(E)-2-(naphthalen-2-yl)but-2-enal | 1085339-95-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-2-(naphthalen-2-yl)but-2-enal
• 英文别名: (E)-2-naphthalen-2-ylbut-2-enal
• CAS: 1085339-95-2
• 化学式: C₁₄H₁₂O
• 分子量: 196.249
• InChiKey: QLCSNZXTYYLTGW-FUQNDXKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  4-(naphthalen-2-yl)-4-vinyl-1,3-dioxolan-2-one 在 [1,2-bis-(phenylsulfinyl)ethane]palladium(II) acetate 、 双(2-二苯基磷苯基)醚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以98%的产率得到
  参考文献：
  名称：

  A Domino Process toward Functionally Dense Quaternary Carbons through Pd-Catalyzed Decarboxylative C(sp³)–C(sp³) Bond Formation

  摘要：

  An efficient protocol was developed to construct functionally dense quaternary carbons with concomitant formation of a new Csp(3)-Csp(3) bond via Pd-catalyzed decarboxylative transformation of vinyl cyclic carbonates. This redox-neutral catalytic system features stereocontrolled formation of multisubstituted allylic scaffolds with an aldehyde functionality generated in situ, and it typically can be performed at room temperature without any additives. DFT calculations provide a rationale toward the selective formation of these compounds and reveal a complex mechanism that with the help of microkinetic models is able to reproduce the nontrivial dependence of the identity of the product on the nature of the substituents in the substrate.

  DOI：

  10.1021/jacs.7b12608

文献信息

• Palladium-catalysed Heck reaction on 1,2-dien-1-ols: a stereoselective synthesis of α-arylated α,β-unsaturated aldehydes
  作者：Annamaria Deagostino、Cristina Prandi、Antonio Toppino、Paolo Venturello

  DOI：10.1016/j.tet.2008.08.081

  日期：2008.11

  A new methodology for preparing alpha-arylated alpha,beta-unsaturated aldehydes is reported. The starting materials are all commercially available alkyn-1-ols (la-c) that have been easily isomerised to the corresponding allenes (2a-c). The key step is the Heck coupling of the 1,2-dien-1-ols with a series of iodo- and bromoarene. The products have been synthesised in good yields, and the reactions were carried out under very mild conditions. (C) 2008 Elsevier Ltd. All rights reserved.