4-(p-tolyl)-2,3-dihydrofuro[3,2-c]quinoline | 1027224-39-0

• 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: 4-(p-tolyl)-2,3-dihydrofuro[3,2-c]quinoline
• 英文别名: 4-(4-Methylphenyl)-2,3-dihydrofuro[3,2-c]quinoline；4-(4-methylphenyl)-2,3-dihydrofuro[3,2-c]quinoline
• CAS: 1027224-39-0
• 化学式: C₁₈H₁₅NO
• 分子量: 261.323
• InChiKey: RSHAFRBEFZIMDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(4-methylbenzylidene)-2-iodoaniline 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 碘 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.0h， 生成 4-(p-tolyl)-2,3-dihydrofuro[3,2-c]quinoline
  参考文献：
  名称：

  Scaffold-Divergent Synthesis of Ring-Fused Indoles, Quinolines, and Quinolones via Iodonium-Induced Reaction Cascades

  摘要：

  N-(2-lodophenyl)imines A are readily formed from Schiff's base condensation of 2-iodoanilines with carbonyls and ketals. These imines provide useful substrates in scaffold-divergent synthesis through the attachment of an alkyne (Songashira coupling or acyl substitution of a Weinreb amide) followed by an iodonium-induced reaction cascade to give ring-fused indoles B, quinolines C, or quinolones D depending on the reaction conditions employed.

  DOI：

  10.1021/jo400125p

文献信息

• Silver-catalyzed tandem 5- and 6-<i>endo</i>-cyclizations <i>via</i> concomitant yne-ol-imine activation: selective entry to 2-aryldihydrofuroquinolines
  作者：Swastik Karmakar、Prasanta Das、Sandip Kundu

  DOI：10.1039/d1nj02643g

  日期：——

  Ag(i)-catalyzed domino imination-intramolecular bi-heterocyclization-aromatization cascade has been developed to construct 2-aryldihydrofuroquinolines from aldehyde and unprotected 4-(2-aminophenyl)but-3-yn-1-ol via tandem 5-endo-dig and 6-endo-trig cyclization.

  已开发出Ag（i）催化的多米诺亚胺化-分子内双杂环化-芳构化级联反应，用于从醛和未保护的4-(2-氨基苯基)丁-3-炔-1-醇构建2-芳基二氢呋喃喹啉，通过串联5-内端挖和6-内端挖环化。
• Acid‐Mediated Condensation of 2‐Aminoaryl Cyclopropyl Ketones with Aldehydes for the Synthesis of 2,3‐Dihydrofuro[3,2‐c]quinolines
  作者：Wenbo Cai、Cong Zhang、Xin Wang、Chuanjun Song

  DOI：10.1002/adsc.202400263

  日期：——

  A method for the synthesis of 2,3-dihydrofuro[3,2-c]quinolines via TfOH or TMSOTf mediated condensation of 2-aminoaryl cyclopropyl ketones with aldehydes has been developed. The reaction proceeds under transition metal or halogen free conditions, giving access to the target molecules in 27-90% isolated yields. Mechanistic study indicates that the reaction sequence involves imine formation, intramolecular

  开发了一种通过 TfOH 或 TMSOTf 介导的 2-氨基芳基环丙基酮与醛的缩合合成 2,3-二氢呋喃并[3,2-c]喹啉的方法。该反应在无过渡金属或卤素的条件下进行，以 27-90% 的分离产率获得目标分子。机理研究表明，反应顺序涉及亚胺形成、分子内曼尼希缩合、Cloke-Wilson 重排和自动氧化。
• Alternating Iodonium-Mediated Reaction Cascades Giving Indole- And Quinoline-Containing Polycycles
  作者：Rosliana Halim、Peter J. Scammells、Bernard L. Flynn

  DOI：10.1021/ol800202u

  日期：2008.5.1

  A simple two-step convergent protocol gives direct access to synthetic intermediate A from ortho-iodoanilines. Intermediate A can be treated with NIS in CH(2)Cl(2) to induce novel iodonium mediated domino reaction cascade, which provides direct access to ring-fused indole compounds B. Simply by changing the reaction conditions, this protocol can be directed down an alternative domino reaction cascade to give various ring fused quinoline compounds C.
• Synergistic Effect of Pd(II) and Acid Catalysts on Tandem Annulation Reaction for the Regioselective Synthesis of Ring-Fused Quinolines
  作者：Su-Kyung Ock、So-Won Youn

  DOI：10.5012/bkcs.2010.31.03.704

  日期：2010.3.20
• Scaffold-Divergent Synthesis of Ring-Fused Indoles, Quinolines, and Quinolones via Iodonium-Induced Reaction Cascades
  作者：Rosliana Halim、Luigi Aurelio、Peter J. Scammells、Bernard L. Flynn

  DOI：10.1021/jo400125p

  日期：2013.5.17

  N-(2-lodophenyl)imines A are readily formed from Schiff's base condensation of 2-iodoanilines with carbonyls and ketals. These imines provide useful substrates in scaffold-divergent synthesis through the attachment of an alkyne (Songashira coupling or acyl substitution of a Weinreb amide) followed by an iodonium-induced reaction cascade to give ring-fused indoles B, quinolines C, or quinolones D depending on the reaction conditions employed.