1-(5-phenylfuran-2-yl)-propan-2-one | 160196-21-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(5-phenylfuran-2-yl)-propan-2-one
• 英文别名: 2-Phenyl-5-acetonylfuran；2-Propanone, 1-(5-phenyl-2-furanyl)-；1-(5-phenylfuran-2-yl)propan-2-one
• CAS: 160196-21-4
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: IJGBHEPMVJSPIN-UHFFFAOYSA-N

物化性质

• 沸点：
  303.5±27.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-phenyl-1,6-dioxo-hepta-2,4-(E,E)-diene 在 氢氧化钾 作用下， 反应 6.0h， 以10%的产率得到1-(5-phenylfuran-2-yl)-propan-2-one
  参考文献：
  名称：

  Novel Cyclopentenone Synthesis by Base-Catalyzed Cyclization of Dienediones

  摘要：

  DOI：

  10.1021/jo00104a059

文献信息

• Aryl triflates: useful coupling partners for the direct arylation of heteroaryl derivatives via Pd-catalyzed C–H activation–functionalization
  作者：Julien Roger、Henri Doucet

  DOI：10.1039/b715235c

  日期：——

  Aryl triflates were found to be suitable partners for the palladium catalyzed direct arylation of heteroaromatics via C-H activation-functionalization. The reaction conditions and the catalyst have a determining influence on the yields. The system combining PPh3 and Pd(OAc)2 using KOAc as base and DMF as solvent promotes the selective 2- or 5-arylations in moderate to high yields. Several heteroaromatics

  发现芳基三氟甲磺酸酯是通过CH活化-官能化的钯催化的杂芳族化合物的直接芳基化的伙伴。反应条件和催化剂对产率具有决定性的影响。使用KOAc作为碱和DMF作为溶剂的PPh3和Pd（OAc）2组合系统可中等至高收率地促进选择性2-或5-芳基化。几种杂芳族化合物如呋喃，噻吩，噻唑或恶唑衍生物已被成功使用。芳基三氟甲磺酸酯的电子性质也对偶联产物的产率具有决定性的影响。富电子芳基三氟甲磺酸酯给出令人满意的结果，而贫电子芳基三氟甲磺酸导致苯酚的形成。
• Ong Chi Wi, Chen Chong Ming, Juang Shyh Shian, J. Org. Chem, 59 (1994) N 25, S 7915- 7916
  作者：Ong Chi Wi, Chen Chong Ming, Juang Shyh Shian

  DOI：——

  日期：——
• Dienediones as Building Blocks of an Unfused Polyaromatic Furan Ring System with Tunable Regioselectivity
  作者：Chi Wi Ong、Chong-Ming Chen、Shyh Shiaan Juang

  DOI：10.1021/jo00115a032

  日期：1995.5

  The 1,6-dioxo (E,E)-diene has two available sites for isomerization td the (Z) configuration and can undergo an intramolecular acid-catalyzed cyclization to furanonium intermediates A and B, giving two distinct regioisomeric cyclized products. With unsubstituted aryl derivatives, unfused polyaromatic furans were obtained in good yield with HCl-AcOH. Aryl groups having electron-withdrawing substituents were found to give the opposite regioselectivity. In contrast, the reaction in p-TsOH-CH2Cl2 always resulted in a mixture of regioisomeric products, irrespective of the aryl substituents. Thus, the regioselectivity in the intramolecular cyclization of 1,6-dioxo 2,4-diene can be tuned by varying the aromatic substituents and the acid conditions.