(R)-6-phenyl-4-(thiophen-2-yl)-1-tosyl-3,4-dihydropyridin-2(1H)-one

• 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: (R)-6-phenyl-4-(thiophen-2-yl)-1-tosyl-3,4-dihydropyridin-2(1H)-one
• 英文别名: (4R)-1-(4-methylphenyl)sulfonyl-6-phenyl-4-thiophen-2-yl-3,4-dihydropyridin-2-one
• 化学式: C₂₂H₁₉NO₃S₂
• 分子量: 409.53
• InChiKey: UXSJLGCQFFYUGC-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  91.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-methyl-N-(1-phenyl-3-(thiophen-2-yl)allylidene)benzenesulfonamide 、 4-硝基苯基乙酸酯 在 BF₄^(1-)*C₂₁H₂₄N₃O⁽¹⁺⁾ 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以63%的产率得到(R)-6-phenyl-4-(thiophen-2-yl)-1-tosyl-3,4-dihydropyridin-2(1H)-one
  参考文献：
  名称：

  Asymmetric Access to the Smallest Enolate Intermediate via Organocatalytic Activation of Acetic Ester

  摘要：

  An NHC-catalyzed activation of acetic esters to afford enolate intermediates is disclosed. The catalytically generated triazolium enolate intermediates serve as two-carbon nucleophiles that undergo highly enantioselective reactions with enones and alpha,beta-unsaturated imines to give a-unsubstituted delta-lactones and lactams, respectively.

  DOI：

  10.1021/ol402877n

文献信息

• Enantioselective N-Heterocyclic Carbene-Catalyzed [3+3] Annulation of α,β-Unsaturated Esters with Methyl Ketoimine
  作者：Wenjing Xia、Hong Yao、Dan Liu、Linxiang Zhao、Yu Zhou、Hong Liu

  DOI：10.1002/adsc.201600136

  日期：2016.6.2

  carbene (NHC)‐catalyzed [3+3] annulation of challenging esters with methyl ketoimines for the highly enantioselective synthesis of intriguing δ‐lactams featuring various substituent patterns. The annulation occurs under mild conditions and offers good tolerance, good yields and excellent enantioselectivities. The six‐membered heterocyclic products are valuable for the synthesis of bioactive molecules

  本文中，我们公开了N-杂环卡宾（NHC）催化的具有挑战性的酯与甲基酮亚胺的[3 + 3]环化反应，用于具有各种取代基图案的有趣δ-内酰胺的高度对映选择性合成。该成环在温和的条件下发生，并提供良好的耐受性，良好的产率和优异的对映选择性。六元杂环产物对于生物活性分子的合成很有价值。
• Asymmetric Access to the Smallest Enolate Intermediate via Organocatalytic Activation of Acetic Ester
  作者：Shaojin Chen、Lin Hao、Yuexia Zhang、Bhoopendra Tiwari、Yonggui Robin Chi

  DOI：10.1021/ol402877n

  日期：2013.11.15

  An NHC-catalyzed activation of acetic esters to afford enolate intermediates is disclosed. The catalytically generated triazolium enolate intermediates serve as two-carbon nucleophiles that undergo highly enantioselective reactions with enones and alpha,beta-unsaturated imines to give a-unsubstituted delta-lactones and lactams, respectively.