3-(2-isopropylphenyl)-2,2,4,4-tetramethylpentan-3-ol

• 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-(2-isopropylphenyl)-2,2,4,4-tetramethylpentan-3-ol
• 英文别名: 2,2,4,4-Tetramethyl-3-(2-propan-2-ylphenyl)pentan-3-ol
• 化学式: C₁₈H₃₀O
• 分子量: 262.436
• InChiKey: RFFAFNHNVWJGKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  3-(2-isopropylphenyl)-2,2,4,4-tetramethylpentan-3-ol 、 碘甲烷 在 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 以50%的产率得到1-(1-tert-butyl-1-methoxy-2,2-dimethyl-propyl)-2-isopropyl-benzene
  参考文献：
  名称：

  高度受阻的苄基醚的阻转异构体的结构，构型和立体动力学

  摘要：

  四种标题化合物的低温和NOE NMR光谱表明，与从头算的预测相一致，它们采用对折（sc）构象。在最受阻碍的导数（化合物4）的情况下，其构型是顺周平面（sp），这也可以通过X射线衍射看出。相应enantiomerization障碍，覆盖6.6至9.7千卡mol的范围内：此类stereolabile SP-或SC-阻转异构体作为两种对映异构体的构象存在- 1，可以为所有所检查的化合物进行测定。在两种情况下（化合物3和5），所述次要antiperiplanar（AP）阻转异构体也观察，并在sc向AP互屏障测量（11.7和11.9千卡摩尔-1）。另外，已经检测到异丙基和叔丁基取代基的旋转受限，并且已经确定了相应的屏障。

  DOI：

  10.1021/jo0603173
• 作为产物：
  描述：

  2,2,4,4-四甲基-3-戊酮 、 1-溴-2-异丙基苯 在 正丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 1.17h， 以44%的产率得到3-(2-isopropylphenyl)-2,2,4,4-tetramethylpentan-3-ol
  参考文献：
  名称：

  Stereolabile and Configurationally Stable Atropisomers of Hindered Aryl Carbinols

  摘要：

  Carbinols of the Ar-C(OH)R-2 type, Ar being o-isopropylphenyl, exist as stereolabile syn-clinal (sc) and anti-periplanar (ap) atropisomers when R = Me, Et, i-Pr. In the latter compound, the major atropisomer also comprises two enantiomeric forms that interchange with a barrier of 6.4 kcal mol(-1). X-ray diffraction, NOE experiments, and ab initio calculations indicate that the sc-atropisomer is the more stable form when R = Me, i-Pr, t-Bu but is the less stable one when R = Et. NMR spectra at variable temperature allowed the determination of the barriers for the interconversion of the sc- into the ap-atropisomers (Delta G(double dagger) = 7.6, 8.8, and 13.5 kcal mol(-1) for Me, Et, i-Pr, respectively). When R is a tert-butyl group, the two atropisomers are configurationally stable: the ap-atropisomer is obtained as the kinetic controlled compound, which can be transformed into the thermodynamically more stable sc-atropisomer with a free energy of activation of 29.3 kcal mol(-1). Both atropisomers exhibit restricted rotation of the tert-butyl moiety, the corresponding AG(double dagger) values being 9.4 and 8.8 kcal mol(-1) for the sc- and ap-atropisomer, respectively.

  DOI：

  10.1021/jo050382x

文献信息

• Stereolabile and Configurationally Stable Atropisomers of Hindered Aryl Carbinols
  作者：Daniele Casarini、Carmine Coluccini、Lodovico Lunazzi、Andrea Mazzanti

  DOI：10.1021/jo050382x

  日期：2005.6.1

  Carbinols of the Ar-C(OH)R-2 type, Ar being o-isopropylphenyl, exist as stereolabile syn-clinal (sc) and anti-periplanar (ap) atropisomers when R = Me, Et, i-Pr. In the latter compound, the major atropisomer also comprises two enantiomeric forms that interchange with a barrier of 6.4 kcal mol(-1). X-ray diffraction, NOE experiments, and ab initio calculations indicate that the sc-atropisomer is the more stable form when R = Me, i-Pr, t-Bu but is the less stable one when R = Et. NMR spectra at variable temperature allowed the determination of the barriers for the interconversion of the sc- into the ap-atropisomers (Delta G(double dagger) = 7.6, 8.8, and 13.5 kcal mol(-1) for Me, Et, i-Pr, respectively). When R is a tert-butyl group, the two atropisomers are configurationally stable: the ap-atropisomer is obtained as the kinetic controlled compound, which can be transformed into the thermodynamically more stable sc-atropisomer with a free energy of activation of 29.3 kcal mol(-1). Both atropisomers exhibit restricted rotation of the tert-butyl moiety, the corresponding AG(double dagger) values being 9.4 and 8.8 kcal mol(-1) for the sc- and ap-atropisomer, respectively.
• Structure, Conformation, and Stereodynamics of the Atropisomers of Highly Hindered Benzyl Ethers
  作者：Daniele Casarini、Carmine Coluccini、Lodovico Lunazzi、Andrea Mazzanti

  DOI：10.1021/jo0603173

  日期：2006.6.1

  the title compounds indicate that they adopt a synclinal (sc) conformation, in agreement with the prediction of ab initio computations. In the case of the most-hindered derivative (compound 4), the conformation is syn-periplanar (sp), as is also shown by X-ray diffraction. Such stereolabile sp- or sc-atropisomers exist as two conformational enantiomers: the corresponding enantiomerization barriers, covering

  四种标题化合物的低温和NOE NMR光谱表明，与从头算的预测相一致，它们采用对折（sc）构象。在最受阻碍的导数（化合物4）的情况下，其构型是顺周平面（sp），这也可以通过X射线衍射看出。相应enantiomerization障碍，覆盖6.6至9.7千卡mol的范围内：此类stereolabile SP-或SC-阻转异构体作为两种对映异构体的构象存在- 1，可以为所有所检查的化合物进行测定。在两种情况下（化合物3和5），所述次要antiperiplanar（AP）阻转异构体也观察，并在sc向AP互屏障测量（11.7和11.9千卡摩尔-1）。另外，已经检测到异丙基和叔丁基取代基的旋转受限，并且已经确定了相应的屏障。