| 1320362-85-3

• 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
• CAS: 1320362-85-3
• 化学式: C₁₇H₁₁NO₂S
• 分子量: 293.346
• InChiKey: OOWLLYMJKJLSJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  39.19
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  在 trans-bis(triphenylphosphine)palladium dichloride 、 碘 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 3-(1,8-dimethoxy-3-thiophen-3-yl-1H-pyrano[4,3-b]quinolin-4-yl)prop-2-enenitrile
  参考文献：
  名称：

  Pyrano[4,3-b]quinolines Library Generation via Iodocyclization and Palladium-Catalyzed Coupling Reactions

  摘要：

  Synthesis of a 80-member library of novel pyrano[4,3-b]quinoline in solution-Phase is reported. The key intermediate, 4-iodopyrano[4,3-b]quinolines were synthesized by the electropHic iodocyclization of corresponding oho-alkynyl ' aldehydes in good to excellent yields under mild reaction,conditions. Subsequently a diverse set of libraries was generated by employing palladium:catalyzed Suzuki-Miyauta, Heck, and Sonogashira coupling reactions on 4-iodopyrano[4,3-b]quinolines. In this:way,- a series of structurally different and biologically interesting molecules were obtained. Some of the selected compounds were screened against 3D7 strains of Plasmodium falciparum for antimalarial activity. Suzuki coupling products 6{3} and 6{21} and Heck coupling product 8{12} exhibit promising antimalarial activity.

  DOI：

  10.1021/co200100z
• 作为产物：
  描述：

  3-乙炔基噻吩 、 2-氯-6-甲氧基喹啉-3-甲醛 在 trans-bis(triphenylphosphine)palladium dichloride 、 三乙胺 作用下， 生成
  参考文献：
  名称：

  Pyrano[4,3-b]quinolines Library Generation via Iodocyclization and Palladium-Catalyzed Coupling Reactions

  摘要：

  Synthesis of a 80-member library of novel pyrano[4,3-b]quinoline in solution-Phase is reported. The key intermediate, 4-iodopyrano[4,3-b]quinolines were synthesized by the electropHic iodocyclization of corresponding oho-alkynyl ' aldehydes in good to excellent yields under mild reaction,conditions. Subsequently a diverse set of libraries was generated by employing palladium:catalyzed Suzuki-Miyauta, Heck, and Sonogashira coupling reactions on 4-iodopyrano[4,3-b]quinolines. In this:way,- a series of structurally different and biologically interesting molecules were obtained. Some of the selected compounds were screened against 3D7 strains of Plasmodium falciparum for antimalarial activity. Suzuki coupling products 6{3} and 6{21} and Heck coupling product 8{12} exhibit promising antimalarial activity.

  DOI：

  10.1021/co200100z

文献信息

• Azidation vs [3 + 2]-cycloaddition: Chemoselective reaction of sodium azide towards o-alkynylaldehydes for the synthesis of N-heterocycles
  作者：Pradeep Kumar、Vineeta Garg、Akhilesh K. Verma

  DOI：10.1016/j.tetlet.2019.06.022

  日期：2019.7

  The chemoselective synthesis of functionalized azido- and triazolo-containing nitrogen heterocycles using sodium azide and o-alkynylaldehydes has been described. The azidation reaction was preferred in acetonitrile while the [3 + 2]-cycloaddition was favored in DMSO. Furthermore, the azido-pyranoquinolines were employed for the synthesis of benzonaphthyridines via the Staudinger reaction at room temperature

  已经描述了使用叠氮化钠和邻炔基醛化学合成官能化的含叠氮基和三唑基的氮杂环。在乙腈中优选叠氮化反应，而在DMSO中偏向[3 + 2]-环加成反应。此外，在室温下，通过Staudinger反应，将叠氮基-吡喃喹啉用于苯并萘并吡啶类化合物的合成。
• Chemoselective Azidation of <i>o</i>-Alkynylaldehydes over [3 + 2] Cycloaddition and Subsequent Staudinger Reaction: Access to Benzonaphthyridines/Naphthyridines
  作者：Pradeep Kumar、Trapti Aggarwal、Akhilesh K. Verma

  DOI：10.1021/acs.joc.7b01016

  日期：2017.6.16

  conditions is described. Mechanistic studies confirm the formation of azido-pyranoquinolines through nucleophilic attack of azide on pyrilium intermediate over [3 + 2] cycloaddition of the azide on the alkyne. The synthesized azido-pyranoquinolines were transformed into benzonaphthyridines via Staudinger reaction. The mechanistic pathway was supported by deuterium labeling experiment and X-ray crystallographic

  描述了一种在温和的反应条件下，在叠氮化钠存在下，通过邻炔基醛的亲电环化化学合成功能化的叠氮基-吡喃喹啉和叠氮基-碘吡喃并喹啉的有效串联方法。机理研究证实，叠氮化物在炔烃上的[3 + 2]环加成反应中，叠氮化物对pyr中间体的亲核攻击可形成叠氮基-吡喃喹啉。通过Staudinger反应将合成的叠氮基-吡喃喹啉转化为苯并萘啶。氘标记实验和X射线晶体学研究为该机理提供了支持。
• Unveiling the Three-Component Phosphonylation on Alkynylaldehydes: Toolbox toward Fluorescent Molecules
  作者：Deepika Thakur、Trapti Aggarwal、Muskan、Sushmita、Akhilesh K. Verma

  DOI：10.1021/acs.joc.2c02915

  日期：2023.2.17

  A regioselective tandem approach for annulated napthyridines/isoquinolines embedded with the phosphine oxide group under mild reaction conditions has been achieved in good to excellent yields. The designed strategy involves the triflate-induced formation of new C sp3–P and C sp2–N bond formation in one pot. This protocol was also well tolerated for the construction of densely functionalized organo-phosphorylated

  在温和的反应条件下，已经实现了一种区域选择性串联方法，用于嵌入氧化膦基团的环状萘啶/异喹啉，收率良好。设计的策略涉及三氟甲磺酸诱导在一个锅中形成新的 C sp 3 -P 和 C sp 2 -N 键。该协议对于以良好的产量构建密集功能化的有机磷酸化色烯也具有很好的耐受性。此外，膦衍生的磺胺二甲嘧啶和磺胺甲恶唑药物也以良好的收率成功合成。机理研究表明，离子通路和区域选择性6-内切酶的形成通过 X 射线晶体学研究证实了环化产物。有趣的是，选择性化合物的光物理研究揭示了它们的激发荧光特性。
• Harnessing the Reactivity of ortho-Alkynylaldehydes: Silver Triflate Catalyzed Regioselective Synthesis of Phosphonylated Fluorescent Molecules
  作者：Deepika Thakur、Shivam A. Meena、Akhilesh K. Verma、Sushmita Sushmita

  DOI：10.1055/a-2356-8347

  日期：2025.1

  An efficient approach for the facile synthesis of phosphonylated 1,3-dihydrofuro[3,4-b]quinolines and dihydrofuro[3,4-b]pyridines is developed. Reaction proceeds by the formation of new C–P and C–O bonds affording Z-selective phosphonylated products at room temperature. Diphenylphosphine oxides and dialkyl phosphites are explicitly incorporated into the carbonyl carbon of o-alkynylaldehydes in good

  开发了一种轻松合成膦酰化1,3-二氢呋喃并[3,4-b]喹啉和二氢呋喃并[3,4-b]吡啶的有效方法。反应通过形成新的 C-P 和 C-O 键进行，在室温下提供 Z-选择性膦酰化产物。二苯基氧化膦和亚磷酸二烷基酯以良好至优异的产率明确地结合到邻炔醛的羰基碳中。该反应条件温和，底物范围广泛，并在银催化剂存在下形成三个新键。机理研究表明，反应通过离子途径以 5-exo-dig 方式进行，产生 Z 选择性产物，并通过 X 射线晶体学研究得到验证。对所选化合物的光物理研究揭示了 455 nm 范围内的发射最大值。