7-methyl-3-phenyl-4-(phenylselenyl)-1H-isochromen-1-one | 1314961-28-8

• 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: 7-methyl-3-phenyl-4-(phenylselenyl)-1H-isochromen-1-one
• 英文别名: 7-Methyl-3-phenyl-4-phenylselanylisochromen-1-one
• CAS: 1314961-28-8
• 化学式: C₂₂H₁₆O₂Se
• 分子量: 391.328
• InChiKey: HTTPMPBGPAGPAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  二苯基二硒醚 在 (二氯碘)-苯 作用下， 以 正己烷 、 乙腈 为溶剂， 反应 0.58h， 生成 7-methyl-3-phenyl-4-(phenylselenyl)-1H-isochromen-1-one
  参考文献：
  名称：

  RSCl / ArSeCl的原位形成及其在邻-（1-炔基）苯甲酸酯和（Z）-2-Alken-4-yanoates合成4-硫属异氰酸酯/吡喃酮中的应用

  摘要：

  首次发现二有机基二硫化物或二硒化物与PhICl 2在乙腈中的反应导致原位形成有机亚磺酰氯或亚硒基氯，这使炔的区域选择性分子内硫属半乳糖基酰氧基化反应导致形成4-硫属元素基异cumarins /吡喃酮。在无金属条件下的收率好至极好。

  DOI：

  10.1021/acs.orglett.9b01046

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.
• In Situ Formation of RSCl/ArSeCl and Their Application to the Synthesis of 4-Chalcogenylisocumarins/Pyrones from <i>o</i>-(1-Alkynyl)benzoates and (<i>Z</i>)-2-Alken-4-ynoates
  作者：Linlin Xing、Yong Zhang、Bing Li、Yunfei Du

  DOI：10.1021/acs.orglett.9b01046

  日期：2019.5.17

  diorganyl disulfides or diselenides with PhICl2 in acetonitrile was found for the first time to lead to the in situ formation of organosulfenyl chloride or selenenyl chloride, which enables the regioselective intramolecular chalcogenylacyloxylation of alkynes resulting in the formation of 4-chalcogenylisocumarins/pyrones in good to excellent yields under metal-free conditions.

  首次发现二有机基二硫化物或二硒化物与PhICl 2在乙腈中的反应导致原位形成有机亚磺酰氯或亚硒基氯，这使炔的区域选择性分子内硫属半乳糖基酰氧基化反应导致形成4-硫属元素基异cumarins /吡喃酮。在无金属条件下的收率好至极好。