5-methyl-3-phenylisobenzofuran-1(3H)-one | 22297-05-8

• 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: 5-methyl-3-phenylisobenzofuran-1(3H)-one
• 英文别名: 5-methyl-3-phenyl-3H-2-benzofuran-1-one
• CAS: 22297-05-8
• 化学式: C₁₅H₁₂O₂
• 分子量: 224.259
• InChiKey: FFAAGJTZBXNWNG-UHFFFAOYSA-N

物化性质

• 沸点：
  391.8±42.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯甲酰氯 在 aluminum (III) chloride 、 氧气 作用下， 以 二甲基亚砜 为溶剂， 25.0 ℃ 、999.76 kPa 条件下， 反应 0.2h， 生成 5-methyl-3-phenylisobenzofuran-1(3H)-one
  参考文献：
  名称：

  Controlled photo-flow oxidative reaction (UV-FOR) platform for ultra-fast phthalide and API synthesis

  摘要：

  已开发出一种高效、集成且连续流的平台，用于从酮-O₂反应中合成邻苯二甲酸酯和API的实时、高通量研究。

  DOI：

  10.1039/c8gc02320d

文献信息

• Synthesis of Isoindoles by One-Electron Reductions of Dibenzo[1,4]diazocines
  作者：Marcel Bovenkerk、Birgit Esser

  DOI：10.1002/ejoc.201403315

  日期：2015.2

  A synthetic protocol to isoindoles is reported through one-electron reductions of dibenzo[1,4]diazocines. The utility of the approach has been demonstrated through the synthesis of six novel isoindole derivatives. Photophysical measurements revealed emissions between 440 and 460 nm. A reaction mechanism, supported by experimental results and quantum chemical calculations, is postulated.

  通过二苯并[1,4]重氮辛的单电子还原报告了异吲哚的合成方案。该方法的实用性已通过六种新型异吲哚衍生物的合成得到证明。光物理测量揭示了 440 和 460 nm 之间的发射。假设了由实验结果和量子化学计算支持的反应机制。
• Direct and selective synthesis of 3-arylphthalides via nickel-catalyzed aryl addition/intramolecular esterification
  作者：Qing Qiang、Feipeng Liu、Zi-Qiang Rong

  DOI：10.1016/j.tet.2021.132162

  日期：2021.6

  Herein we report a nickel-catalyzed aryl addition/intramolecular esterification in a cascade fashion. Under the combination of commercially available nickel precursor and tridentate ligand, the one pot protocol offers a direct, simple and regioselective approach to access 3-aryl phthalide derivatives from two readily available substrates with good efficiency, broad scope as well as satisfactory functional

  在此，我们以级联方式报告了镍催化的芳基加成/分子内酯化。在市售镍前体和三齿配体的组合下，一锅方案提供了一种直接、简单和区域选择性的方法，可以从两种现成的基质中获得 3-芳基苯酞衍生物，具有良好的效率、广泛的范围以及令人满意的官能团兼容性。
• Synthesis of 3‐Unsubstituted Phthalides from Aryl Amides and Paraformaldehyde via Ruthenium(II)‐Catalyzed C–H Activation
  作者：Chao Zhou、Junqi Zhao、Wenkun Chen、Mukhtar Imerhasan、Jun Wang

  DOI：10.1002/ejoc.202001160

  日期：2020.11.8

  A straightforward and convenient route has been developed for the synthesis of 3‐unsubstituted phthalide derivatives from aryl amides and paraformaldehyde by ruthenium(II)‐catalyzed C–H activation. The reaction proceeds through tandem ortho‐hydroxymethylation of aryl amide and subsequent intramolecular lactonization.

  已经开发出了一种简单易行的途径，可以通过钌（II）催化的CH活化从芳基酰胺和多聚甲醛合成3-未取代的邻苯二甲酸酯衍生物。该反应通过芳基酰胺的串联邻羟基甲基化和随后的分子内内酯化而进行。
• Carboxylate-Directed Addition of Aromatic C–H Bond to Aromatic Aldehydes under Ruthenium Catalysis
  作者：Hiroki Miura、Sachie Terajima、Tetsuya Shishido

  DOI：10.1021/acscatal.8b00680

  日期：2018.7.6

  We report that ruthenium complexes effectively catalyzed the carboxylate-directed addition of aromatic C–H bonds to aldehydes. The reactions of aromatic acids with a variety of aromatic aldehydes including unactivated ones proceeded efficiently to give the corresponding isobenzofuranone derivatives in high yields. The combination of ruthenium(II) complexes with tricyclohexylphosphine led to highly

  我们报告说，钌络合物有效催化了芳香族C–H键与醛的羧酸根定向加成。芳族酸与包括未活化的芳族醛在内的各种芳族醛的反应有效地进行，从而以高收率得到相应的异苯并呋喃酮衍生物。钌（II）配合物与三环己基膦的结合产生高度亲核的芳基金属物种，从而在没有路易斯酸的情况下实现了通用的[3 + 2]环加成反应。本文还论证了负载型钌催化剂在标题反应中的应用。
• Visible-Light-Mediated Intramolecular Lactonization of Benzylic C(sp3)–H Bonds Promoted by DDQ and tert-Butyl Nitrite
  作者：Chunmei Li、Meichao Li、Zhenlu Shen、Miaomiao Hu、Jiangyu Yang、Mengyu Niu、Meng Xu

  DOI：10.1055/a-2185-4286

  日期：——

  A functionalization of benzylic C(sp3)–H bonds was established through a mild metal-free intramolecular lactonization protocol in the presence of DDQ/tert-butyl nitrite as photocatalysts, allowing practical and low-cost access to a series of phthalide products in moderate to excellent yields. Compared with many existing methodologies, this visible-light-driven process exhibits an excellent substrate scope and fascinating features, including the formation of water as the sole byproduct, an abundant and green energy source, commercially available catalysts, and room-temperature reaction. Finally, detailed mechanistic investigations clearly revealed the role of the photocatalysts and molecular oxygen.

  摘要 在以 DDQ/亚硝酸叔丁酯为光催化剂的条件下，通过温和的无金属分子内内酯化协议建立了苄基 C(sp3)-H键的官能化，从而以中等至极好的产率获得了一系列邻苯二甲酸酯产品，而且成本低廉，非常实用。与许多现有方法相比，这种可见光驱动的工艺具有极佳的底物范围和引人入胜的特点，包括以水的形成为唯一副产物、丰富的绿色能源、市场上可买到的催化剂以及室温反应。最后，详细的机理研究清楚地揭示了光催化剂和分子氧的作用。