3-butyl-7-fluoro-1H-isochromen-1-one | 1159371-88-6

• 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-butyl-7-fluoro-1H-isochromen-1-one
• 英文别名: 3-n-butyl-7-fluoroisocoumarin；3-Butyl-7-fluoroisochromen-1-one
• CAS: 1159371-88-6
• 化学式: C₁₃H₁₃FO₂
• 分子量: 220.243
• InChiKey: LGCSTJDGGILJEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(1-iodopentylidene)benzo[e][2]benzofuran-3-one 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 3-butyl-7-fluoro-1H-isochromen-1-one
  参考文献：
  名称：

  Solid-Phase Synthesis of Isocoumarins: A Traceless Halocyclization Approach

  摘要：

  A straightforward and traceless solid-phase methodology was developed for the synthesis of isocournarins. This two-step process involves a Sonogashira cross-coupling reaction between polymer-bound 2-bromobenzoates and terminal alkynes, followed by an electrophile-induced halocyclization of the resulting 2-(alk-1-ynyl)benzoates through activation of the triple bond with the subsequent release of the 3-substituted 4-haloisocoumarins. This polymer-bound parallel synthetic approach allowed us to achieve large diversity in good to excellent yields and purities.

  DOI：

  10.1021/jo900281a

文献信息

• NHC-Catalyzed Oxidative Cyclization Reactions of 2-Alkynylbenzaldehydes under Aerobic Conditions: Synthesis of O-Heterocycles
  作者：Jong Hyub Park、Sachin V. Bhilare、So Won Youn

  DOI：10.1021/ol200481u

  日期：2011.5.6

  An NHC-catalyzed, regio- and stereoselective oxidative cyclization of o-alkynylbenzaldehydes bearing an unactivated alkyne moiety as an internal electrophile has been developed to afford phthalides and isocoumarins. A single organocatalytic system enabled two sequential C−O bond formations to take place in an atom economical manner via highly efficient dual activation. Molecular oxygen in air could

  已开发出具有NHC催化，带有未活化炔烃部分的邻炔基苯甲醛作为内部亲电子试剂的区域和立体选择性氧化环化反应，以提供邻苯二甲酸酯和异香豆素。单一的有机催化系统通过高效的双重活化，以原子经济的方式使两个连续的C-O键形成成为可能。在我们新开发的试剂系统下，空气中的分子氧可以用作氧原子的来源，用于将醛氧化为相应的苯甲酸。
• Solid-Phase Synthesis of Isocoumarins: A Traceless Halocyclization Approach
  作者：Marine Peuchmaur、Vincent Lisowski、Céline Gandreuil、Ludovic T. Maillard、Jean Martinez、Jean-François Hernandez

  DOI：10.1021/jo900281a

  日期：2009.6.5

  A straightforward and traceless solid-phase methodology was developed for the synthesis of isocournarins. This two-step process involves a Sonogashira cross-coupling reaction between polymer-bound 2-bromobenzoates and terminal alkynes, followed by an electrophile-induced halocyclization of the resulting 2-(alk-1-ynyl)benzoates through activation of the triple bond with the subsequent release of the 3-substituted 4-haloisocoumarins. This polymer-bound parallel synthetic approach allowed us to achieve large diversity in good to excellent yields and purities.