(E)-1-formyl-2-[2-(1-naphthyl)ethenyl]benzene | 1220094-29-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-1-formyl-2-[2-(1-naphthyl)ethenyl]benzene
• CAS: 1220094-29-0
• 化学式: C₁₉H₁₄O
• 分子量: 258.32
• InChiKey: QZILHCVTJBXCLJ-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  肌氨酸 、 (E)-1-formyl-2-[2-(1-naphthyl)ethenyl]benzene 以 四氢呋喃 为溶剂， 反应 12.0h， 以69%的产率得到2,3-dihydro-4-(1-naphthyl)-2-methyl-1H-2-benzazepine
  参考文献：
  名称：

  An investigation of the scope of the 1,7-electrocyclization of α,β:γ,δ-conjugated azomethine ylides

  摘要：

  Substituents on the diene component have little influence on the periselectivity of the cyclizations of alpha,beta:gamma,delta-conjugated azomethine ylides, with 1,7-electrocyclizations predominating. In some cases, subtle changes to these substituents can, however, influence the product formed, through their effect on the relative energies of the transition states for the 1,5- (6 pi) and 1,7-electrocyclization (8 pi) processes. The most striking changes in periselectivity occur for phenylethenyl-substituted azomethine ylides 3d-f, which can give either a pyrroline 4d,f or dihydrobenzazepine 6e, depending upon the alkene configuration. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.078
• 作为产物：
  描述：

  [(2-溴苯基)甲基]三苯基-鏻溴化物 在 正丁基锂 、 碘 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 正庚烷 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 52.75h， 生成 (E)-1-formyl-2-[2-(1-naphthyl)ethenyl]benzene
  参考文献：
  名称：

  An investigation of the scope of the 1,7-electrocyclization of α,β:γ,δ-conjugated azomethine ylides

  摘要：

  Substituents on the diene component have little influence on the periselectivity of the cyclizations of alpha,beta:gamma,delta-conjugated azomethine ylides, with 1,7-electrocyclizations predominating. In some cases, subtle changes to these substituents can, however, influence the product formed, through their effect on the relative energies of the transition states for the 1,5- (6 pi) and 1,7-electrocyclization (8 pi) processes. The most striking changes in periselectivity occur for phenylethenyl-substituted azomethine ylides 3d-f, which can give either a pyrroline 4d,f or dihydrobenzazepine 6e, depending upon the alkene configuration. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.078

文献信息

• Iodine‐Catalyzed Cascade Reaction of 2‐Styrylbenzaldehydes with Indoles in the Synthesis of 1<i>H</i>‐Indenes via 4π‐Electrocyclization
  作者：Sundaram Suresh、Hao‐Yu Tsai、Xin‐Lun Han、Veerababurao Kavala、Sowndarya Palla、Ching‐Fa Yao

  DOI：10.1002/adsc.202301412

  日期：2024.3.19

  A cascade reaction between 2-styrylbenzaldehydes and indoles has been developed for the synthesis of 1H-indenes. An iodine-catalyzed nucleophilic addition of indoles to an aldehyde group of 2-styrylbenzaldehydes leads to the formation of carbocation intermediates that undergo 4π-electrocyclization to give indenes with a trisubstituted double bond. These indenes are transformed into thermodynamically

  2-苯乙烯基苯甲醛和吲哚之间的级联反应已被开发用于合成 1H-茚。碘催化吲哚与 2-苯乙烯基苯甲醛的醛基发生亲核加成，形成碳正离子中间体，该中间体经历 4π 电环化，得到具有三取代双键的茚。这些茚在反应条件下转化为热力学上更稳定的具有完全取代双键的产物。还产生少量的吲哚基苯并[b]咔唑副产物。