8-methyl-3,4-dihydrodibenzo[b,d]furan-1(2H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 8-methyl-3,4-dihydrodibenzo[b,d]furan-1(2H)-one
• 英文别名: 8-Methyl-3,4-dihydro-2H-dibenzofuran-1-one
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: MDLQOHHEYUTITH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  1,3-环己二酮 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 5-溴水杨醛 、 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 14.0h， 生成 8-methyl-3,4-dihydrodibenzo[b,d]furan-1(2H)-one
  参考文献：
  名称：

  Ru(II)-催化脱羰烷基化和苯甲醛与碘鎓叶立德在螯合辅助下的环化

  摘要：

  已经开发了 Ru(II) 催化的水杨醛和 2-氨基苯甲醛与碘鎓叶立德的脱羰烷基化和环化，用于合成二苯并[ b,d ]呋喃和不含 NH 的咔唑酮。该反应在温和条件下顺利进行，催化剂负载量低，底物相容性广。值得注意的是，羟基和游离氨基被证明是有效的导向基团，能够在廉价的 Ru(II) 催化剂下成功地激活醛 C-H 键以及随后的脱羰和环化。

  DOI：

  10.1021/acs.orglett.2c01843

文献信息

• Cu-Catalyzed Reaction of 1,2-Dihalobenzenes with 1,3-Cyclohexanediones for the Synthesis of 3,4-Dihydrodibenzo[<i>b,d</i>]furan-1(2<i>H</i>)-ones
  作者：Nayyef Aljaar、Chandi C. Malakar、Jürgen Conrad、Sabine Strobel、Thomas Schleid、Uwe Beifuss

  DOI：10.1021/jo3014275

  日期：2012.9.21

  The Cu(I)-catalyzed reaction of 1-bromo-2-iodobenzenes and other 1,2-dihalobenzenes with 1,3-cyclohexanediones in DMF at 130 °C using Cs2CO3 as a base and pivalic acid as an additive selectively delivers 3,4-dihydrodibenzo[b,d]furan-1(2H)-ones with yields ranging from 47 to 83%. The highly regioselective domino process is based on an intermolecular Ullmann-type C-arylation followed by an intramolecular

  在130°C下，以Cs 2 CO 3为碱，新戊酸为添加剂，在DMF中Cu（I）催化1-溴-2-碘苯和其他1,2-二卤代苯与1,3-环己二酮的反应提供3,4-dihydrodibenzo [ b，d ]呋喃-1（2 H）-one，产率为47％至83％。高度区域选择性的多米诺过程是基于分子间的Ullmann型C-芳基化，然后是分子内的Ullmann型O-芳基化。通过使用取代的1-溴-2-碘苯和取代的1,3-环己二酮作为底物，可以得到取代的产物。与无环1,3-二酮反应生成相应的苯并[ b]呋喃。
• Ir(<scp>iii</scp>)-catalyzed decarbonylative annulation of salicylaldehydes with cyclohexane-1,3-diones
  作者：Qiao-Juan Jiang、Yu-Tao Min、Yan-Ping Liu、Hua Li、Jun-Ao Peng、Cong-Jun Liu

  DOI：10.1039/d2nj05242c

  日期：——

  decarbonylative annulation of salicylaldehydes with cyclohexane-1,3-diones has been achieved via the in situ generated iodonium ylides. The reaction proceeds smoothly under mild and operationally simple conditions, affording a variety of benzofuran derivatives in moderate to high yields with good functional group tolerance. Moreover, the large-scale synthesis and further modification of the products

  通过原位生成的碘鎓叶立德，实现了 Ir( III ) 催化的水杨醛与环己烷-1,3-二酮的有效脱羰基环化反应。该反应在温和且操作简单的条件下顺利进行，以中等到高产率提供各种苯并呋喃衍生物，并具有良好的官能团耐受性。此外，产品的大规模合成和进一步修改突出了该协议的实用性。
• Reactions of a Cyclic Rhodium Carbenoid with Aromatic Compounds and Vinyl Ethers
  作者：Michael C. Pirrung、Jiancun Zhang、Karen Lackey、Daniel D. Sternbach、Frank Brown

  DOI：10.1021/jo00112a036

  日期：1995.4

  Further investigation has been made of the reactions between the cyclic diazo compound 2-diazo-1,3-cyclohexanedione and aromatic heterocycles or vinyl ethers, catalyzed by rhodium carboxylates. The extraordinary reactivity of the carbenoid derived from this diazo compound is shown by its ready reaction with solvents such as dichloromethane, dichloroethane, and fluorobenzene. Detailed investigation of its reactions with furans have shown that steric interactions dominate, both in terms of regioselectivity with unsymmetrical substrates and yield. This reaction provides a useful entry to the furo[2,3-b]furan ring system found in a number of naturally-occurring compounds and is formally a 1,3-dipolar cycloaddition. Products of net C-H insertion and with reverse regiochemistry (furo[3,2-b]furan ring system) were also detected. With pyrroles and thiophenes, cycloadducts were seen in a few cases, but were generally the exception; C-H insertion products dominate these reactions. Vinyl ethers proved reliable reactants in providing dipolar cycloadducts. The results of this study have been interpreted in terms of four pathways: an initial cyclopropanation would produce a spirocyclic dicarbonyl system that on heterolytic cleavage of one of the two cyclopropane bonds would give a zwitterion. The partitioning of such a zwitterion between ring closure and proton transfer would define the ratio of C-H insertion and dipolar cycloaddition products. Both thermodynamic and stereoelectronic arguments have been advanced to explain the observations and were supported by calculations.