3-(4-methoxyphenyl)-7-methyl-1H-isochromen-1-one | 1314961-52-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: 3-(4-methoxyphenyl)-7-methyl-1H-isochromen-1-one
• 英文别名: 3-(4-Methoxyphenyl)-7-methylisochromen-1-one
• CAS: 1314961-52-8
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: IGFCARNHLUDPCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  methyl 2-((4-methoxyphenyl)ethynyl)-5-methylbenzoate 在 iron(III) chloride 作用下， 以 二氯甲烷 为溶剂， 以54%的产率得到3-(4-methoxyphenyl)-7-methyl-1H-isochromen-1-one
  参考文献：
  名称：

  Regioselective Synthesis of Isochromenones by Iron(III)/PhSeSePh-Mediated Cyclization of 2-Alkynylaryl Esters

  摘要：

  A series of 4-Se-(Te, S)-isochromenones and 3-substituted isochromenones were synthesized in good yields via FeCl3-mediated cyclization of alkynylaryl esters with different diorganyl dichalcogenides. This methodology was carried out at room temperature, using inexpensive and environmentally friendly iron salts as metallic source and under air atmosphere. The reaction showed to be tolerant to a range of substituents bonded into the aromatic ring of the diorganyl dichalcogenides as well as to alkyl groups directly bonded to the chalcogen atom. Alternatively, the cyclization reaction of 2-alkynylaryl esters with FeCl3, in the absence of diorganyl dichalcogenide, gave the isochromenones without the chalcogen moiety in the structure. This approach proved to be highly regioselective, providing only six-membered ring products, once the possible five-membered products were not observed in any experiments.

  DOI：

  10.1021/jo201211s

文献信息

• Regioselective cyclization of 2-alkynylbenzoic acid in water for the synthesis of isocoumarin
  作者：Yan-Hua Wang、Guanyinsheng Qiu、Hongwei Zhou、Wenlin Xie、Jin-Biao Liu

  DOI：10.1016/j.tet.2019.06.012

  日期：2019.7

  In this work, a regioselective synthesis of isocoumarins from 2-alkynylbenzoic acid is reported. The transformations proceed smoothly with good yields in water via a metal-free radical pathway. When catalytic TBAB is employed, the reaction provides various isocoumarin derivatives according to the structures of the corresponding precursors. It is believed that TBAB serves as a phase transfer catalyst

  在这项工作中，据报道由2-炔基苯甲酸区域选择性合成异香豆素。通过金属自由基途径，转化过程顺利进行，并在水中产生高收率。当使用催化TBAB时，反应根据相应前体的结构提供各种异香豆素衍生物。据信TBAB在反应中用作相转移催化剂和自由基引发剂。与以前的方法相比，本文报道的合成方法为异香豆素的合成提供了更环境友好的途径。
• Water mediated NHC-Pd (II) catalyzed oxidative coupling of benzoic acid and vinylarenes; Selective synthesis of five/six member isocoumarins
  作者：Lalit Negi、Aditi Soni、Manisha、Charu Sharma、Raj K. Joshi

  DOI：10.1016/j.jorganchem.2023.122847

  日期：2023.11

  Herein, a selective synthesis of isocoumarin and 3-benzylidenephthalides via Heck-type ortho-olefination of benzoic acids with vinyl arenes is reported under the mild reaction protocols. The present reaction was catalyzed by a well-established selenated NHC-Pd(II) pincer complex and Ag(OAc) as an oxidant. All reactions work in water, which is a green eco-friendly solvent; moreover, the method's effectiveness

  在此，通过 Heck 型邻位选择性合成异香豆素和 3-亚苄基苯酞据报道，苯甲酸与乙烯基芳烃的烯化反应是在温和的反应方案下进行的。本反应由成熟的硒化 NHC-Pd(II) 钳配合物和 Ag(OAc) 作为氧化剂催化。所有反应均在水中进行，水是一种绿色环保溶剂；此外，该方法的有效性通过选择性合成异香豆素或3-亚苄基苯酞以中等至良好的收率而得到凸显。与苯甲酸和乙烯基芳烃相关的官能团没有表现出任何有害影响并显示了该方案的功效。简而言之，本发明的苯甲酸和乙烯基芳烃的氧化偶联方法需要较低量的催化剂和氧化剂负载，与绿色溶剂水有效配合，并在有氧条件下在12-14小时内产生选择性异香豆素产物。
• Palladium-Catalyzed Cascade Cyclization–Oxidative Olefination of <i>tert</i>-Butyl 2-Alkynylbenozates
  作者：Peng Zhao、Dan Chen、Guoyong Song、Keli Han、Xingwei Li

  DOI：10.1021/jo202228k

  日期：2012.2.3

  Palladium(II) can catalyze the oxidative coupling of tert-butyl 2-alkynylbenzoates with olefins such as acrylates and styrenes, leading to isocoumarines. The reaction was carried out under simple aerobic conditions, and in most cases, high selectivity has been attained.
• Regioselective Synthesis of Isochromenones by Iron(III)/PhSeSePh-Mediated Cyclization of 2-Alkynylaryl Esters
  作者：Adriane Sperança、Benhur Godoi、Simone Pinton、Davi F. Back、Paulo H. Menezes、Gilson Zeni

  DOI：10.1021/jo201211s

  日期：2011.8.19

  A series of 4-Se-(Te, S)-isochromenones and 3-substituted isochromenones were synthesized in good yields via FeCl3-mediated cyclization of alkynylaryl esters with different diorganyl dichalcogenides. This methodology was carried out at room temperature, using inexpensive and environmentally friendly iron salts as metallic source and under air atmosphere. The reaction showed to be tolerant to a range of substituents bonded into the aromatic ring of the diorganyl dichalcogenides as well as to alkyl groups directly bonded to the chalcogen atom. Alternatively, the cyclization reaction of 2-alkynylaryl esters with FeCl3, in the absence of diorganyl dichalcogenide, gave the isochromenones without the chalcogen moiety in the structure. This approach proved to be highly regioselective, providing only six-membered ring products, once the possible five-membered products were not observed in any experiments.