3-(3-methoxyphenyl)-3,4-dihydroisocoumarin | 81428-86-6

• 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-(3-methoxyphenyl)-3,4-dihydroisocoumarin
• 英文别名: 1H-2-Benzopyran-1-one, 3,4-dihydro-3-(3-methoxyphenyl)-；3-(3-methoxyphenyl)-3,4-dihydroisochromen-1-one
• CAS: 81428-86-6
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: LSDOXZVQSCOELV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N,N-二乙基-2-甲基苯甲酰胺 在 sodium hydroxide 、 lithium diisopropyl amide 作用下， 以 乙醇 、 水 为溶剂， 反应 17.0h， 生成 3-(3-methoxyphenyl)-3,4-dihydroisocoumarin
  参考文献：
  名称：

  Ortho-lithiated tertiary benzamides. Chain extension via o-toluamide anion and general synthesis of isocoumarins including hydrangenol and phyllodulcin

  摘要：

  DOI：

  10.1021/jo00179a002

文献信息

• Metal-Free Addition of Benzyl Halides to Aldehydes Using Super Electron Donors: Access to 3,4-Dihydroisocoumarins and 1,2-Diarylethanols
  作者：Cédric Spitz、Mélanie Matteudi、Guillaume Tintori、Julie Broggi、Thierry Terme、Patrice Vanelle

  DOI：10.1021/acs.joc.0c02374

  日期：2020.12.4

  We report here the intermolecular metal-free addition reaction of functionalized benzyl halides to aldehydes using a super electron donor (SED). The metal-free and mild conditions allowed the formation of 3,4-dihydroisocoumarins and 1,2-diarylethanols with unprecedented functional group tolerance.

  我们在这里报告使用超电子给体（SED）的官能化苄基卤化物与醛的无分子间金属加成反应。无金属且温和的条件允许形成具有前所未有的官能团耐受性的3,4-二氢异香豆素和1,2-二芳基乙醇。
• Total synthesis of homalicine and its related dihydro aglycon
  作者：Khosrow Zamani、Nasim Hassan Rama、Rashid Iqbal

  DOI：10.1002/jhet.5570370641

  日期：2000.11

  3-methoxybenzoyl chloride, followed by demethylation gave 3-(3-hydroxyphenyl)isocoumarin (3b). Reaction of (3b) with α-tetraacetobromo glucose yielded tetraacetylhomalicine (3d), which was deacetylated to homalicine (3e).

  高邻苯二甲酸（1）与3-甲氧基苯甲酰氯的缩合，然后脱甲基，得到3-（3-羟苯基）异香豆素（3b）。（3b）与α-四乙酰溴葡萄糖的反应产生了四乙酰基尿嘧啶（3d），其被脱乙酰化为尿嘧啶（3e）。
• Chromium/Photoredox Dual Catalyzed Synthesis of <i>α</i> ‐Benzylic Alcohols, Isochromanones, 1,2‐Oxy Alcohols and 1,2‐Thio Alcohols
  作者：Subhabrata Dutta、Johannes E. Erchinger、Felix Schäfers、Ankita Das、Constantin G. Daniliuc、Frank Glorius

  DOI：10.1002/anie.202212136

  日期：2022.12.5

  The synthesis of α-benzylic alcohols, functionalized isochromanones, 1,2-oxy alcohols and 1,2-thio alcohols has been successfully achieved by employing a dual catalytic method combining chromium chemistry and photoredox catalysis. This presents a methodology under mild conditions with high functional group tolerance.

  通过采用结合铬化学和光氧化还原催化的双重催化方法，成功合成了α-苄醇、官能化异色满酮、1,2-羟基醇和 1,2-硫醇。这提出了一种在温和条件下具有高官能团耐受性的方法。
• Addition of Benzyl Halides to Aldehydes and Imines Using Photoactivated TDAE: Access to 3,4-Dihydroisocoumarins, 1,2-Diarylethanols, and 1,2-Diarylcarbamates under Metal-Free Conditions
  作者：Cédric Spitz、Morgane Bertrand、Vincent Remusat、Thierry Terme、Patrice Vanelle

  DOI：10.1021/acs.joc.2c00074

  日期：2022.3.18

  We describe herein the intermolecular addition reaction of benzyl halides to aldehydes and imines using photoactivated tetrakis(dimethylamino)ethylene (TDAE) as superphotoreductant. 3,4-Dihydroisocoumarins, 1,2-diarylethanols, and 1,2-diarylcarbamates were obtained with good functional group tolerance using simple, mild, and metal-free conditions.

  我们在此描述了使用光活化四(二甲氨基) 乙烯 (TDAE) 作为超光还原剂的苄基卤化物与醛和亚胺的分子间加成反应。3,4-二氢异香豆素、1,2-二芳基乙醇和1,2-二芳基氨基甲酸酯在简单、温和和无金属条件下获得了良好的官能团耐受性。
• Electron-Transfer-Induced Reductive Cleavage of Phthalans:  Reactivity and Synthetic Applications
  作者：Ugo Azzena、Salvatore Demartis、Giovanni Melloni

  DOI：10.1021/jo9604548

  日期：1996.1.1

  The behavior of phthalan (1a) was investigated under conditions of electron transfer from alkali metals in aprotic solvents. Reaction with lithium in the presence of a catalytic amount of naphthalene in THF led to the reductive cleavage of an arylmethyl carbon-oxygen bond, with formation of a stable dilithium compound. Trapping of this intermediate with several electrophiles (alkyl halides, carbonyl derivatives, CO2) was successful. The extension of this procedure to several substituted phthalans (1b-i) was investigated, and the regiochemistry as well as the synthetic usefulness of these reactions are discussed.