3-Benzoyl-4-(1-piperidinyl)-3-cyclobutene-1,2-dione | 148875-57-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Benzoyl-4-(1-piperidinyl)-3-cyclobutene-1,2-dione
• 英文别名: 3-Benzoyl-4-piperidin-1-ylcyclobut-3-ene-1,2-dione
• CAS: 148875-57-4
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: HHZQKBNMMWFFBP-UHFFFAOYSA-N

物化性质

• 沸点：
  395.3±52.0 °C(Predicted)
• 密度：
  1.336±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Benzoyl-4-(1-piperidinyl)-3-cyclobutene-1,2-dione 在 叔丁基锂 作用下， 以 均三甲苯 为溶剂， 反应 12.17h， 生成 4-acetoxy-3-benzoyl-1-(4-(N,N-dimethylamino)phenyl)-2-(1-piperidinyl)furan
  参考文献：
  名称：

  Construction of Highly-Substituted Aromatics Bearing Acyl Substituents Using Cyclobutenedione Technology: Vinylketene-Based Benzannulations Using 3-Acyl-4-(substituted amino)cyclobutenediones

  摘要：

  Highly-substituted acylated aromatics were efficiently synthesized from 3-acylcyclobutenediones via vinylketene-based benzannulations. Aryl and alkenyl lithiates added regioselectively to 3-acyl-4-(substituted amino)-3-cyclobutene-1,2-diones at -78 degrees C to produce the corresponding 4-aryl- and 4-alkenyl-3-(substituted amino)-2-acylcyclobutenones in good yields. Substrates lacking the vinylogous amide functionality were not preparable by this route, because the acylcyclobutenedione starting materials are not sufficiently stable to manipulate. Benzannulations of 4-(3-furyl)-, 4-(2-thienyl)-, 4-(2-dihydropyranyl)-, 4-(2-dihydrofuranyl)-, 4-(1-naphthyl)-, and 4-(2-naphthyl)substituted cyclobutenones proceeded in refluxing mesitylene to give the corresponding acyl aromatics in 80-90% yield. Of all the 4-arylcyclobutenones synthesized (aryl = phenyl and substituted phenyl), only those with an electron-donating substituent (OMe, NMe(2)) at the meta position of phenyl group underwent benzannulation in refluxing mesitylene to afford acyl aromatics in moderate yields.

  DOI：

  10.1021/jo00130a018
• 作为产物：
  描述：

  苯甲酰氯 、 3-(1-Piperidinyl)-4-(tri-n-butylstannyl)-3-cyclobutene-1,2-dione 在 copper(l) iodide 、 benzoylchlorobis(triphenylphosphine)palladium(II) 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以92%的产率得到3-Benzoyl-4-(1-piperidinyl)-3-cyclobutene-1,2-dione
  参考文献：
  名称：

  Preparation of 3-acyl-3-cyclobutene-1,2-diones and some related monoacetals

  摘要：

  3-(Tri-n-butylstannyl)-3-cyclobutene-1,2-diones and 4-methyl-3-(tri-n-butylstannyl)-3-cyclobutene-1,2-dione 2-ethylene acetal participate in palladium/copper-cocatalyzed cross-coupling with acyl halides and in palladium-catalyzed carbonylative cross-coupling with aryl/heteroaryl iodides. The derived 3-acyl-3-cyclobutenediones and cyclobutenedione monoacetals should extend the potential of cyclobutenedione-based synthetic organic methodology.

  DOI：

  10.1021/jo00065a016