6-methyl-2-(3-phenoxyprop-1-yn-1-yl)quinoline-3-carbaldehyde | 1434153-26-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-methyl-2-(3-phenoxyprop-1-yn-1-yl)quinoline-3-carbaldehyde
• CAS: 1434153-26-0
• 化学式: C₂₀H₁₅NO₂
• 分子量: 301.345
• InChiKey: SFCKDHRPUGGBDF-UHFFFAOYSA-N

物化性质

• 沸点：
  521.6±50.0 °C(predicted)
• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  39.19
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-methyl-2-(3-phenoxyprop-1-yn-1-yl)quinoline-3-carbaldehyde 在 碘 、 sodium acetate 、 palladium diacetate 、 potassium carbonate 、 lithium chloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 1,2-bis(4-methoxyphenyl)-8-methyl-4-phenoxy-3H-pyrrolo-[3,2,1-de]acridin-3-one
  参考文献：
  名称：

  Tandem Synthesis of Pyrroloacridones via [3 + 2] Alkyne Annulation/Ring-Opening with Concomitant Intramolecular Aldol Condensation

  摘要：

  An efficient cascade strategy for the direct synthesis of pyrrolo[3,2,1-de]acridones 4a-v, 5a-h from iodopyranoquinolines 2a-i by the palladium-catalyzed regioselective [3 + 2] alkyne annulation/ring-opening followed by intramolecular aldol condensation under microwave irradiation is described. The chemistry involves the in situ formation of pyrroloquinolines Y, via palladium-catalyzed selective [3 + 2] annulation of iodopyranoquinolines and internal akynes with ring-opening and successive intramolecular cross-aldol condensation. Both the symmetrical and unsymmetrical internal alkynes were reacted smoothly to provide the desired pyrroloacridones in good yields. This methodology provides the facile conversion of easily accessble iodopyranoquinoline into highly functionalized biologically important pyrroloacridones in a single process.

  DOI：

  10.1021/jo400539x

文献信息

• Highly Selective Synthesis of α-Hydroxy, α-Oxy, and α-Oxo Amides by a Post-Passerini Condensation Transformation
  作者：Morteza Shiri、Zahra Gholami-Koupaei、Farzaneh Bandehali-Naeini、Maryam-Sadat Tonekaboni、Saeedeh Soheil-Moghaddam、Delaram Ebrahimi、Sima Karami、Behrouz Notash

  DOI：10.1055/s-0040-1707132

  日期：2020.11

  Published as part of the Special Topic Recent Advances in Amide Bond Formation Abstract A post-Passerini condensation transformation can be employed in the synthesis of three types of amides: α-hydroxy, α-oxy, and α-oxo amides. K2CO3 efficiently promotes the solvolysis of α-acetoxy amides to form α-hydroxy amides in methanol. 2-Acetoxy-2-(2-alkynyl­quinolin-3-yl)acetamides in basic methanol are cyclized

  作为特别主题的一部分发表，酰胺键形成的最新进展 抽象 Passerini后缩合转化可用于合成三种类型的酰胺：α-羟基，α-氧基和α-氧代酰胺。K 2 CO 3有效地促进α-乙酰氧基酰胺的溶剂分解以在甲醇中形成α-羟基酰胺。碱性甲醇中的2-乙酰氧基-2-（2-炔基喹啉-3-基）乙酰胺通过脱乙酰基作用和5- exo - dig环化作用环化为1,3-二氢呋喃[3,4- b ]喹啉-1-羧酰胺。在碱性介质中用I 2处理2-羟基-2- [2-（苯基乙炔基）喹啉-3-基]乙酰胺产生吡咯并[2,3- b]喹啉-2,3-二酮。该环化涉及分子内环化，脱炔基芳构化和仲醇的氧化。