3-(3-甲基苯基)-3H-2-苯并呋喃-1-酮 | 90445-45-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 3-(3-甲基苯基)-3H-2-苯并呋喃-1-酮
• 英文名称: 3-(m-tolyl)isobenzofuran-1(3H)-one
• 英文别名: 3-m-tolylisobenzofuran-1(3H)-one；3-m-tolyl-phthalide；3-m-Tolyl-phthalid；3-(3-Methylphenyl)-2-benzofuran-1(3H)-one；3-(3-methylphenyl)-3H-2-benzofuran-1-one
• CAS: 90445-45-7
• 化学式: C₁₅H₁₂O₂
• 分子量: 224.259
• InChiKey: XCTUXIMLWKXQJC-UHFFFAOYSA-N

物化性质

• 熔点：
  86.6 °C
• 沸点：
  381.1±41.0 °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：

  2-m-Toluoyl-benzil 在 氢氧化钾 作用下， 生成 3-(3-甲基苯基)-3H-2-苯并呋喃-1-酮
  参考文献：
  名称：

  Dalew, Godisnik na Sofijskia universitet. Himiceski fakultet., 41 Chimija <1944/45> 37, 52

  摘要：

  DOI：

文献信息

• Scalable Electrochemical Dehydrogenative Lactonization of C(sp²/sp³)–H Bonds
  作者：Sheng Zhang、Lijun Li、Huiqiao Wang、Qian Li、Wenmin Liu、Kun Xu、Chengchu Zeng

  DOI：10.1021/acs.orglett.7b03617

  日期：2018.1.5

  A practical, electrochemical method is developed for the direct dehydrogenative lactonization of C(sp2/sp3)–H bonds under external oxidant- and metal-free conditions, delivering diverse lactones, including coumarin derivatives with excellent regioselectivity. The scalable nature of this newly developed electrochemical process was demonstrated on a 40 g scale following an operationally simple protocol

  开发了一种实用的电化学方法，用于在无外部氧化剂和无金属的条件下对C（sp 2 / sp 3）–H键进行直接脱氢内酯化，从而提供多种内酯，包括具有优异区域选择性的香豆素衍生物。遵循操作简单的协议，以40 g规模展示了这种新开发的电化学过程的可扩展性。C（sp 3）-H键的远程内酯化将构成朝着电化学C-O键形成的重要合成进展。
• Rhenium-Catalyzed Phthalide Synthesis from Benzamides and Aldehydes via C–H Bond Activation
  作者：Bing Jia、Yunhui Yang、Xiqing Jin、Guoliang Mao、Congyang Wang

  DOI：10.1021/acs.orglett.9b02142

  日期：2019.8.16

  The [4 + 1] annulation of benzamides and aldehydes for phthalide synthesis was achieved via rhenium-catalyzed C–H activation, which demonstrates an unprecedented reaction pattern distinct from those of other transition-metal catalyses. The reaction also features readily available starting materials, a wide scope for both electro-rich and electro-deficient substrates, and the elimination of homoannulation

  苯甲酰胺和醛用于邻苯二甲酸酯合成的[4 +1]环化是通过rh催化的C–H活化而实现的，这证明了其与其他过渡金属催化剂截然不同的反应模式。该反应还具有容易获得的起始原料，对于富电和缺电的底物都有广泛的应用范围，并且消除了均环化副产物。
• 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。
• Rhodium or palladium-catalyzed cascade aryl addition/intramolecular lactonization of phthalaldehydonitrile to access 3-aryl and 3-alkenyl phthalides
  作者：Guanglei Lv、Genping Huang、Guangyou Zhang、Changduo Pan、Fan Chen、Jiang Cheng

  DOI：10.1016/j.tet.2011.04.100

  日期：2011.7

  A rhodium or palladium-catalyzed addition of boronic acids to phthalaldehydonitrile, followed by an intramolecular lactonization of cyano to access 3-substituted phthalides, is described. This procedure tolerates a series of functional groups, such as methoxy, fluoro, chloro, and vinyl groups. It is a novel procedure for the synthesis of 3-arylphthalides.

  描述了铑或钯催化的硼酸向邻苯二甲腈的加成，然后氰基的分子内酯化以得到3-取代的邻苯二甲酸酯。该程序容许一系列官能团，例如甲氧基，氟，氯和乙烯基。这是合成3-芳基邻苯二甲酸酯的新方法。
• Palladium-Catalyzed Cascade Aryl Addition/Intramolecular Lactonization of Phthalaldehyde To Access 3-Aryl- and Alkenylphthalides
  作者：Zhishi Ye、Pengcheng Qian、Guanglei Lv、Fang Luo、Jiang Cheng

  DOI：10.1021/jo101203b

  日期：2010.9.3

  A palladium-catalyzed addition of arylboronic acids to phthalaldehyde, followed by an intramolecular lactonization to access 3-substituted phthalides, is described. The procedure tolerates a series of functional groups, such as methoxyl, fluoro, chloro, and trifluoromethyl groups. It represents a procedure for the synthesis of 3-substituted phthalides.

  描述了钯催化的芳基硼酸加成至苯二甲醛中，然后进行分子内酯化以得到3-取代的苯二甲酸酯。该方法可耐受一系列官能团，例如甲氧基，氟，氯和三氟甲基。它代表了3-取代邻苯二甲酸酯的合成方法。