1-(9-anthryl)-tert-butyl carbinol | 162051-34-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-(9-anthryl)-tert-butyl carbinol
• 英文别名: (9-Anthryl)-tert-butylcarbinol；9-anthryl-tert-butylcarbinol；1-Anthracen-9-yl-2,2-dimethylpropan-1-ol；1-anthracen-9-yl-2,2-dimethylpropan-1-ol
• CAS: 162051-34-5
• 化学式: C₁₉H₂₀O
• 分子量: 264.367
• InChiKey: IOBSPCCFTXSJBJ-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：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  1-(9-anthryl)-tert-butyl carbinol 以 正己烷 、 异丙醇 为溶剂， 生成 (S)-9-anthryl-tert-butylcarbinol 、 (R)-9-anthryl-tert-butylcarbinol
  参考文献：
  名称：

  通过动力学拆分得到光学纯的大体积（杂）芳基烷基甲醇。

  摘要：

  平面手性亲核催化剂Fc-PIP用于动力学拆分庞大的（杂）芳基烷基甲醇，以对映体过量（> 99.0％ee）的未反应醇形式进行理想的转化，转化率为50.4-56.7％。

  DOI：

  10.1039/c1cc14591f
• 作为产物：
  描述：

  9-溴蒽 在 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 乙醚 为溶剂， 反应 5.33h， 生成 1-(9-anthryl)-tert-butyl carbinol
  参考文献：
  名称：

  Preparation of homochiral 9-anthryl-tert-butylcarbinol. The configurational and conformational NMR study of its carbamate derivatives

  摘要：

  The homochiral carbamates of 9-anthryl-tert-butylcarbinol were prepared and their conformational equilibrium was studied. The absolute configuration was determined by comparison of the NMR data with MM calculations. The enantiomers of the alcohol were obtained after chromatographic separation of carbamate derivatives and their hydrolysis. The same homochiral alcohols were prepared by direct chiral column chromatography.

  DOI：

  10.1016/0957-4166(95)00164-k

文献信息

• Crystal Structure and Stereoselective Solid-State Photodimerization of 1-(9-Anthryl)alkyl Acetates
  作者：Yukie Mori、Yumiko Horikoshi、Koko Maeda

  DOI：10.1246/bcsj.69.1755

  日期：1996.6

  X-Ray structure analyses of 1-(9-anthryl)alkyl acetates [AnCH(OAc)R; An = 9-anthryl, R = Me (1a), Et (1b), i-Pr (1c), t-Bu (1d), CF3 (1e)] indicated that these molecules adopted similar conformations in which the bond connecting the chiral carbon and the substituent was oriented almost perpendicular to the anthracene plane. In the crystals of 1b—1e two adjacent anthracenes related by an inversion center

  乙酸 1-(9-蒽基) 烷基酯 [AnCH(OAc)R; 的 X 射线结构分析；An = 9-anthryl, R = Me (1a), Et (1b), i-Pr (1c), t-Bu (1d), CF3 (1e)] 表明这些分子采用相似的构象，其中连接手性碳和取代基的取向几乎垂直于蒽平面。在 1b-1e 的晶体中，两个相邻的通过反转中心相关的蒽以较短的面间距（3.5-3.6 A）堆叠，这有利于形成中间头尾二聚体。1b、1c 和 1e 晶体的光解以几乎 100% 的产率提供了中间二聚体，而 1d 是光稳定的。1b (0.16) 的二聚化量子产率高于溶液中的量子产率。尽管二聚反应不是以单晶到单晶的方式进行，观察到的高选择性表明，即使单体的晶格被破坏，反应也会发生在 π 堆积对之间。苯溶液中的 1a-1e 辐照得到...
• Restricted Rotation and NOE Transfer: A Conformational Study of Some Substituted (9-Anthryl)carbinol Derivatives
  作者：Innocenzo de Riggi、Albert Virgili、Maria de Moragas、Carlos Jaime

  DOI：10.1021/jo00106a010

  日期：1995.1

  Four alkyl- and aryl(9-anthryl)carbinols (methyl, isopropyl, tert-butyl, and phenyl) were synthesized and revealed restricted rotation about the C-9-C-11 bond. Their free energy of activation for rotation has been determined, being 11.0, 14.0, 21.7, and 9.8 kcal/mol, respectively. The application of NOE enhancement and relaxation time measurements for the determination of the activation energy for bond rotation is described. The good agreement with the values obtained with the coalescence temperature method bears out that the NOE based approach is a good alternative for the determination of high rotational barriers. Molecular Mechanics (MM2) calculations give values close to the experimental ones.
• Mori, Yukie; Horikoshi, Yumiko; Maeda, Koko, Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1996, vol. 277, p. 39 - 44
  作者：Mori, Yukie、Horikoshi, Yumiko、Maeda, Koko

  DOI：——

  日期：——
• Optically pure bulky (hetero)arylalkyl carbinols via kinetic resolution
  作者：Bin Hu、Meng Meng、John S. Fossey、Weimin Mo、Xinquan Hu、Wei-Ping Deng

  DOI：10.1039/c1cc14591f

  日期：——

  Planar chiral nucleophilic catalyst Fc-PIP was employed in the kinetic resolution of bulky (hetero)arylalkyl carbinols delivering unreacted alcohols with extremely high enantiomeric excess (>99.0% ees) in ideal conversions ranging from 50.4-56.7%.

  平面手性亲核催化剂Fc-PIP用于动力学拆分庞大的（杂）芳基烷基甲醇，以对映体过量（> 99.0％ee）的未反应醇形式进行理想的转化，转化率为50.4-56.7％。
• Preparation of homochiral 9-anthryl-tert-butylcarbinol. The configurational and conformational NMR study of its carbamate derivatives
  作者：Maria de Moragas、Adriana Port、Xavier Sánchez-Ruiz、Carlos Jaime、Christian Roussel、Albert Virgili

  DOI：10.1016/0957-4166(95)00164-k

  日期：1995.6

  The homochiral carbamates of 9-anthryl-tert-butylcarbinol were prepared and their conformational equilibrium was studied. The absolute configuration was determined by comparison of the NMR data with MM calculations. The enantiomers of the alcohol were obtained after chromatographic separation of carbamate derivatives and their hydrolysis. The same homochiral alcohols were prepared by direct chiral column chromatography.