2,6-bis(2,6-diisopropylphenyl)benzyl alcohol | 753014-58-3

• 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: 2,6-bis(2,6-diisopropylphenyl)benzyl alcohol
• 英文别名: [2,6-Bis[2,6-di(propan-2-yl)phenyl]phenyl]methanol
• CAS: 753014-58-3
• 化学式: C₃₁H₄₀O
• 分子量: 428.658
• InChiKey: YHHIZOKKYPQBFD-UHFFFAOYSA-N

物化性质

• 熔点：
  193-196 °C(Solv: hexane (110-54-3))
• 沸点：
  562.0±50.0 °C(Predicted)
• 密度：
  0.987±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,6-bis(2,6-diisopropylphenyl)benzyl alcohol 在 氢溴酸 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以45%的产率得到3-[[2,6-Bis[2,6-di(propan-2-yl)phenyl]phenyl]methyl]-1,5-bis[2,6-di(propan-2-yl)phenyl]-6-methylidenecyclohexa-1,4-diene
  参考文献：
  名称：

  ipso-and para-Functionalization of meta-terphenyl ligands with substituted methyl groups: Unusual head-to-tail coupling of terphenyl moieties

  摘要：

  The synthesis and characterization of several ipso-functionalized derivatives of the bulky terphenyl group C6H3-2,6(C6H3-2',6'-Pr-2(i))(2)(Ar') are described. These include the primary alcohol Ar'CH2OH (1), the bromo derivative Ar'CH2Br (2), and the terphenyl formate Ar'CH2OC(O)H (3). The alcohol 1 was obtained by treatment of LiAr' with formaldehyde, and 1 was readily converted to the bromo derivative 2 using HBr. The reaction of 1 with formic acid afforded 3 in good yield. Attempts to form the Grignard derivative of 1, i.e., Ar'CH2MgBr, resulted in a head-to-tail reaction of the terphenyl benzyl units to yield an unusual coupled product 4. An approach to the avoidance of this coupling involved the synthesis of the terphenyl derivatives 1-I-C6H2-2,6(C6H3-2',6'-Pr-2(i))(2)-4-Me (5) and 1-I-C6H2-2,6(C6H2-2',4',6'-Pr-3(i))(2)-4-Me (6), bearing methyl groups in the para positions of the central aryl ring, which could be prepared in good yield, and converted to their respective lithium salts 7 and 8 without complication. The compounds were characterized by H-1 and C-13 NMR spectroscopy, IR spectroscopy (1) and X-ray crystallography (2, 4, 5 and 6). (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.01.047
• 作为产物：
  描述：

  1,3-二氯-2-碘苯 在 lithium aluminium tetrahydride 、 正丁基锂 、 magnesium 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 39.0h， 生成 2,6-bis(2,6-diisopropylphenyl)benzyl alcohol
  参考文献：
  名称：

  Concave Reagents. New 2'-Substituted m-Terphenyls

  摘要：

  新的2'-取代的2,2'',6,6''-四甲基-1,1':3',1''-联苯已经合成。凹面酸4b-6b的溶解度可以通过在4和4''位置进行取代而增强，从而允许研究氢键异二聚体。凹面酸对2-氨基吡啶7显示出比非大环化合物更大的结合常数，可能是由于大环屏蔽阻止了同二聚体形成。新的2,6-二芳基苄醇1d、8d和9d已经合成并在质子化反应中进行了测试。新的官能团被引入到2'位置：OH（酚1f和12f）和NH₂（苯胺1j）。苯胺1j在乙醇中的碱性通过滴定法确定，并与其他碱进行了比较。此外，磺酸1l和17l已经制备，并且相应的甲酯1m和17m作为甲基化试剂进行了测试。

  DOI：

  10.1135/cccc20041325

文献信息

• Concave Reagents. New 2'-Substituted m-Terphenyls
  作者：Michael Abbass、Christine Kühl、Christian Manthey、Anja Müller、Ulrich Lüning

  DOI：10.1135/cccc20041325

  日期：——

  New 2'-substituted 2,2'',6,6''-tetramethyl-1,1':3',1''-terphenyls have been synthesized. Solubility of concave acids 4b-6b could be enhanced by substitution in 4 and 4'' position, allowing the study of hydrogen-bonded heterodimers. Concave acids show larger binding constants for 2-amidopyridines 7 than non-macrocyclic ones, probably due to the prevention of homodimer formation by the macrocyclic shielding. New 2,6-diarylbenzyl alcohols 1d, 8d and 9d have been synthesized and tested in protonation reactions. New functional groups were introduced into the 2' position: OH (phenols 1f and 12f) and NH₂ (aniline 1j). The basicity of aniline 1j in ethanol was determined by titration and was compared to other bases. Also sulfonic acids 1l and 17l were prepared, and the corresponding methyl esters 1m and 17m were tested as methylating agents.

  新的2'-取代的2,2'',6,6''-四甲基-1,1':3',1''-联苯已经合成。凹面酸4b-6b的溶解度可以通过在4和4''位置进行取代而增强，从而允许研究氢键异二聚体。凹面酸对2-氨基吡啶7显示出比非大环化合物更大的结合常数，可能是由于大环屏蔽阻止了同二聚体形成。新的2,6-二芳基苄醇1d、8d和9d已经合成并在质子化反应中进行了测试。新的官能团被引入到2'位置：OH（酚1f和12f）和NH₂（苯胺1j）。苯胺1j在乙醇中的碱性通过滴定法确定，并与其他碱进行了比较。此外，磺酸1l和17l已经制备，并且相应的甲酯1m和17m作为甲基化试剂进行了测试。
• ipso-and para-Functionalization of meta-terphenyl ligands with substituted methyl groups: Unusual head-to-tail coupling of terphenyl moieties
  作者：Corneliu Stanciu、Alexander R. Fox、Anne F. Richards、James C. Fettinger、Philip P. Power

  DOI：10.1016/j.jorganchem.2006.01.047

  日期：2006.5

  The synthesis and characterization of several ipso-functionalized derivatives of the bulky terphenyl group C6H3-2,6(C6H3-2',6'-Pr-2(i))(2)(Ar') are described. These include the primary alcohol Ar'CH2OH (1), the bromo derivative Ar'CH2Br (2), and the terphenyl formate Ar'CH2OC(O)H (3). The alcohol 1 was obtained by treatment of LiAr' with formaldehyde, and 1 was readily converted to the bromo derivative 2 using HBr. The reaction of 1 with formic acid afforded 3 in good yield. Attempts to form the Grignard derivative of 1, i.e., Ar'CH2MgBr, resulted in a head-to-tail reaction of the terphenyl benzyl units to yield an unusual coupled product 4. An approach to the avoidance of this coupling involved the synthesis of the terphenyl derivatives 1-I-C6H2-2,6(C6H3-2',6'-Pr-2(i))(2)-4-Me (5) and 1-I-C6H2-2,6(C6H2-2',4',6'-Pr-3(i))(2)-4-Me (6), bearing methyl groups in the para positions of the central aryl ring, which could be prepared in good yield, and converted to their respective lithium salts 7 and 8 without complication. The compounds were characterized by H-1 and C-13 NMR spectroscopy, IR spectroscopy (1) and X-ray crystallography (2, 4, 5 and 6). (c) 2006 Elsevier B.V. All rights reserved.