2-(3-Fluorophenyl)-7-methyl-4H-chromen-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(3-Fluorophenyl)-7-methyl-4H-chromen-4-one
• 英文别名: 2-(3-fluorophenyl)-7-methylchromen-4-one
• 化学式: C₁₆H₁₁FO₂
• 分子量: 254.261
• InChiKey: MROIBHULTUGBPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  [2-[3-(3-Fluorophenyl)prop-2-ynoyl]-5-methylphenyl] acetate 在 哌嗪 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以95%的产率得到2-(3-Fluorophenyl)-7-methyl-4H-chromen-4-one
  参考文献：
  名称：

  Pd catalyzed couplings of “superactive esters” and terminal alkynes: Application to flavones and γ-benzopyranones construction

  摘要：

  Lewis base, N-methylmorpholine (NMM) accelerated Pd-catalyzed Sonogashira coupling of steric hindered super active esters, la-le, and terminal alkynes. This approach provided an efficient synthetic protocol for a broad array of acylated o-alkynoylphenols compounds, 3a-3e, under moderate conditions. The mechanistic study clearly demonstrated that NNM stabilized the catalytic palladium species, and accelerated the leaving of triazine moiety during the catalytic cycle of the cross-coupling reactions. In addition, piperazine was found to efficiently catalyze the 6-endo cyclization of acylated o-alkynoylphenols, which achieved the diversity oriented synthesis of gamma-benzopyranones, 4aa-4eg, with 93-99% yields. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2016.10.030