methyl 4-naphthalen-2-yl-6-oxohexa-2,4-dienoate | 1449578-16-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 4-naphthalen-2-yl-6-oxohexa-2,4-dienoate
• CAS: 1449578-16-8
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: ABWQHIDYSCYUGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  methyl 4-naphthalen-2-yl-6-oxohexa-2,4-dienoate 在 氯化铵 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以43%的产率得到methyl 4-(naphthalene-2-yl)picolinate
  参考文献：
  名称：

  A modular approach toward the synthesis of 2,4-disubstituted pyridines

  摘要：

  A number of 2,4-disubstituted pyridines have been synthesized using alpha,beta,gamma,delta-unsaturated aldehydes and ammonium chloride in the presence of triethylamine in acetonitrile solvent at 80 degrees C under air balloon. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.092
• 作为产物：
  描述：

  2-萘乙酮 在 四丁基溴化铵 、 三溴化磷 、 palladium dichloride 作用下， 以 氯仿 、 水 为溶剂， 生成 methyl 4-naphthalen-2-yl-6-oxohexa-2,4-dienoate
  参考文献：
  名称：

  A modular approach toward the synthesis of 2,4-disubstituted pyridines

  摘要：

  A number of 2,4-disubstituted pyridines have been synthesized using alpha,beta,gamma,delta-unsaturated aldehydes and ammonium chloride in the presence of triethylamine in acetonitrile solvent at 80 degrees C under air balloon. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.092

文献信息

• N-Heterocyclic Carbene-Catalyzed δ-Carbon LUMO Activation of Unsaturated Aldehydes
  作者：Tingshun Zhu、Chengli Mou、Baosheng Li、Marie Smetankova、Bao-An Song、Yonggui Robin Chi

  DOI：10.1021/jacs.5b02219

  日期：2015.5.6

  An N-heterocyclic carbene (NHC) catalyzed domino reaction triggered by a delta-LUMO activation of alpha,beta-gamma,delta-diunsaturated enal has been developed for the formal [4 + 2] construction of multisubstituted arenes and 3-ylidenephthalide. These two products, formed in a highly chemo- and regioselective manner, were obtained via different catalytic pathways due to a simple change of the substrate. The activation of the remote delta-carbon of unsaturated aldehydes expands the synthetic potentials of NHC organocatalysis.