methyl 2-((4-methoxyphenyl)ethynyl)-5-methylbenzoate | 1314961-44-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-((4-methoxyphenyl)ethynyl)-5-methylbenzoate
• CAS: 1314961-44-8
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: XORKDLWEPJAKPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 2-((4-methoxyphenyl)ethynyl)-5-methylbenzoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 生成
  参考文献：
  名称：

  Concise Route to 3-Arylisoquinoline Skeleton by Lewis Acid Catalyzed C(sp³)–H Bond Functionalization and Its Application to Formal Synthesis of (±)-Tetrahydropalmatine

  摘要：

  An expeditious route to furnish an isoquinoline skeleton via hydride shift mediated C-H bond functionalization was developed. In this process, an unusual [1,5]-H shift without the assistance of the adjacent heteroatom took place to produce tetrahydroisoquinoline derivatives in good to excellent chemical yields. The formal synthesis of (+/-)-tetrahydropalmatine was achieved by exploiting this new transformation.

  DOI：

  10.1021/ol300180w
• 作为产物：
  描述：

  2-碘-5-甲基苯甲酸甲酯 、 4-乙炔基苯甲醚 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以76 %的产率得到methyl 2-((4-methoxyphenyl)ethynyl)-5-methylbenzoate
  参考文献：
  名称：

  从 2-乙炔基苯甲酸酯直接合成双[(三氟甲基)磺酰基]乙基化异香豆素

  摘要：

  在此，我们报告了一种简便的异香豆素和异喹诺酮制剂，利用初始双（三氟甲基）乙基化 [三氟甲基 =（三氟甲基）磺酰基] 反应，然后进行杂环化，这与我们之前关于环丁烯形成的结果形成对比。无催化剂和无辐射的杂环化/双（三氟甲基）乙基化序列的效率显示出对 2-苯甲酸乙炔酯（苯甲酰胺）前体取代基的电子性质的精确依赖性。模型双（三氟甲基）乙基化异香豆素与人乙酰胆碱酯酶 (hAChE) 的分子对接通过催化活性位点和外周活性位点的选择性协调揭示了有前途的生物活性。

  DOI：

  10.1021/acs.joc.3c00611

文献信息

• 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.