5-bromo-4,6-dimethylbenzofuran-2,3-dione | 1453085-66-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: 5-bromo-4,6-dimethylbenzofuran-2,3-dione
• 英文别名: 5-Bromo-4,6-dimethyl-1-benzofuran-2,3-dione
• CAS: 1453085-66-9
• 化学式: C₁₀H₇BrO₃
• 分子量: 255.068
• InChiKey: SENVFZHHQPRKCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-4,6-dimethylbenzofuran-2,3-dione 、 苯硼酸 在 (R)-Me-BIPAM 、 potassium fluoride 、 tris(triphenylphosphine)ruthenium(II) chloride 、 乙腈 作用下， 以 水 、 甲苯 为溶剂， 反应 18.0h， 以80%的产率得到(3S)-5-bromo-3-hydroxy-4,6-dimethyl-3-phenyl-2,3-dihydro-1-benzofuran-2-one
  参考文献：
  名称：

  Ruthenium–Me-BIPAM-catalyzed addition reaction of aryl-boronic acids to benzofuran-2,3-diones for the enantioselective synthesis of 3-aryl-3-hydroxybenzofuran-2-ones

  摘要：

  We have developed an enantioselective synthesis of 3-aryl-3-hydroxybenzofuran-2-ones via the ruthenium-catalyzed 1,2-addition of arylboronic acids to benzofuran-2,3-diones. The use of RuCl2(PPh3)(3) with a chiral bidentate phosphoramidite ligand [(R,R)-Me-BIPAM] in the presence of a small amount of acetonitrile (20 mol %) gave optically active 3-aryl-3-hydroxybenzofuran-2-ones with up to 96% ee. This reaction is the first example of a catalytic asymmetric 1,2-addition reaction of arylboronic acids to benzofuran-2,3-diones for the highly efficient and enantioselective synthesis of quaternary carbon containing benzofuran-2-ones. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.10.010
• 作为产物：
  描述：

  草酰氯 、 4-溴-3,5-二甲酚 在 4-二甲氨基吡啶 、 aluminum (III) chloride 、 水 作用下， 以 氯仿 、 1,2-二氯乙烷 为溶剂， 反应 20.0h， 生成 5-bromo-4,6-dimethylbenzofuran-2,3-dione
  参考文献：
  名称：

  Ruthenium–Me-BIPAM-catalyzed addition reaction of aryl-boronic acids to benzofuran-2,3-diones for the enantioselective synthesis of 3-aryl-3-hydroxybenzofuran-2-ones

  摘要：

  We have developed an enantioselective synthesis of 3-aryl-3-hydroxybenzofuran-2-ones via the ruthenium-catalyzed 1,2-addition of arylboronic acids to benzofuran-2,3-diones. The use of RuCl2(PPh3)(3) with a chiral bidentate phosphoramidite ligand [(R,R)-Me-BIPAM] in the presence of a small amount of acetonitrile (20 mol %) gave optically active 3-aryl-3-hydroxybenzofuran-2-ones with up to 96% ee. This reaction is the first example of a catalytic asymmetric 1,2-addition reaction of arylboronic acids to benzofuran-2,3-diones for the highly efficient and enantioselective synthesis of quaternary carbon containing benzofuran-2-ones. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.10.010

文献信息

• A novel reaction of the ‘Huisgen zwitterion’ with benzofuran-2,3-diones: an efficient strategy for the synthesis of spirocyclic benzofuran-2-one derivatives
  作者：Ze-Dong Wang、Nan Dong、Feng Wang、Xin Li、Jin-Pei Cheng

  DOI：10.1016/j.tetlet.2013.07.129

  日期：2013.10

  nitrogen-based nucleophile generated from azodicarboxylate and triphenylphosphine displayed good reactivity toward benzofuran-2,3-diones to generate a variety of spirocyclic benzofuran-2-one derivatives. The reactions accommodate a number of benzofuran-2,3-diones and different dialkylazodicarboxylates to give the enriched functionalized 3-spirooxadiazole benzofuran-2-ones with moderate to good yields (up

  由偶氮二羧酸盐和三苯基膦生成的氮基亲核试剂对苯并呋喃-2,3-二酮显示出良好的反应活性，可生成多种螺环苯并呋喃-2-酮衍生物。该反应容纳许多苯并呋喃-2，3-二酮和不同的二烷基偶氮二羧酸酯，以中等至良好的产率（高达93％）得到富集的官能化的3-螺并恶二唑苯并呋喃-2-酮。