2-[N-4-Methylphenyl-N-(prop-2-ynyl)]aminochromone-3-carbaldehyde | 1522093-40-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-[N-4-Methylphenyl-N-(prop-2-ynyl)]aminochromone-3-carbaldehyde
• CAS: 1522093-40-8
• 化学式: C₂₀H₁₅NO₃
• 分子量: 317.344
• InChiKey: WPGHMIWMAWOHEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  50.52
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-[N-4-Methylphenyl-N-(prop-2-ynyl)]aminochromone-3-carbaldehyde 在 copper(l) iodide 、 碘 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以60%的产率得到1-(4-Methylphenyl)-1,2-dihydrochromeno[2,3-b]azepine-3,6-dione
  参考文献：
  名称：

  Iodine/CuI-mediated alkyne–carbonyl metathesis reaction: synthesis of 1-aryl-1,2-dihydrochromeno[2,3-b]azepine-3,6-dione

  摘要：

  Iodine/cuprous iodide-mediated intramolecular alkyne carbonyl metathesis reaction has been developed using 2,-(N-aryl-N-propargyl)aminochromone-3-carbaldehyde as the substrate. It led to the synthesis of hitherto unreported chromeno[2,3-b]azepine-3,6-dione. The special features of this methodology are mild reaction conditions, 100% atom economy and use of inexpensive reagents. This is the first example of I-2/Cul-mediated alkyne carbonyl metathesis reaction. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.062
• 作为产物：
  描述：

  3-溴丙炔 、 2-(p-tolylamino)-3-formylchromone 在 potassium carbonate 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 7.0h， 以58%的产率得到2-[N-4-Methylphenyl-N-(prop-2-ynyl)]aminochromone-3-carbaldehyde
  参考文献：
  名称：

  Iodine/CuI-mediated alkyne–carbonyl metathesis reaction: synthesis of 1-aryl-1,2-dihydrochromeno[2,3-b]azepine-3,6-dione

  摘要：

  Iodine/cuprous iodide-mediated intramolecular alkyne carbonyl metathesis reaction has been developed using 2,-(N-aryl-N-propargyl)aminochromone-3-carbaldehyde as the substrate. It led to the synthesis of hitherto unreported chromeno[2,3-b]azepine-3,6-dione. The special features of this methodology are mild reaction conditions, 100% atom economy and use of inexpensive reagents. This is the first example of I-2/Cul-mediated alkyne carbonyl metathesis reaction. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.062

文献信息

• Design and synthesis of dichromeno[2,3-b;3′,2′-e]pyridine-12,14-dione to evaluate its optical properties
  作者：Pritam Biswas、Jaydip Ghosh、Tapas Sarkar、Debabrata Jana、Chandrakanta Bandyopadhyay

  DOI：10.1039/c6nj04057h

  日期：——

  An unambiguous synthesis of dichromeno[2,3-b;3′,2′-e]pyridine-12,14-diones has been developed under mild conditions and their optical properties have been evaluated by studying UV-vis absorption and photoluminescence (PL) spectroscopy, cyclic voltammetry (CV) measurements, DFT calculations and thermogravimetric analysis.

  已开发了在温和条件下双色[2,3- b ; 3'，2' - e ]吡啶-12,14-二酮的明确合成方法，并且通过研究紫外可见吸收和光致发光（PL）评估了它们的光学性质光谱，循环伏安（CV）测量，DFT计算和热重分析。
• Amine-Controlled Reduction of 2-Aminochromone-3-Carbaldehyde with Zn and Acetic Acid
  作者：Pritam Biswas、Jaydip Ghosh、Tapas Sarkar、Chandrakanta Bandyopadhyay

  DOI：10.3184/174751915x14477880702453

  日期：2015.12

  On heating with zinc in acetic acid 2-(N-arylamino)chromone-3-carbaldehydes produce 2-(N-arylamino)-3-methylchromones, whereas 2-(N-alkylamino)chromone-3-carbaldehydes produce 4-hydroxy-3-methylcoumarin in moderate yields. Reduction of an aldehyde function to a methyl group has been achieved under very mild reaction conditions.

  在乙酸中用锌加热 2-(N-芳基氨基)铬酮-3-羰基醛，可生成 2-(N-芳基氨基)-3-甲基香豆素，而 2-(N-烷基氨基)铬酮-3-羰基醛则可生成 4-羟基-3-甲基香豆素，产量适中。在非常温和的反应条件下，醛基还原成了甲基。