spiro-1,1-(2,2'-biphenyl)-2-(2-indenyl)indane | 398128-08-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: spiro-1,1-(2,2'-biphenyl)-2-(2-indenyl)indane
• 英文别名: Spiro[9H-fluorene-9,2'-[2H]indene], 1',3'-dihydro-1'-(1H-inden-2-yl)-；1-(1H-inden-2-yl)spiro[1,3-dihydroindene-2,9'-fluorene]
• CAS: 398128-08-0
• 化学式: C₃₀H₂₂
• 分子量: 382.505
• InChiKey: NOAGMIUJZKPXNV-UHFFFAOYSA-N

物化性质

• 熔点：
  158-159 °C
• 沸点：
  501.6±50.0 °C(predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2-溴化茚 在 四(三苯基膦)钯 、 potassium carbonate 、 magnesium 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 为溶剂， 反应 19.25h， 生成 spiro-1,1-(2,2'-biphenyl)-2-(2-indenyl)indane
  参考文献：
  名称：

  A Suzuki Coupling Based Route to 2,2‘-Bis(2-indenyl)biphenyl Derivatives

  摘要：

  Because of the promising performance in olefin polymerization of 2,2'-bis(2-indenyldiyl)biphenyl zirconium dichloride, we developed a new and broadly applicable route to 2,2'-bis(2-indenyl)biphenyl derivatives. Reaction of the known 2,2'-diiodobiphenyl (26) with the new 2-indenyl boronic acid (23) did not result in the desired 2,2'-bis(2-indenyl)biphenyl (10); instead an isomer thereof, (spiro-1,1-(2,2'-biphenyl)-2-(2-indenyl)indane) (27), was obtained. It was found that compound 10 could be made via a palladium-catalyzed reaction of 2,2-biphenyldiboronic acid (31) with 2-bromoindene (21) under standard Suzuki reaction conditions. However, the yield of this reaction was low at low palladium catalyst loadings, due to a competitive hydrolysis reaction of 2,2-biphenyldiboronic acid (31). HTE techniques were used to find an economically viable protocol. Thus, use of the commercially available 1.0 molar solution of (n-BU)(4)NOH in methanol with cosolvent toluene led to precipitation of the pure product in a fast and clean reaction, using only 0.7 mol % (0.35 mol % per C-C) of the expensive palladium catalyst.

  DOI：

  10.1021/jo016040i

文献信息

• A Suzuki Coupling Based Route to 2,2‘-Bis(2-indenyl)biphenyl Derivatives
  作者：Edwin G. IJpeij、Felix H. Beijer、Henricus J. Arts、Claire Newton、Johannes G. de Vries、Gert-Jan M. Gruter

  DOI：10.1021/jo016040i

  日期：2002.1.1

  Because of the promising performance in olefin polymerization of 2,2'-bis(2-indenyldiyl)biphenyl zirconium dichloride, we developed a new and broadly applicable route to 2,2'-bis(2-indenyl)biphenyl derivatives. Reaction of the known 2,2'-diiodobiphenyl (26) with the new 2-indenyl boronic acid (23) did not result in the desired 2,2'-bis(2-indenyl)biphenyl (10); instead an isomer thereof, (spiro-1,1-(2,2'-biphenyl)-2-(2-indenyl)indane) (27), was obtained. It was found that compound 10 could be made via a palladium-catalyzed reaction of 2,2-biphenyldiboronic acid (31) with 2-bromoindene (21) under standard Suzuki reaction conditions. However, the yield of this reaction was low at low palladium catalyst loadings, due to a competitive hydrolysis reaction of 2,2-biphenyldiboronic acid (31). HTE techniques were used to find an economically viable protocol. Thus, use of the commercially available 1.0 molar solution of (n-BU)(4)NOH in methanol with cosolvent toluene led to precipitation of the pure product in a fast and clean reaction, using only 0.7 mol % (0.35 mol % per C-C) of the expensive palladium catalyst.