2-(2,6-di-tert-butylphenoxy)ethanol | 79618-25-0

• 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-(2,6-di-tert-butylphenoxy)ethanol
• 英文别名: 2-(2,6-di-t-butylphenoxy)ethanol；2-(2,6-Ditert-butylphenoxy)ethanol
• CAS: 79618-25-0
• 化学式: C₁₆H₂₆O₂
• 分子量: 250.381
• InChiKey: YQUMGFFVPAHLMT-UHFFFAOYSA-N

物化性质

• 沸点：
  125-127 °C(Press: 0.7 Torr)
• 密度：
  0.959±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2,6-di-tert-butylphenoxy)ethanol 在 一水合肼 、 三乙胺 作用下， 以 二氯甲烷 、 异丁醇 、 乙二醇甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.5h， 生成 (S)-2-[((2-(2,6-di-t-butylphenoxy)ethyl)amino)methyl]-1,4-benzodioxane
  参考文献：
  名称：

  QSAR study for a novel series of ortho disubstituted phenoxy analogues of α1-adrenoceptor antagonist WB4101

  摘要：

  On the basis of the affinities at the alpha(1a)-, alpha(1b)- and alpha(1d)-adrenoceptors and the 5-HT1A receptor of a previous series of sixteen 2-[(2-phenoxyethyl)aminomethyl]-1,4-benzodioxanes ortho monosubstituted at the phenoxy moiety, a number of ortho disubstituted analogues were designed, synthesized in both the enantiomeric forms and tested in binding assays on the same receptors. The affinity values of the new compounds 1-11 were compared with those of the enantiomers of the 2,6-dimethoxyphenoxy analogue, the well-known alpha 1 antagonist WB4101, and of the ortho monosubstituted derivatives, suggesting some distinctive aspects of the interaction of the phenoxy moiety, in particular with the alpha 1a-AR and the 5-HT1A receptor, of the monosubstituted and the disubstituted compounds. A classical quantitative structure-activity relationship (Hansch) analysis was applied to the whole set of the S enantiomers of the ortho mono- and disubstituted WB4101 analogues (26 compounds), finding a very good correlation for the a,, affinity. For this latter, a significant parabolic relationship was also found with the volume of the two ortho substituents. Diametrically opposite, the same relationships for the 5-HT1A exhibit low or insignificant correlation coefficients. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.04.004
• 作为产物：
  描述：

  2,6-二叔丁基苯酚 、 2-氯乙醇 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 0.17h， 以80%的产率得到2-(2,6-di-tert-butylphenoxy)ethanol
  参考文献：
  名称：

  Microwave Mediated Protection of Hindered Phenols and Alcohols

  摘要：

  在微波照射下，使用不同的烷基化试剂，在KOH/DMSO的存在下，将 hindered 酚和醇保护为其相应的醚。$$R-OH\;{KOH/DMSO,\;R^{\prime}-X,\;MW \\{\vec{10-15\;Mins,\;80%-90%\;Yield}}}\;R^{{/}^O{\backslash}}R^{\prime}$$.

  DOI：

  10.5012/jkcs.2012.56.6.706

文献信息

• Reaction of epoxides with 2,6-di-tert-butylphenol
  作者：Robert W. Layer

  DOI：10.1021/jo00338a037

  日期：1981.12
• LAYER, R. W., J. ORG. CHEM., 1981, 46, N 25, 5224-5225
  作者：LAYER, R. W.

  DOI：——

  日期：——
• XALIKOVA, N. U.;KRYSIN, A. P., IZV CO AN CCCP. CEP. XIM. N.,(1988) N 9/3, 95-101
  作者：XALIKOVA, N. U.、KRYSIN, A. P.

  DOI：——

  日期：——
• Microwave Mediated Protection of Hindered Phenols and Alcohols
  作者：Tejas Pothi、Mahesh Dawange、Kamlesh Chavan、Rajiv Sharma、Nabajyoti Deka

  DOI：10.5012/jkcs.2012.56.6.706

  日期：2012.12.20

  Hindered phenols and alcohols were protected as their corresponding ethers using different alkylating agents in presence of KOH/DMSO under microwave irradiation. $$R-OH\;KOH/DMSO,\;R^\prime}-X,\;MW \\\vec10-15\;Mins,\;80%-90%\;Yield}}}\;R^/}^O\backslash}}R^\prime}$$.

  在微波照射下，使用不同的烷基化试剂，在KOH/DMSO的存在下，将 hindered 酚和醇保护为其相应的醚。$$R-OH\;KOH/DMSO,\;R^\prime}-X,\;MW \\\vec10-15\;Mins,\;80%-90%\;Yield}}}\;R^/}^O\backslash}}R^\prime}$$.
• QSAR study for a novel series of ortho disubstituted phenoxy analogues of α1-adrenoceptor antagonist WB4101
  作者：M. Pallavicini、L. Fumagalli、M. Gobbi、C. Bolchi、S. Colleoni、B. Moroni、A. Pedretti、C. Rusconi、G. Vistoli、E. Valoti

  DOI：10.1016/j.ejmech.2006.04.004

  日期：2006.9

  On the basis of the affinities at the alpha(1a)-, alpha(1b)- and alpha(1d)-adrenoceptors and the 5-HT1A receptor of a previous series of sixteen 2-[(2-phenoxyethyl)aminomethyl]-1,4-benzodioxanes ortho monosubstituted at the phenoxy moiety, a number of ortho disubstituted analogues were designed, synthesized in both the enantiomeric forms and tested in binding assays on the same receptors. The affinity values of the new compounds 1-11 were compared with those of the enantiomers of the 2,6-dimethoxyphenoxy analogue, the well-known alpha 1 antagonist WB4101, and of the ortho monosubstituted derivatives, suggesting some distinctive aspects of the interaction of the phenoxy moiety, in particular with the alpha 1a-AR and the 5-HT1A receptor, of the monosubstituted and the disubstituted compounds. A classical quantitative structure-activity relationship (Hansch) analysis was applied to the whole set of the S enantiomers of the ortho mono- and disubstituted WB4101 analogues (26 compounds), finding a very good correlation for the a,, affinity. For this latter, a significant parabolic relationship was also found with the volume of the two ortho substituents. Diametrically opposite, the same relationships for the 5-HT1A exhibit low or insignificant correlation coefficients. (c) 2006 Elsevier SAS. All rights reserved.