benzyl (E)-4-(4-methylphenyl)-2-oxobut-3-enoate | 1330533-27-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: benzyl (E)-4-(4-methylphenyl)-2-oxobut-3-enoate
• CAS: 1330533-27-1
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: GLFUJJRCKFVIKH-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl (E)-4-(4-methylphenyl)-2-oxobut-3-enoate 、 N-(2-ethynylbenzyl)-4-methylbenzenesulfonamide 在 1,3-双(2,6-二-异丙基苯基)咪唑-2-亚基金(I)氯化物 、 silver trifluoromethanesulfonate 、 lanthanum(lll) triflate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以87%的产率得到benzyl (3S,4'R)-4'-(4-methylphenyl)-2-(4-methylphenyl)sulfonylspiro[1H-isoindole-3,2'-3,4-dihydropyran]-6'-carboxylate
  参考文献：
  名称：

  Synthesis of Spiroaminals and Spiroketals with Bimetallic Relay Catalysis

  摘要：

  A novel tandem metal relay catalytic system was developed by combining gold-catalyzed cycloisomerization with an early transition-metal-catalyzed inverse-electron-demand hetero-Diels-Alder (IED-HDA) reaction. Various biologically important spiroaminals and spiroketals were obtained with very high efficiency under mild conditions.

  DOI：

  10.1021/ol4033286

文献信息

• Chiral Sulfinamide-Olefin Ligands: Switchable Selectivity in Rhodium-Catalyzed Asymmetric 1,2-Addition of Arylboronic Acids to Aliphatic<i>α</i>-Ketoesters
  作者：Ting-Shun Zhu、Ming-Hua Xu

  DOI：10.1002/cjoc.201300063

  日期：2013.3

  es have been developed as efficient novel ligands for the rhodium‐catalyzed enantioselective 1,2‐addition of arylboronic acids to challenging aliphatic α‐ketoesters. By employing the linear or branched sulfinamide‐olefin ligands, interesting enantioselectivity as well as regioselectivity reversal in the related asymmetric additions were observed.

  已开发出简单易用的手性N-（亚磺酰基）烯丙胺作为有效的新型配体，用于铑催化的对芳基硼酸对映选择性1,2-芳构酸加成，以取代具有挑战性的脂族α-酮酸酯。通过使用线性或支链的亚磺酰胺-烯烃配体，在相关的不对称添加物中观察到有趣的对映选择性和区域选择性逆转。
• Organocatalytic Asymmetric Formal [3+3]‐Cycloaddition to Access 2,3‐Diazaspiro[4.5]deca‐3,6‐dien‐1‐ones
  作者：A. Vamshi Krishna、G. Surendra Reddy、B. Gorachand、Dhevalapally B. Ramachary

  DOI：10.1002/ejoc.202001175

  日期：2020.11.15

  Single structure out of many domino reactions! Double sequence of isoaromatization and dearomatization driven the domino Michael/aldol or formal [3+3]‐cycloaddition as an efficient tool for the construction of chiral drug‐like 2,3‐diazaspiro[4.5]deca‐3,6‐dien‐1‐ones having spirocyclic vicinal quaternary carbon centers.

  许多多米诺骨牌反应中只有一个结构！异芳香化和脱芳香化的双重序列驱动了多米诺骨牌Michael / aldol或正式的[3 + 3]-环加成反应，作为构建手性药物样2,3-二氮杂螺[4.5] deca-3,6-dien-1的有效工具-具有螺环邻位季碳中心的化合物。