(E)-1,3-diphenyl-N-(4-methoxyphenylsulfonyl)prop-2-en-1-imine

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1,3-diphenyl-N-(4-methoxyphenylsulfonyl)prop-2-en-1-imine
• 英文别名: (NZ)-N-[(E)-1,3-diphenylprop-2-enylidene]-4-methoxybenzenesulfonamide
• 化学式: C₂₂H₁₉NO₃S
• 分子量: 377.464
• InChiKey: SKIJHJCNSZIGQU-YZVBRHGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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)-1,3-diphenyl-N-(4-methoxyphenylsulfonyl)prop-2-en-1-imine 在 5-benzyl-2-phenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 sodium tetrahydroborate 、 N,N-二异丙基乙胺 、 邻苯三酚 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  cis-Enals in N-heterocyclic carbene-catalyzed reactions: distinct stereoselectivity and reactivity

  摘要：

  在 N-heterocyclic carbenes (NHC) 催化下，首次成功地从顺式烯烃中生成了顺式高烯酸酯。顺式烯醇中间体与 α、β-不饱和亚胺发生有效反应，生成手性环酮产物。与反式烯醛相比，顺式烯醛显示出不同的立体选择性和新的反应模式。

  DOI：

  10.1039/c3sc50666e
• 作为产物：
  描述：

  对甲氧基苯磺酰胺 、 反式-查耳酮 在 四氯化钛 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-1,3-diphenyl-N-(4-methoxyphenylsulfonyl)prop-2-en-1-imine
  参考文献：
  名称：

  Enantioselective, NHC-Catalyzed Bicyclo-β-Lactam Formation via Direct Annulations of Enals and Unsaturated N-Sulfonyl Ketimines

  摘要：

  A wide range of alpha,beta-unsaturated aldehydes induding 3-alkyl derivatives undergo N-heterocyclic carbene (NHC)-catalyzed annulations with N-sulfonyl ketimines under mild condition, to provide bicyclo[3.2.0]lactams with outstanding diastereo- and enantioselectivity. This concise route to beta-lactams established four new chiral centers in a single operation. Although this process could occur via the intermediacy of a catalytically generated homoenolate equivalent, the stereochemical outcome supports a tandem or concerted aza-Benzoin/oxy-Cope reaction as the key bond forming step.

  DOI：

  10.1021/ja0778592

文献信息

• Enantioselective, NHC-Catalyzed Bicyclo-β-Lactam Formation via Direct Annulations of Enals and Unsaturated <i>N</i>-Sulfonyl Ketimines
  作者：Ming He、Jeffrey W. Bode

  DOI：10.1021/ja0778592

  日期：2008.1.1

  A wide range of alpha,beta-unsaturated aldehydes induding 3-alkyl derivatives undergo N-heterocyclic carbene (NHC)-catalyzed annulations with N-sulfonyl ketimines under mild condition, to provide bicyclo[3.2.0]lactams with outstanding diastereo- and enantioselectivity. This concise route to beta-lactams established four new chiral centers in a single operation. Although this process could occur via the intermediacy of a catalytically generated homoenolate equivalent, the stereochemical outcome supports a tandem or concerted aza-Benzoin/oxy-Cope reaction as the key bond forming step.
• cis-Enals in N-heterocyclic carbene-catalyzed reactions: distinct stereoselectivity and reactivity
  作者：Xingkuan Chen、Xinqiang Fang、Yonggui Robin Chi

  DOI：10.1039/c3sc50666e

  日期：——

  The first successful generation of cis-homoenolate equivalents from cis-enals under the catalysis of N-heterocyclic carbenes (NHCs) has been realized. The cis-homoenolate intermediates undergo effective reactions with α,β-unsaturated imines to afford chiral cyclic ketone products. Compared to the trans-enals, cis-enals show different stereoselectivities and new reactivity patterns.

  在 N-heterocyclic carbenes (NHC) 催化下，首次成功地从顺式烯烃中生成了顺式高烯酸酯。顺式烯醇中间体与 α、β-不饱和亚胺发生有效反应，生成手性环酮产物。与反式烯醛相比，顺式烯醛显示出不同的立体选择性和新的反应模式。