2,2,4,4-Tetramethyl-3-naphthalen-1-ylpentan-3-ol | 189141-53-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2,4,4-Tetramethyl-3-naphthalen-1-ylpentan-3-ol
• 英文别名: 2,2,4,4-tetramethyl-3-naphthalen-1-ylpentan-3-ol
• CAS: 189141-53-5；189173-50-0；210573-15-2
• 化学式: C₁₉H₂₆O
• 分子量: 270.415
• InChiKey: VLQBSTPNRQYQPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  2,2,4,4-Tetramethyl-3-naphthalen-1-ylpentan-3-ol 、 碘甲烷 在 potassium hydride 作用下， 生成 2,2,4,4-tetramethyl-3-(α-naphthyl)-3-methoxypentane
  参考文献：
  名称：

  Conformational Studies by Dynamic NMR. 64.¹ Stereomutations of Atropisomers and of Conformational Enantiomers in Ethers of Hindered Naphthylcarbinols

  摘要：

  Methyl or ethyl ethers of 1-naphthyl carbinols ArCR2OR' (Ar = 1-naphthyl, R' = Me, Et) can occur in a range of rotational conformations whose population varies with the nature of the substituents R. The passage between such conformation minima is achieved by rotation, during which one group R or OR' passes either the 2- or the 8-position of the naphthalene, and depending on the nature of R and OR', some of these interconversions are slow on the NMR time scale. Dynamic NMR experiments, supported by molecular mechanics calculations, show that different minima are preferred as the R group changes. These conformations are identified, their populations are determined, and the barriers to their interconversions are measured. In particular when R is a tert-butyl group, two atropisomers (with the OMe moiety near the 2- or 8-position) could be physically separated and their structures determined by NOE experiments in solution and X-ray diffraction in the solid state. Each of these exists as a pair of stereolabile enantiomers, with a barrier of 9-10 kcal mol(-1) for interconversion.

  DOI：

  10.1021/jo9804801
• 作为产物：
  描述：

  2,2,4,4-四甲基-3-戊酮 、 naphthalen-1-yl-lithium 以 四氢呋喃 为溶剂， 生成 2,2,4,4-Tetramethyl-3-naphthalen-1-ylpentan-3-ol
  参考文献：
  名称：

  动态核磁共振的构象研究。59.（1）受阻萘甲醇的阻转异构体中构象对映异构体的立体动力学。

  摘要：

  萘二烷基甲醇ArRR'COH（Ar = 1-萘基或1-萘基-2-甲基）以一对阻转异构体的形式存在，这些阻转异构体是由围绕Ar-COH键的受限旋转产生的。它们可以通过低温NMR光谱进行检测，但是如果两个烷基取代基均为大的叔丁基，则它们也可以在室温下作为稳定的化合物分离（一个这样的例子由化合物1提供，R = R'= Bu（t ），其中Ar = 1-萘基）。发现这些阻转异构体相互转化的活化自由能（DeltaG（））在7.6 kcal mol（-）（1）之间变化（如7中，R = R'= Me，Ar = 1-萘基-2-甲基）和32.9 kcal mol（-）（1）（与1相同）。通过差值NOE实验或利用在两种阻转异构体中相差很大的H-8化学位移来分配正周平面（sp）或反周平面（ap）结构。取决于取代基，在平衡处更稳定的物质可以是sp或ap阻转异构体。当R = R'= Pr（i）且R = R'= Et（如果Ar

  DOI：

  10.1021/jo970113+

文献信息

• Conformational Studies by Dynamic Nuclear Magnetic Resonance. 59.¹ Stereodynamics of Conformational Enantiomers in the Atropisomers of Hindered Naphthylcarbinols
  作者：Daniele Casarini、Lodovico Lunazzi、Andrea Mazzanti

  DOI：10.1021/jo970113+

  日期：1997.5.1

  Naphthyldialkylmethanols ArRR'COH (Ar = 1-naphthyl or 1-naphthyl-2-methyl) exist as a pair of atropisomers created by the restricted rotation about the Ar-COH bond. They can be detected by low-temperature NMR spectroscopy but can also be separated as stable compounds at room temperature if both the alkyl substituents are bulky tert-butyl groups (one such example is provided by compound 1, R = R' = Bu(t) with Ar = 1-naphthyl)

  萘二烷基甲醇ArRR'COH（Ar = 1-萘基或1-萘基-2-甲基）以一对阻转异构体的形式存在，这些阻转异构体是由围绕Ar-COH键的受限旋转产生的。它们可以通过低温NMR光谱进行检测，但是如果两个烷基取代基均为大的叔丁基，则它们也可以在室温下作为稳定的化合物分离（一个这样的例子由化合物1提供，R = R'= Bu（t ），其中Ar = 1-萘基）。发现这些阻转异构体相互转化的活化自由能（DeltaG（））在7.6 kcal mol（-）（1）之间变化（如7中，R = R'= Me，Ar = 1-萘基-2-甲基）和32.9 kcal mol（-）（1）（与1相同）。通过差值NOE实验或利用在两种阻转异构体中相差很大的H-8化学位移来分配正周平面（sp）或反周平面（ap）结构。取决于取代基，在平衡处更稳定的物质可以是sp或ap阻转异构体。当R = R'= Pr（i）且R = R'= Et（如果Ar
• Conformational Studies by Dynamic NMR. 64.¹ Stereomutations of Atropisomers and of Conformational Enantiomers in Ethers of Hindered Naphthylcarbinols
  作者：Daniele Casarini、Lodovico Lunazzi、Andrea Mazzanti、Elisabetta Foresti

  DOI：10.1021/jo9804801

  日期：1998.7.1

  Methyl or ethyl ethers of 1-naphthyl carbinols ArCR2OR' (Ar = 1-naphthyl, R' = Me, Et) can occur in a range of rotational conformations whose population varies with the nature of the substituents R. The passage between such conformation minima is achieved by rotation, during which one group R or OR' passes either the 2- or the 8-position of the naphthalene, and depending on the nature of R and OR', some of these interconversions are slow on the NMR time scale. Dynamic NMR experiments, supported by molecular mechanics calculations, show that different minima are preferred as the R group changes. These conformations are identified, their populations are determined, and the barriers to their interconversions are measured. In particular when R is a tert-butyl group, two atropisomers (with the OMe moiety near the 2- or 8-position) could be physically separated and their structures determined by NOE experiments in solution and X-ray diffraction in the solid state. Each of these exists as a pair of stereolabile enantiomers, with a barrier of 9-10 kcal mol(-1) for interconversion.