3,3'-(biphenyl-2,2'-diyl)di(pentan-3-ol) | 654052-44-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,3'-(biphenyl-2,2'-diyl)di(pentan-3-ol)
• 英文别名: 2,2'-bis(3-hydroxypentan-3-yl)biphenyl；2,2'-bis-(1-ethyl-1-hydroxy-propyl)-biphenyl；2,2'-Bis-(1-aethyl-1-hydroxy-propyl)-biphenyl；3-[2-[2-(3-Hydroxypentan-3-yl)phenyl]phenyl]pentan-3-ol
• CAS: 654052-44-5
• 化学式: C₂₂H₃₀O₂
• 分子量: 326.479
• InChiKey: QERMCVFXOODABB-UHFFFAOYSA-N

物化性质

• 熔点：
  98-99 °C
• 沸点：
  494.7±40.0 °C(predicted)
• 密度：
  1.032±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,3'-(biphenyl-2,2'-diyl)di(pentan-3-ol) 在 磷酸 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以93%的产率得到5,5,7,7-tetraethyl-5,7-dihydrodibenzo[c,e]oxepine
  参考文献：
  名称：

  2,2′-Dilithiobiphenyl by direct lithiation of biphenylene

  摘要：

  The reaction of biphenylene (1) with an excess of lithium powder (1:14 molar ratio) and a catalytic amount of DTBB (10 mol %) in THF at room temperature leads to the formation of the dilithiated species 1 by reductive opening of the four-membered ring. Further reaction of this intermediate with different electrophiles [Electrophile = H2O, D2O, Me3SiCl, t-BuCHO, Et2CO, n-Pr2CO, (CH2)(5)CO, Ph2CO and adamantanonel at 0 degrees C yields the corresponding products 2, after hydrolysis with water. Cyclisation of some representative examples of compounds 2 with H3PO4 gives the corresponding dibenzoxepines 3. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.216
• 作为产物：
  描述：

  3-戊酮 、 biphenyl-2,2'-diyl-bis-lithium 在 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 3,3'-(biphenyl-2,2'-diyl)di(pentan-3-ol)
  参考文献：
  名称：

  2,2′-Dilithiobiphenyl by direct lithiation of biphenylene

  摘要：

  The reaction of biphenylene (1) with an excess of lithium powder (1:14 molar ratio) and a catalytic amount of DTBB (10 mol %) in THF at room temperature leads to the formation of the dilithiated species 1 by reductive opening of the four-membered ring. Further reaction of this intermediate with different electrophiles [Electrophile = H2O, D2O, Me3SiCl, t-BuCHO, Et2CO, n-Pr2CO, (CH2)(5)CO, Ph2CO and adamantanonel at 0 degrees C yields the corresponding products 2, after hydrolysis with water. Cyclisation of some representative examples of compounds 2 with H3PO4 gives the corresponding dibenzoxepines 3. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.216

文献信息

• Structure, Conformation, Stereodynamics, Dimer Formation, and Absolute Configuration of Axially Chiral Atropisomers of Hindered Biphenyl Carbinols
  作者：Daniele Casarini、Lodovico Lunazzi、Michele Mancinelli、Andrea Mazzanti、Carlo Rosini

  DOI：10.1021/jo701481m

  日期：2007.9.1

  positions were found to exist as configurationally stable atropisomers: when R = Me (7) they were separated by enantioselective HPLC and the absolute configuration assigned on the basis of the corresponding CD spectra. In solution, compounds 6 (R = H) and 7 (R = Me) were found to originate a dimer, due to H-bond interactions between two enantiomers. In the case of 7, the free energy of activation (9.5 kcal

  在邻位带有单个CR 2 OH取代基的联苯衍生物的NMR光谱表明，由于绕Ar-CR 2 OH键的旋转受限制，它们以sp（更稳定）和ap（不稳定）构象异构体形式存在。当R ＝ Et（化合物2）时，通过低温NMR光谱的线形模拟确定相应的旋转势垒（7.5kcal mol -1）。在联苯的3'位置引入前手性i- Pr基团，在2（4）位具有CMe 2 OH取代基，从而可以确定对映异构体的阻隔层（由于Ar-Ar键旋转）而对轴向不稳定手性阻转异构体（13.9 5kcal mol -1）。这些壁垒的DFT计算均与实验一致。发现在2,2'位置带有两个CR 2 OH基团的联苯以构型稳定的阻转异构体形式存在：当R = Me（7）时，它们通过对映选择性HPLC分离，并根据相应的CD光谱确定了绝对构型。在溶液中，由于两种对映异构体之间的氢键相互作用，发现化合物6（R = H）和7（R = Me）引发了二聚体。在7的情况下，活化的自由能（9
• Corbellini; Vigano, Gazzetta Chimica Italiana, 1935, vol. 65, p. 735,738
  作者：Corbellini、Vigano

  DOI：——

  日期：——
• 2,2′-Dilithiobiphenyl by direct lithiation of biphenylene
  作者：Victor J. Lillo、Cecilia Gómez、Miguel Yus

  DOI：10.1016/j.tetlet.2009.02.216

  日期：2009.5

  The reaction of biphenylene (1) with an excess of lithium powder (1:14 molar ratio) and a catalytic amount of DTBB (10 mol %) in THF at room temperature leads to the formation of the dilithiated species 1 by reductive opening of the four-membered ring. Further reaction of this intermediate with different electrophiles [Electrophile = H2O, D2O, Me3SiCl, t-BuCHO, Et2CO, n-Pr2CO, (CH2)(5)CO, Ph2CO and adamantanonel at 0 degrees C yields the corresponding products 2, after hydrolysis with water. Cyclisation of some representative examples of compounds 2 with H3PO4 gives the corresponding dibenzoxepines 3. (C) 2009 Elsevier Ltd. All rights reserved.