trans-N-(4-methoxybenzenesulfonyl)-hex-2-en-1-imine | 903571-08-4

• 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: trans-N-(4-methoxybenzenesulfonyl)-hex-2-en-1-imine
• 英文别名: (NE)-N-[(E)-hex-2-enylidene]-4-methoxybenzenesulfonamide
• CAS: 903571-08-4
• 化学式: C₁₃H₁₇NO₃S
• 分子量: 267.349
• InChiKey: XZPZIPMXUHNENY-IBANSRBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  trans-N-(4-methoxybenzenesulfonyl)-hex-2-en-1-imine 、 反式-4-氧基-2-丁烯酸乙酯 在 chiral N-heterocyclic carbene 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 23.0h， 以58%的产率得到ethyl 2-((3S,4S)-4-(furan-2-yl)-1-(4-methoxyphenylsulfonyl)-2-oxo-1,2,3,4-tetrahydropyridin-3-yl)acetate
  参考文献：
  名称：

  Highly Enantioselective Azadiene Diels−Alder Reactions Catalyzed by Chiral N-Heterocyclic Carbenes

  摘要：

  Highly enantioselective, N-heterocyclic carbene (NHC)-catalyzed aza-Diels-Alder reactions are described. A novel chiral triazolium salt based on the cis-1,2-aminoindanol platform serves as an efficient precatalyst for the NHC-catalyzed redox generation of enolate dienophiles that undergo LUMOdiene-controlled Diels-Alder reactions with N-sulfonyl-alpha,beta-unsaturated imines in good yields and with exceptional diastereo- and enantioselectivities (>99% ee). In contrast to uncatalyzed variants, this organocatalytic process proceeds at room temperature without stoichiometric reagents, producing synthetically valuable, enantiomerically pure cis-3,4-disubstituted dihydropyridinone products.

  DOI：

  10.1021/ja062707c
• 作为产物：
  描述：

  对甲氧基苯磺酰胺 、 反式-2-己烯醛二甲基乙缩醛 反应 0.5h， 生成 trans-N-(4-methoxybenzenesulfonyl)-hex-2-en-1-imine
  参考文献：
  名称：

  Highly Enantioselective Azadiene Diels−Alder Reactions Catalyzed by Chiral N-Heterocyclic Carbenes

  摘要：

  Highly enantioselective, N-heterocyclic carbene (NHC)-catalyzed aza-Diels-Alder reactions are described. A novel chiral triazolium salt based on the cis-1,2-aminoindanol platform serves as an efficient precatalyst for the NHC-catalyzed redox generation of enolate dienophiles that undergo LUMOdiene-controlled Diels-Alder reactions with N-sulfonyl-alpha,beta-unsaturated imines in good yields and with exceptional diastereo- and enantioselectivities (>99% ee). In contrast to uncatalyzed variants, this organocatalytic process proceeds at room temperature without stoichiometric reagents, producing synthetically valuable, enantiomerically pure cis-3,4-disubstituted dihydropyridinone products.

  DOI：

  10.1021/ja062707c

文献信息

• ENANTIOSELECTIVE REACTIONS CATALYZED BY CHIRAL TRIAZOLIUM SALTS
  申请人：Bode Jeffrey

  公开号：US20100210452A1

  公开（公告）日：2010-08-19

  This invention provides a convenient method for converting imines and other electrophiles into heterocyclic ring systems. The process does not require the use of metallic reagents, and is catalyzed by an organic heterocyclic carbene catalyst. Accordingly, it produces the desired compounds without the concomitant production of a large volume of metallic waste. Chiral heterocyclic carbene catalysts of the invention and methods of using these catalysts produce chiral heterocycles in high enantiomeric and diastereomeric excess.

  本发明提供了一种将亚胺和其他亲电试剂转化为杂环环系统的方便方法。该过程不需要使用金属试剂，而是由有机杂环卡宾催化剂催化。因此，它可产生所需化合物而不伴随大量金属废物的产生。本发明的手性杂环卡宾催化剂及其使用方法可产生高对映选择性和立体异构选择性的手性杂环。
• US8501658B2
  申请人：——

  公开号：US8501658B2

  公开（公告）日：2013-08-06
• [EN] ENANTIOSELECTVE REACTIONS CATALYZED BY CHIRAL TRIAZOLIUM SALTS<br/>[FR] RÉACTION ÉNANTIOSÉLECTIVE CATALYSÉE PAR DES SELS DE TRIAZOLIUM CHIRAUX
  申请人：UNIV CALIFORNIA

  公开号：WO2007124494A2

  公开（公告）日：2007-11-01

  [EN] This invention provides a convenient method for converting imines and other electrophiles into heterocyclic ring systems. The process does not require the use of metallic reagents, and is catalyzed by an organic heterocyclic carbene catalyst. Accordingly, it produces the desired compounds without the concomitant production of a large volume of metallic waste. Chiral heterocyclic carbene catalysts of the invention and methods of using these catalysts produce chiral heterocycles in high enantiomeric and diastereomeric excess.
  [FR] La présente invention concerne une méthode pratique de conversion d'imines et d'autres électrophiles en systèmes hétérocycliques. Le procédé ne nécessite pas l'utilisation de réactifs métalliques, et est catalysé par un catalyseur carbène hétérocyclique organique. Ainsi, il produit les composés recherchés sans production concomitante d'un volume important de déchets métalliques. Les catalyseurs de carbène hétérocycliques chiraux selon l'invention et les méthodes d'emploi de ces catalyseurs permettent d'obtenir des hétérocycles chiraux avec des excès énantiomériques et diastéréomériques élevés.
• Highly Enantioselective Azadiene Diels−Alder Reactions Catalyzed by Chiral N-Heterocyclic Carbenes
  作者：Ming He、Justin R. Struble、Jeffrey W. Bode

  DOI：10.1021/ja062707c

  日期：2006.7.1

  Highly enantioselective, N-heterocyclic carbene (NHC)-catalyzed aza-Diels-Alder reactions are described. A novel chiral triazolium salt based on the cis-1,2-aminoindanol platform serves as an efficient precatalyst for the NHC-catalyzed redox generation of enolate dienophiles that undergo LUMOdiene-controlled Diels-Alder reactions with N-sulfonyl-alpha,beta-unsaturated imines in good yields and with exceptional diastereo- and enantioselectivities (>99% ee). In contrast to uncatalyzed variants, this organocatalytic process proceeds at room temperature without stoichiometric reagents, producing synthetically valuable, enantiomerically pure cis-3,4-disubstituted dihydropyridinone products.