3-(3,4-difluorophenyl)propiolaldehyde

• 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: 3-(3,4-difluorophenyl)propiolaldehyde
• 英文别名: 3-(3,4-Difluorophenyl)prop-2-ynal；3-(3,4-difluorophenyl)prop-2-ynal
• 化学式: C₉H₄F₂O
• 分子量: 166.127
• InChiKey: VQEASGQIMBZAJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3,4-difluorophenyl)propiolaldehyde 、 N-乙酰乙酰苯胺 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以89%的产率得到3-acetyl-4-(3,4-difluorophenyl)-1-phenylpyridin-2(1H)-one
  参考文献：
  名称：

  由β-酮酰胺和ynals无过渡金属高效合成2-吡啶酮

  摘要：

  开发了一种方便而有效的环化反应，以良好的产率获得了2-吡啶酮。多种取代的β-酮酰胺和ynal具有良好的耐受性，尤其是在无过渡金属的条件下，该转化产生的水仅作为副产物。此外，从β-氰基酰胺和ynals以高收率获得了共轭烯炔酰胺。

  DOI：

  10.1016/j.tetlet.2019.04.001
• 作为产物：
  描述：

  1,2-二氟-4-碘代苯 在 manganese(IV) oxide 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 3-(3,4-difluorophenyl)propiolaldehyde
  参考文献：
  名称：

  Catalyst-Free Annulation of 2-Pyridylacetates and Ynals with Molecular Oxygen: An Access to 3-Acylated Indolizines

  摘要：

  A catalyst and additive-free annulation of 2-pyridylacetates and ynals under molecular oxygen was the first developed, affording 3-acylated indolizines in good to excellent yields. Molecular oxygen was used as the source of the carbonyl oxygen atom in indolizines. This approach was compatible with a wide range of functional groups, and especially it has been successfully extended to unsaturated double bonds and triple bonds, which were difficult to prepare by previous methods in a single step.

  DOI：

  10.1021/acs.joc.8b02883

文献信息

• Lewis Acid-Catalyzed Intermolecular Annulation: Three-Component Reaction toward Imidazo[1,2-<i>a</i>]pyridine Thiones
  作者：Zhengwang Chen、Pei Liang、Fan Xu、Rulin Qiu、Qi Tan、Lipeng Long、Min Ye

  DOI：10.1021/acs.joc.9b01188

  日期：2019.7.19

  A Lewis acid-catalyzed three-component annulation reaction of 2-aminopyridines and ynals with elemental sulfur was established. A series of imidazo[1,2-a]pyridine thiones was obtained in moderate to excellent yields. The merits of this transformation include easily available starting materials, multiple C-heteroatom bond formation in one pot, good functional group tolerance, elemental sulfur as S source

  建立了路易斯酸催化的2-氨基吡啶和ynals与元素硫的三组分环化反应。以中等至优异的产率获得了一系列咪唑并[1,2- a ]吡啶硫酮。这种转化的优点包括：容易获得的起始原料，在一个罐中形成多个C-杂原子键，良好的官能团耐受性，元素硫作为S源，操作简便等。
• Catalyst-Free Annulation of 2-Pyridylacetates and Ynals with Molecular Oxygen: An Access to 3-Acylated Indolizines
  作者：Zhengwang Chen、Pei Liang、Xiaoyue Ma、Haiqing Luo、Guohai Xu、Tanggao Liu、Xiaowei Wen、Jing Zheng、Hui Ye

  DOI：10.1021/acs.joc.8b02883

  日期：2019.2.1

  A catalyst and additive-free annulation of 2-pyridylacetates and ynals under molecular oxygen was the first developed, affording 3-acylated indolizines in good to excellent yields. Molecular oxygen was used as the source of the carbonyl oxygen atom in indolizines. This approach was compatible with a wide range of functional groups, and especially it has been successfully extended to unsaturated double bonds and triple bonds, which were difficult to prepare by previous methods in a single step.
• Transition-metal-free highly efficient synthesis of 2-pyridones from β-keto amides and ynals
  作者：Zhengwang Chen、Jiayang Liu、Caiju Jin、Qi Tan、Min Ye

  DOI：10.1016/j.tetlet.2019.04.001

  日期：2019.5

  A convenient and efficient annulation reaction was developed, affording 2-pyridones in good to excellent yields. A variety of substituted β-keto amides and ynals were well tolerated, and especially the transformation produced water as only by-product under transition-metal-free conditions. Furthermore, the conjugated enyneamides were achieved from β-cyano amides and ynals in high yields.

  开发了一种方便而有效的环化反应，以良好的产率获得了2-吡啶酮。多种取代的β-酮酰胺和ynal具有良好的耐受性，尤其是在无过渡金属的条件下，该转化产生的水仅作为副产物。此外，从β-氰基酰胺和ynals以高收率获得了共轭烯炔酰胺。