolylidene Catalysts for Homoenolate Annulation from Enal and Aldehyde
  作者：Ryuji Kyan、Kohei Sato、Nobuyuki Mase、Tetsuo Narumi

  DOI：10.1002/anie.202008631

  日期：2020.10.19

  a critical step affecting the efficiency of the NHC‐catalyzed γ‐butyrolactone formation via homoenolate addition to aryl aldehydes. A novel type of imidazolylidene catalyst with pendant alkoxy groups on the ortho‐N‐aryl groups is described. Catalyst of this sort facilitates the formation of the conjugated Breslow intermediate. Studies of the rate constants for homoenolate annulation affording γ‐butyrolactones

  由咪唑基亚烷基催化剂和α，β-不饱和醛在四面体中间体中进行的氢转移形成了共轭Breslow中间体。这是关键步骤，它通过向芳基醛中添加均烯酸酯来影响NHC催化的γ-丁内酯的形成效率。一种新型的邻位烷氧基侧基的咪唑基亚烷基催化剂描述了-N-芳基。这种催化剂有助于形成共轭的Breslow中间体。对提供γ-丁内酯的均烯酸酯环化反应速率常数的研究表明，在N-芳基取代基的适当位置引入氧原子可以提高咪唑基亚烷基催化剂的效率。结构和机理研究表明，烷氧基侧基可以靠近四面体中间体的质子，从而促进质子转移。
• Synthesis of an <i>N</i>-Mesityl Substituted Chiral Imidazolium Salt for NHC-Catalyzed Reactions
  作者：Justin R. Struble、Juthanat Kaeobamrung、Jeffrey W. Bode

  DOI：10.1021/ol800006m

  日期：2008.3.1

  A new synthetic approach to chiral imidazolium salts makes possible the first synthesis of an N-mesityl substituted, aminoindanol-derived N-heterocyclic carbene precursor, 1.ClO4. The successful synthesis allows the first direct comparison of otherwise identical imidazolium and triazolium precursors across a number of NHC-catalyzed processes. These studies confirm striking differences in reactivity

  一种新的手性咪唑鎓盐合成方法，使得首次合成N-间苯二甲酰基取代的氨基茚满醇衍生的N-杂环卡宾前体1.ClO4成为可能。成功的合成方法可以在许多NHC催化过程中首次直接比较在其他方面相同的咪唑鎓和三唑鎓前体。这些研究证实了这两类药物在反应性和机理上的显着差异。
• Catalytic Synthesis of γ-Lactams via Direct Annulations of Enals and <i>N</i>-Sulfonylimines
  作者：Ming He、Jeffrey W. Bode

  DOI：10.1021/ol051234w

  日期：2005.7.1

  Cinnamaldehydes and N-sulfonylimines undergo direct annulations to cis-disubstituted gamma-lactams via the intermediacy of catalytically generated homoenolates. Critical to the success of this process was overcoming inhibition of the N-heterocyclic carbene catalyst by the electrophilic imines. The overall process proceeds with good yields and diastereoselectivites and requires no stoichiometric reagents or additives.
• <scp>l</scp>-Threonine-Derived Novel Bifunctional Phosphine−Sulfonamide Catalyst-Promoted Enantioselective Aza-Morita−Baylis−Hillman Reaction
  作者：Fangrui Zhong、Youqing Wang、Xiaoyu Han、Kuo-Wei Huang、Yixin Lu

  DOI：10.1021/ol103145g

  日期：2011.3.18

  A series of novel bifunctional phosphine sulfonamide organic catalysts were designed and readily prepared from natural amino acids, and they were utilized to promote enantioselective aza-Morita-Baylis-Hillman (MBH) reactions. L-Threonine-derived phosphine-sulfonamide 9b was found to be the most efficient catalyst, affording the desired aza-MBH adducts in high yields and with excellent enantioselectivities.