4,6,7-trimethylbenzofuran-2,3-dione | 31297-33-3

• 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: 4,6,7-trimethylbenzofuran-2,3-dione
• 英文别名: 4,6,7-trimethyl-benzofuran-2,3-dione；4,6,7-Trimethyl-benzofuran-2,3-dion；4,6,7-Trimethylcoumaran-2,3-dion；2,3-Dihydro-4,6,7-trimethyl-2,3-dioxobenzofuran；4,6,7-trimethyl-1-benzofuran-2,3-dione
• CAS: 31297-33-3
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: JHBPNVCMWVCRNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  4,6,7-trimethylbenzofuran-2,3-dione 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 Hydroxy-(2-hydroxy-3,4,6-trimethyl-phenyl)-acetic acid
  参考文献：
  名称：

  Steric Effects of Alkyl Substituents upon the Opening of the Lactone Ring of Coumaran-2,3-diones

  摘要：

  烷基取代的香豆素-2,3-二酮的内酯环对水解和醇解的稳定性在很大程度上受到烷基取代基位置的影响。紫外光谱研究表明，由于立体原因，内酯环邻近位置的甲基取代有助于提高稳定性。

  DOI：

  10.1246/bcsj.43.3891
• 作为产物：
  描述：

  1,4-bis-(2-hydroxy-3,4,6-trimethyl-phenyl)-butane-1,4-dione 在 吡啶 、 碘 作用下， 生成 4,6,7-trimethylbenzofuran-2,3-dione
  参考文献：
  名称：

  Action of Pyridine and Iodine upon Two o-Phenolic-1,4-diketones: 4,6,7-Trimethylcoumarandione and its 5-Hydroxy Derivative

  摘要：

  DOI：

  10.1021/ja01153a078

文献信息

• An efficient diastereoselective synthesis of spiro pyrido[2,1-b][1,3]oxazines via a novel pyridine-based three-component reaction
  作者：Abbas Ali Esmaeili、Hamid Vesalipoor、Rahele Hosseinabadi、Alireza Fakhari Zavareh、Mohammad Ali Naseri、Ebrahim Ghiamati

  DOI：10.1016/j.tetlet.2011.07.039

  日期：2011.9

  The zwitterions generated from pyridine and dialkyl acetylenedicarboxylate (DAAD) reacted with benzofuran-2,3-diones to form highly substituted spiro pyrido[2,1-b][1,3]oxazines in good to high yields without using a catalyst.

  由吡啶和乙酰二羧酸二烷基酯（DAAD）生成的两性离子与苯并呋喃-2,3-二酮反应形成高取代的螺吡啶并[2,1- b ] [1,3]恶嗪，而无需使用催化剂。
• 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。
• N-heterocyclic carbene catalyzed annulation of benzofuran-2,3-diones and enals: a concise synthesis of spiro-bis-lactone
  作者：Ze-Dong Wang、Feng Wang、Xin Li、Jin-Pei Cheng

  DOI：10.1039/c3ob41028e

  日期：——

  The N-heterocyclic carbene catalyzed annulation of benzofuran-2,3-diones and enals via homoenolate intermediates is described. The reaction provided a direct and efficient method for the synthesis of spiro-bis-lactones. The ketone-carbonyl group annulated products and the ester-carbonyl group annulated products can be obtained as major products with good yields by convenient catalyst regulation. Furthermore

  描述了N-杂环卡宾经由均烯酸酯中间体催化苯并呋喃-2,3-二酮和烯醛的环化。该反应提供了合成螺双-双内酯的直接有效的方法。通过方便的催化剂调节，酮-羰基环化产物和酯-羰基环化产物可以良好的收率得到为主要产物。此外，可商购的噻唑鎓盐也可以中等收率催化该反应。
• Reaction of Isocyanides, Dialkyl Acetylenedicarboxylates, and α-Keto Lactones: Unexpected Participation of an Ester Carbonyl Group in the Isocyanide-Based Three-Component Reaction
  作者：Abbas Esmaeili、Hamid Vesalipoor

  DOI：10.1055/s-0028-1088042

  日期：2009.5

  The reaction of benzofuran-2,3-dione derivatives with dialkyl acetylenedicarboxylates and alkyl isocyanides results in a three-component addition reaction in which the ester carbonyl group is incorporated into a two-atom assembling unit to give highly functionalized γ-spiroiminolactones in good yield. This reaction provides the first example of an ester carbonyl group participating in an isocyanide-based

  苯并呋喃-2,3-二酮衍生物与乙炔二羧酸二烷基酯和烷基异氰化物的反应导致三组分加成反应，其中酯羰基被掺入到两个原子的组装单元中，从而以高收率获得高度官能化的γ-螺氨基内酯。该反应提供了参与基于异氰化物的多组分反应的酯羰基的第一个例子。 酮-炔二羧酸二烷基酯-烷基异氰化物-螺化合物-内酯
• One-Pot, Three-Component Chemoselective Reaction of Isoquinolines, Dialkyl Acetylenedicarboxylates, and α-Ketolactones: An Unexpected Participation of an Ester Carbonyl Group in the 1,4-Dipolar Cycloaddition Reaction
  作者：Abbas Esmaeili、Mohsen Nazer

  DOI：10.1055/s-0029-1217705

  日期：2009.8

  The reaction of benzofuran-2,3-dione derivatives with dialkyl acetylenedicarboxylates (DAAD) and isoquinoline results in a three-component 1,4-dipolar cycloaddition reaction in which the ester carbonyl group is incorporated into a two-atom assembly to give spiro[1,3]oxazino[2,3-α]isoquinoline derivatives in good yield. This reaction provides the first example of an ester carbonyl group participating

  苯并呋喃-2,3-二酮衍生物与乙炔二羧酸二烷基酯 (DAAD) 和异喹啉的反应产生三组分 1,4-偶极环加成反应，其中酯羰基结合到一个双原子组装体中，得到螺[ 1,3]恶嗪并[2,3-α]异喹啉衍生物，收率良好。该反应提供了酯羰基参与 1,4-偶极环加成反应的第一个例子。

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