methyl 4-((9H-fluoren-9-ylidene)(phenyl)methyl)benzoate | 1600505-47-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: methyl 4-((9H-fluoren-9-ylidene)(phenyl)methyl)benzoate
• 英文别名: Methyl 4-[fluoren-9-ylidene(phenyl)methyl]benzoate；methyl 4-[fluoren-9-ylidene(phenyl)methyl]benzoate
• CAS: 1600505-47-2
• 化学式: C₂₈H₂₀O₂
• 分子量: 388.466
• InChiKey: UDASWCCFGDNCDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 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：

  dibenzo[b,d]iodol-5-ium trifluoromethanesulfonate 、 苯乙炔 、 4-甲氧羰基苯硼酸 在 copper(l) iodide 、 palladium diacetate 、 sodium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以81%的产率得到methyl 4-((9H-fluoren-9-ylidene)(phenyl)methyl)benzoate
  参考文献：
  名称：

  Three-Component Pd/Cu-Catalyzed Cascade Reactions of Cyclic Iodoniums, Alkynes, and Boronic Acids: An Approach to Methylidenefluorenes

  摘要：

  Linear diaryliodonium salts are widely used as arylating reagents for C-C and C-X bond formation. Meanwhile, synthetic applications of cyclic iodoniums are relatively rare although they offer the opportunity to set up reaction cascades. We demonstrate an atom and step economical three-component reaction involving cyclic diphenyleneiodoniums, alkynes, and boronic acids, resulting in the construction of methylidenefluorenes in a single operation. Our route enables facile access to both symmetrical and unsymmetrical methylidenefluorene derivatives, compounds that have attracted interest due to their optical properties.

  DOI：

  10.1021/ol5006714

文献信息

• Three-Component Pd/Cu-Catalyzed Cascade Reactions of Cyclic Iodoniums, Alkynes, and Boronic Acids: An Approach to Methylidenefluorenes
  作者：Daqian Zhu、Yongcheng Wu、Baojian Wu、Bingling Luo、A. Ganesan、Fu-Hai Wu、Rongbiao Pi、Peng Huang、Shijun Wen

  DOI：10.1021/ol5006714

  日期：2014.5.2

  Linear diaryliodonium salts are widely used as arylating reagents for C-C and C-X bond formation. Meanwhile, synthetic applications of cyclic iodoniums are relatively rare although they offer the opportunity to set up reaction cascades. We demonstrate an atom and step economical three-component reaction involving cyclic diphenyleneiodoniums, alkynes, and boronic acids, resulting in the construction of methylidenefluorenes in a single operation. Our route enables facile access to both symmetrical and unsymmetrical methylidenefluorene derivatives, compounds that have attracted interest due to their optical properties.