4-(butyltellurenyl)-3-phenyl-1H-isochromen-1-one | 1314961-37-9

• 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: 4-(butyltellurenyl)-3-phenyl-1H-isochromen-1-one
• 英文别名: 4-Butyltellanyl-3-phenylisochromen-1-one
• CAS: 1314961-37-9
• 化学式: C₁₉H₁₈O₂Te
• 分子量: 405.951
• InChiKey: HUMZZAUIRWFNFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  二丁基二碲 、 2-苯基乙炔基苯甲酸甲酯 在 iron(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 18.33h， 以35%的产率得到4-(butyltellurenyl)-3-phenyl-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 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.