ethyl 4-(4-methylbenzoyl)-2-phenyl-5-p-tolylfuran-3-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: ethyl 4-(4-methylbenzoyl)-2-phenyl-5-p-tolylfuran-3-carboxylate
• 英文别名: Ethyl 4-(4-methylbenzoyl)-5-(4-methylphenyl)-2-phenylfuran-3-carboxylate；ethyl 4-(4-methylbenzoyl)-5-(4-methylphenyl)-2-phenylfuran-3-carboxylate
• 化学式: C₂₈H₂₄O₄
• 分子量: 424.496
• InChiKey: BHMLGCHUQQMBBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-二(4-甲基苯基)丙烷-1,3-二酮 、 (1Z)-2-偶氮基-1-乙氧基-3-氧代-3-苯基-1-丙烯-1-醇 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以72%的产率得到ethyl 4-(4-methylbenzoyl)-2-phenyl-5-p-tolylfuran-3-carboxylate
  参考文献：
  名称：

  Piano-Stool Rhodium Enalcarbenoids: Application to Catalyst-Controlled Metal-Templated Annulations of Diazoenals and 1,3-Dicarbonyls

  摘要：

  An electrophilic piano-stool rhodium(III)-enalcarbenoid resulted from the reaction of diazoenal with the cationic Cp*Rh-III in the presence of a 1,3-diketone. The synthetic utility of these transient carbenoids has been demonstrated in the metal-templated [3 + 2] annulation of diazoenals and 1,3-dicarbonyls, thus leading to the enal-functionalized tetrasubstituted furans. The significance of the piano-stool enalcarbenoids has been further exemplified by the mechanistically distinct, complementary Lewis acid templated [2 + 3] annulation of diazoenals and 1,3-dicarbonyls, resulting in the trisubstituted furanyl-enones and acrylates. Mechanistic investigations revealed that these annulations proceed through catalyst-dependent chemoselective activation of diazoenal by the in situ formed metal diketonates. These methodologies gave access to core structures of indeno[1,2-b]furans, tetracyclic OLED, and a pan-AKT inhibitor.

  DOI：

  10.1021/acscatal.8b03865

文献信息

• Phosphane-Mediated Domino Synthesis of Tetrasubstituted Furans from Simple Terminal Activated Olefins
  作者：Jianfang Wang、Rong Zhou、Zheng-Rong He、Zhengjie He

  DOI：10.1002/ejoc.201200945

  日期：2012.10

  Convenient and highly efficient syntheses of tetrasubstituted furans with flexible substituent patterns from simple and readily available starting materials have been developed. Under very mild conditions, with the mediation of stoichiometric nBu3P, simple terminal activated olefins and acyl chlorides or anhydrides smoothly furnish tetrasubstituted furans in modest to excellent yields. This synthetic

  已经开发了从简单且容易获得的起始材料中方便且高效地合成具有灵活取代模式的四取代呋喃。在非常温和的条件下，在化学计量的 nBu3P 的介导下，简单的末端活化烯烃和酰氯或酸酐以中等至极好的收率平稳地提供四取代呋喃。这种合成策略具有灵活选择取代基模式和 C-酰化/O-酰化/C-酰化/分子内 Wittig 反应多重多米诺组装序列的特点。
• Convergent Synthesis of Polysubstituted Furans via Catalytic Phosphine Mediated Multicomponent Reactions
  作者：Xia Fan、Rongshun Chen、Jie Han、Zhengjie He

  DOI：10.3390/molecules24244595

  日期：——

  Tri- or tetrasubstituted furans have been prepared from terminal activated olefins and acyl chlorides or anhydrides by a multicomponental convergent synthesis mode. Instead of stoichiometric nBu3P, only catalytic nBu3P or nBu3P=O is needed to furnish the furans in modest to excellent yields with a good functional group tolerance under the aid of reducing agent silane. This synthetic method features

  三或四取代的呋喃已通过多组分聚合合成模式由末端活化的烯烃和酰氯或酸酐制备。代替化学计量的 nBu3P，只需要催化 nBu3P 或 nBu3P=O 即可在还原剂硅烷的帮助下以中等至极好的收率提供具有良好官能团耐受性的呋喃。该合成方法以硅烷驱动的催化分子内 Wittig 反应为关键环化步骤，代表了催化 Wittig 反应在多组分级联反应中的首次成功应用。