5-methoxy-7-methylisobenzofuran-1(3H)-one | 110451-92-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 5-methoxy-7-methylisobenzofuran-1(3H)-one
• 英文别名: 5-methoxy-7-methylphthalide；5-methoxy-7-methyl-3H-2-benzofuran-1-one
• CAS: 110451-92-8
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: FOFRWIFYUYCDDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methoxy-7-methylisobenzofuran-1(3H)-one 在 potassium cyanide 、 18-冠醚-6 、 碘代三甲硅烷 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 34.0h， 生成 4-hydroxy-2,9-dimethoxy-7,12,12-trimethyltetracene-5,6,11(12H)-trione
  参考文献：
  名称：

  Total Synthesis of Tetarimycin A, (±)-Naphthacemycin A₉, and (±)-Fasamycin A: Structure–Activity Relationship Studies against Drug-Resistant Bacteria

  摘要：

  Making use of a reductive olefin coupling reaction and Michael-Dieckmann condensation as two key operations, we have completed a concise total synthesis of tetarimycin A, (+/-)-naphthacemycin A(9), and (+/-)-fasamycin A in a highly convergent and practical protocol. Synthetic procedures thus developed have also been applied to provide related analogues for structure-activity relationship studies, thereby coming to the conclusion that the free hydroxyl group at C-10 is essential for exerting inhibitory activities against a panel of Gram-positive bacteria, including drug-resistant strains VRE and MRSA.

  DOI：

  10.1021/acs.joc.8b00802
• 作为产物：
  描述：

  3,5-二甲氧基苄醇 在 2-双环己基膦-2',6'-二甲氧基联苯 、 吡啶 、 tris-(dibenzylideneacetone)dipalladium(0) 、 三氯化硼 、 sodium carbonate 、 三氯氧磷 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 16.5h， 生成 5-methoxy-7-methylisobenzofuran-1(3H)-one
  参考文献：
  名称：

  Total Synthesis of Tetarimycin A, (±)-Naphthacemycin A₉, and (±)-Fasamycin A: Structure–Activity Relationship Studies against Drug-Resistant Bacteria

  摘要：

  Making use of a reductive olefin coupling reaction and Michael-Dieckmann condensation as two key operations, we have completed a concise total synthesis of tetarimycin A, (+/-)-naphthacemycin A(9), and (+/-)-fasamycin A in a highly convergent and practical protocol. Synthetic procedures thus developed have also been applied to provide related analogues for structure-activity relationship studies, thereby coming to the conclusion that the free hydroxyl group at C-10 is essential for exerting inhibitory activities against a panel of Gram-positive bacteria, including drug-resistant strains VRE and MRSA.

  DOI：

  10.1021/acs.joc.8b00802

文献信息

• Visible Light-Promoted Magnesium, Iron, and Nickel Catalysis Enabling C(sp³)–H Lactonization of 2-Alkylbenzoic Acids
  作者：Sasa Li、Mincong Su、Jie Sun、Kunjun Hu、Jian Jin

  DOI：10.1021/acs.orglett.1c01984

  日期：2021.8.6

  patterns could be transformed into the corresponding phthalide products. Based on the mechanistic experimentation and reported prior studies, a possible mechanism for the benzylic oxidative lactonization reaction was proposed with the hypothetic photoactive ternary complex formed between the 2-alkylbenzoic acid substrate, magnesium ion, and bromate anion.

  通过合并光催化和镁（铁、镍）催化，实现了温和实用的 C(sp 3 )-H 内酯化方案。具有多种取代模式的多种 2-烷基苯甲酸可以转化为相应的邻苯二甲酸产品。基于机理实验和先前报道的研究，提出了苄基氧化内酯化反应的可能机制，假设光活性三元络合物在 2-烷基苯甲酸底物、镁离子和溴酸盐阴离子之间形成。
• Transpositive Tandem Annulation of Phthalides with Allene Carboxylates: Regioselective Synthesis of Arylnaphthalene Lignans
  作者：Dipakranjan Mal、Supriti Jana

  DOI：10.1021/acs.joc.6b02313

  日期：2016.12.2

  Allene carboxylates, scarcely used as Michael acceptors, serve as acceptors in the annulation with phthalides in the presence of LDA and provide a one-pot synthesis of naphtho[c]furanones in very good yields. This tandem annulation is proposed to proceed via transposition of the hydroxy group resulting from the initial annulation.

  几乎不用作迈克尔受体的丙二烯羧酸盐在LDA存在下与邻苯二甲酸酯成环时用作受体，并以非常高的收率提供一锅法合成萘并[ c ]呋喃酮。提出这种串联环化是通过由初始环化产生的羟基的转位进行的。
• Synergistic Palladium-Catalyzed C(sp3)H Activation/C(sp3)O Bond Formation: A Direct, Step-Economical Route to Benzolactones
  作者：Petr Novák、Arkaitz Correa、Joan Gallardo-Donaire、Ruben Martin

  DOI：10.1002/anie.201105894

  日期：2011.12.16

  Simplified access: Substituted benzolactones can be obtained in one step by a Pd‐catalyzed ligand‐accelerated C(sp3)H bond‐activation/C(sp3)O bond‐formation protocol. This step‐economical approach enables the preparation of benzolactones with a wide variety of functional groups and different substitution patterns. The method is characterized by its simplicity and the avoidance of protecting groups

  简化访问：取代的benzolactones可以在一个步骤通过Pd催化的配体加速C（SP来获得3） H键活化/ C（SP 3） O键-形成协议。这种分步经济的方法可以制备具有多种官能团和不同取代方式的苯甲内酯。该方法的特征在于其简单性和避免了保护基团。
• Syntheses and Redox Properties of Carboxylate-Ligated Hexanuclear Ce(IV) Clusters and Their Photoinduced Homolysis of the Ce(IV)–Ligand Covalent Bond
  作者：Tomomi Kawakami、Sota Tamaki、Satoru Shirase、Hayato Tsurugi、Kazushi Mashima

  DOI：10.1021/acs.inorgchem.2c03163

  日期：2022.12.19

  hydroxo-bridged hexanuclear Ce(IV) clusters surrounded by 12 carboxylate ligands, Ce6O4(OH)4(O2CR)12(L)n (R = 2,6-Me2-4-MeOC6H2 (1a), 2,6-Me2-4-tBuC6H2 (1b), 2,4,6-Me3C6H2 (1c), 2,6-Me2C6H3 (1d), 2,6-Me2-4-FC6H2 (1e), 2,6-Me2-4-ClC6H2 (1f), 9-anthracenyl (1g), and CH2tBu (1h), L = H2O or RCO2H), were synthesized by treating Ce(OtBu)4 with the corresponding carboxylic acids (2–3 equiv.) in acetone or toluene, and

  氧代和羟基桥接的六核 Ce(IV) 簇被 12 个羧酸配体包围，Ce 6 O 4 (OH) 4 (O 2 CR) 12 (L) n (R = 2,6-Me 2 -4-MeOC 6 H 2 ( 1a ), 2,6-Me 2 -4- t BuC 6 H 2 ( 1b ), 2,4,6-Me 3 C 6 H 2 ( 1c ), 2,6-Me 2 C 6 H 3 ( 1d ), 2,6-Me 2 -4-FC6 H 2 ( 1e ), 2,6-Me 2 -4-ClC 6 H 2 ( 1f ), 9-蒽基 ( 1g ), CH 2 t Bu ( 1h ), L = H 2 O or RCO 2 H) ，通过在丙酮或甲苯中用相应的羧酸（2-3当量）处理Ce（O t Bu）4来合成，以及1d和1g的分子结构已通过 X 射线衍射研究得到澄清。团簇的 UV-vis 分析显示，对应于紫外线 A（315-400
• Studies on Antibiotics Active against Resistant Bacteria. Total Synthesis of MRSA-Active Tetarimycin A and Its Analogues
  作者：Jing-Kai Huang、Tsai-Ling Yang Lauderdale、Kak-Shan Shia

  DOI：10.1021/acs.orglett.5b02039

  日期：2015.9.4

  Making use of the Hauser-Kraus annulation as a key step, the first total synthesis of tetarimycin A has been accomplished in a highly convergent and operationally simple manner. Preliminary SAR not only validated that tetarimycin A exhibited potent activity against MRSA and VRE at a low MIC value but also identified that the hydroxyl group at C-10 was essential for antibacterial activities.