1-(4-benzoyl-2-methyl-5-phenylfuran-3-yl)ethanone | 58329-48-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-benzoyl-2-methyl-5-phenylfuran-3-yl)ethanone
• 英文别名: 1-(4-benzoyl-2-methyl-5-phenylfuran-3-yl)ethan-1-one
• CAS: 58329-48-9
• 化学式: C₂₀H₁₆O₃
• 分子量: 304.345
• InChiKey: BUTBUGKUHJGTAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  47.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-benzoyl-2-methyl-5-phenylfuran-3-yl)ethanone 、 肼 生成 1,7-dimethyl-4,5-diphenylpyrrolo[3,4-d]pyridazin-6-amine
  参考文献：
  名称：

  EICHER T.; SCHAEFER V., TETRAHEDRON LETT. , 1975, NO 45, 3919-3922

  摘要：

  DOI：
• 作为产物：
  描述：

  (2Z)-3-偶氮基-4-氧代-2-戊烯-2-醇 、 二苯甲酰基甲烷 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.0h， 以87%的产率得到1-(4-benzoyl-2-methyl-5-phenylfuran-3-yl)ethanone
  参考文献：
  名称：

  Rh(III)-催化的 2-重氮-1,3-二酮与 1,3-二羰基化合物的级联亲核加成/环化以获得 6,7-二氢苯并呋喃-4(5 H )-酮

  摘要：

  2-重氮-1,3-二酮与1,3-二羰基化合物（例如1,3-二酮和β-酮​​酯）的Rh(III)催化级联亲核加成/分子内环化得到6, 7-dihydrobenzofuran-4(5 H )-ones 的产率高达 91%。值得注意的是，在优化的反应条件下，广泛的底物和官能团具有良好的耐受性，以中等至优异的产率得到所需产物，同时释放出 N 2和 H 2 O 作为副产物。此外，所描述的方法是可扩展的，适用于后期功能化。

  DOI：

  10.1021/acs.joc.1c00259

文献信息

• Direct CuO nanoparticle-catalyzed synthesis of poly-substituted furans via oxidative C–H/C–H functionalization in aqueous medium
  作者：Soumen Payra、Arijit Saha、Sandip Guchhait、Subhash Banerjee

  DOI：10.1039/c6ra04181g

  日期：——

  Here, we have reported synthesis of 3,4-dicarbonyl substituted poly-functionalized furan derivatives via direct functionalization of α,β-unsaturated carbonyl compounds through conjugate addition initiated domino reactions using CuO nanoparticles as a reusable catalyst in aqueous ethanol.

  在这里，我们已经报道3,4-二羰基取代的聚官能呋喃衍生物的合成通过α的直接官能化，通过共轭加成β不饱和羰基化合物起始使用的CuO纳米颗粒作为含水乙醇中可重复使用的催化剂多米诺反应。
• Photocatalytic synthesis of tetra-substituted furans promoted by carbon dioxide
  作者：Ya-Ming Tian、Huaiju Wang、Ritu、Burkhard König

  DOI：10.1039/d1sc06403g

  日期：——

  compounds in carbon dioxide (CO2) atmosphere under mild conditions. It was found that CO2 could be incorporated at the diketone enolic OH position, which was key to enabling the cleavage of a C–O bond during the rearrangement of a cyclopropane intermediate. This method allows for the same-pot construction of two isomers of the high-value tetra-substituted furan scaffold. The synthetic scope and preliminary

  我们报告了一个简单的协议，用于在温和条件下在二氧化碳 (CO 2 ) 气氛中将 1,3-二酮转化为无过渡金属、可见光驱动的四取代呋喃骨架化合物。发现CO 2可以掺入二酮烯醇OH位置，这是在环丙烷中间体重排期间能够裂解C-O键的关键。该方法允许高价值四取代呋喃支架的两种异构体的同一罐构造。介绍了合成范围和初步机理研究。
• Piano-Stool Rhodium Enalcarbenoids: Application to Catalyst-Controlled Metal-Templated Annulations of Diazoenals and 1,3-Dicarbonyls
  作者：Bapurao Sudam Lad、Sreenivas Katukojvala

  DOI：10.1021/acscatal.8b03865

  日期：2018.12.7

  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.
• Manganese Dioxide-Mediated Oxidative Coupling of 1,3-Dicarbonyl Compounds with α,β-Unsaturated Ketones: Direct Access to 3,4-Dicarbonyl Substituted Furans
  作者：Yuanyuan Yue、Yuanli Zhang、Weiwei Song、Xin Zhang、Jianming Liu、Kelei Zhuo

  DOI：10.1002/adsc.201400097

  日期：2014.8.11

  AbstractAn efficient manganese dioxide‐mediated and highly selective oxidative CH/CH functionalization of 1,3‐dicarbonyl compounds with α,β‐unsaturated ketones for the construction of tetrasubstituted furans in one step has been demonstrated. This catalytic system converts two CH bonds and CO bonds to CC and CO bonds. This reaction provides a facile and regio‐defined method for the synthesis of 3,4‐dicarbonyl substituted furans.magnified image