3-(4-methylphenyl)-3,4-dihydro-1H-isochromen-1-one | 95217-41-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-(4-methylphenyl)-3,4-dihydro-1H-isochromen-1-one
• 英文别名: 3-(p-Tolyl)-3,4-dihydro-1H-2-benzopyran-1-one；3-(4-methylphenyl)isochroman-1-one；3-p-tolyl-3,4-dihydroisocoumarin；1H-2-Benzopyran-1-one, 3,4-dihydro-3-(4-methylphenyl)-；3-(4-methylphenyl)-3,4-dihydroisochromen-1-one
• CAS: 95217-41-7
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: SARNCJFHLNJGJC-UHFFFAOYSA-N

物化性质

• 熔点：
  92-94 °C
• 沸点：
  415.3±44.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  2,2-二甲基-1-(2-甲基苯基)-1-丙酮 在 碘 、 mercury(II) oxide 、 lithium diisopropyl amide 作用下， 反应 0.08h， 生成 3-(4-methylphenyl)-3,4-dihydro-1H-isochromen-1-one
  参考文献：
  名称：

  Kobayashi, Kazuhiro; Konishi, Atsushi; Kanno, Yoshikazu, Journal of the Chemical Society. Perkin transactions I, 1993, # 1, p. 111 - 116

  摘要：

  DOI：

文献信息

• A Photocatalytic Meerwein Approach to the Synthesis of Isochromanones and Isochromenones
  作者：Stefano Crespi、Stefanie Jäger、Burkhard König、Maurizio Fagnoni

  DOI：10.1002/ejoc.201601458

  日期：2017.4.18

  A visible-light RuII photoredox Meerwein synthesis of isochromanones and isochromenones is described starting from diazonium salts of differently substituted anthranilic acids and various alkenes. This approach has allowed the reliable and efficient preparation of structures found in many biologically active molecules or used in materials chemistry.

  从不同取代的邻氨基苯甲酸和各种烯烃的重氮盐开始，描述了异色酮和异色酮的可见光 RuII photoredox Meerwein 合成。这种方法允许可靠和有效地制备在许多生物活性分子中发现或用于材料化学的结构。
• Metal‐ and Oxidant‐Free Electrosynthesis of Heterocycles from 1,2‐Diarylalkene Derivatives
  作者：Eunsoo Yu、Hyungguk Kim、Cheol‐Min Park

  DOI：10.1002/adsc.202200847

  日期：2022.12.8

  Synthesis of heterocycles from 1,2-diarylalkene derivatives through electrosynthesis under metal- and oxidant-free conditions has been discovered. Cathodic reduction of 2-alkenylbenzoic acid or anodic oxidation of 2-alkenylbenzamide, 2-alkenylphenol and 2-alkenylaniline leads to the formation of reactive radical intermediates which afford corresponding phthalide, isochroman-1-one, isoindolin-1-one

  已经发现在无金属和无氧化剂的条件下通过电合成从 1,2-二芳基烯烃衍生物合成杂环。2-烯基苯甲酸的阴极还原或 2-烯基苯甲酰胺、2-烯基苯酚和 2-烯基苯胺的阳极氧化导致反应性自由基中间体的形成，这些中间体提供相应的苯酞、异色满-1-酮、异吲哚啉-1-酮、苯并呋喃和吲哚以良好的官能团耐受性满足产量。有趣的是，在不同的反应溶剂中发现了不同的化学选择性。进行了几项机理研究，包括循环伏安法研究和控制实验，以阐明反应机理。
• Expeditious synthesis of 3,4-dihydroisocoumarins and phthalides using the Heck–Matsuda reaction
  作者：Eduardo T. da Penha、José Augusto Forni、André F.P. Biajoli、Carlos Roque D. Correia

  DOI：10.1016/j.tetlet.2011.09.014

  日期：2011.11

  Several 3,4-dihydroisocoumarins and phthalides were synthesized by an effective Heck-Matsuda reaction involving an ortho carboxybenzenediazonium salt with a series of styrenes bearing electron donating and electron withdrawing groups, methylvinyl ketone, and methyl acrylate. The reaction was carried out in an open-flask with 1% mol of palladium acetate in aqueous ethanol at similar to 80 degrees C, giving the correspondent 3-aryl-3,4-dihydroisocoumarins and phthalides with good overall yields. The electronic nature of the group attached to the olefin is a key feature for the regioselectivity of the cyclization step. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of 3-aryl-3,4-dihydroisocoumarins
  作者：Peter P. Fu、Leonard E. Unruh、Dwight W. Miller、Leo W. Huang、Dominic T. C. Yang

  DOI：10.1021/jo00208a020

  日期：1985.4
• Titanocene(III) chloride mediated radical-induced synthesis of 3,4-dihydroisocoumarins: synthesis of (±)-hydrangenol, (±)-phyllodulcin, (±)-macrophyllol and (±)-thunberginol G
  作者：Samir Kumar Mandal、Subhas Chandra Roy

  DOI：10.1016/j.tet.2008.09.075

  日期：2008.12

  A radical-promoted synthesis of 3,4-dihydroisocoumarins has been achieved in moderate to good yields using titanocene(III) chloride (Cp2TiCl) as the radical initiator. The total synthesis of four naturally occurring dihydrocoumarins hydrangenol, phyllodulcin, macrophyllol and thunberginol G has been accomplished using the radical technology. Cp2TiCl was prepared in situ from commercially available titanocene dichloride (Cp2TiCl2) and Zn-dust in THF under argon. (C) 2008 Elsevier Ltd. All rights reserved.