(R)-2-methyl-1-(2,5-dimethylphenyl)propanol | 1163683-93-9

• 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: (R)-2-methyl-1-(2,5-dimethylphenyl)propanol
• 英文别名: (1R)-1-(2,5-dimethylphenyl)-2-methylpropan-1-ol
• CAS: 1163683-93-9
• 化学式: C₁₂H₁₈O
• 分子量: 178.274
• InChiKey: JTJZTXWESMBZAL-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-(2,5-dimethylphenyl)-2-methyl-propane-1-one 在 dimethyl sulfide borane 、 (S)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以95%的产率得到(R)-2-methyl-1-(2,5-dimethylphenyl)propanol
  参考文献：
  名称：

  Experimental transition state for the B-chlorodiisopinocampheylborane (DIP-Cl) reduction

  摘要：

  Asymmetric reductions of prochiral ketones are important transformations in the syntheses of natural products, pharmaceuticals, and fine chemicals. B-Chlorodiisopinocampheylborane (DIP-Cl), a stoichiometric reagent that is capable of reducing prochiral aralkyl ketones with high selectivity. Here, we utilize a recently developed C-13 kinetic isotope effect (KIE) methodology to probe the symmetry breaking process inherent to this asymmetric reduction. Experimental KIEs and computed transition structures indicate significant roles for non-bonding interaction, specific directed orbital interactions, and hydrogen tunneling in this reaction. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.216

文献信息

• Stereoselection in the Corey-Bakshi-Shibata Reduction: Insight from Kinetic Isotope Effects and Transition-Structure Modeling
  作者：Hui Zhu、Daniel J. O'Leary、Matthew P. Meyer

  DOI：10.1002/anie.201206011

  日期：2012.11.19

  demanding: Significant steric demand is isolated to the small (iPr) substituent in the oxazaborolidine‐catalyzed borane (CBS) reduction of 2′,5′‐dimethylisobutyrophenone. Computed transition‐structure models (see picture) demonstrate that nearly equivalent steric demand can be achieved from conformationally distinct transition structures.

  灵活但要求苛刻：在恶唑硼烷催化的硼烷（CBS）还原2'，5'-二甲基异丁苯酮中的小（i Pr）取代基上有很大的空间需求。计算的过渡结构模型（见图）表明，构象不同的过渡结构可以实现几乎相同的空间需求。
• Nonbonding Interactions and Stereoselection in the Corey−Bakshi−Shibata Reduction
  作者：Matthew P. Meyer

  DOI：10.1021/ol901707h

  日期：2009.10.1

  Deuterium kinetic isotope effect measurements upon enantiotopic methyl groups for the Corey-Bakshi-Shibata reduction of 2',5'-dimethylphenyl isopropyl ketone suggest a complex role for nonbonding interactions in the mediation of stereoselection.
• Experimental transition state for the B-chlorodiisopinocampheylborane (DIP-Cl) reduction
  作者：Sean E. Stafford、Matthew P. Meyer

  DOI：10.1016/j.tetlet.2009.03.216

  日期：2009.6

  Asymmetric reductions of prochiral ketones are important transformations in the syntheses of natural products, pharmaceuticals, and fine chemicals. B-Chlorodiisopinocampheylborane (DIP-Cl), a stoichiometric reagent that is capable of reducing prochiral aralkyl ketones with high selectivity. Here, we utilize a recently developed C-13 kinetic isotope effect (KIE) methodology to probe the symmetry breaking process inherent to this asymmetric reduction. Experimental KIEs and computed transition structures indicate significant roles for non-bonding interaction, specific directed orbital interactions, and hydrogen tunneling in this reaction. (C) 2009 Elsevier Ltd. All rights reserved.
• (R)-2-METHYL-(2,5-DIMETHYLPHENYL)PROPANOL AND (S)-(2-METHYL-2,5-DIMETHYLPHENYL)PROPANOL
  申请人：Meyer Matthew P.

  公开号：US20090163601A1

  公开（公告）日：2009-06-25

  This invention is directed to enantiomerically enriched (R)-2-methyl-(2,5-dimethylphenyl)propanol and (S)-2-methyl-(2,5-dimethylphenyl)propanol. The chiral alcohols are synthesized in enantiomerically enriched form by the reaction of 2-methyl-(2,5-dimethylphenyl)propanone using a chiral oxazaborolidine catalyst.
• Experimental transition state for the Corey–Bakshi–Shibata reduction
  作者：Jaime Saavedra、Sean E. Stafford、Matthew P. Meyer

  DOI：10.1016/j.tetlet.2009.01.033

  日期：2009.3

  Asymmetric reductions of prochiral ketones are important transformations in the syntheses of natural products, pharmaceuticals, and fine chemicals. The Corey-Bakshi-Shibata reduction is unique among hydride transfer reductions in its tremendous substrate range and catalytic nature. Here, a coordinated computational and experimental approach is taken toward understanding the origins of the high selectivity and broad Substrate range, which are hallmarks of this reduction. (C) 2009 Elsevier Ltd. All rights reserved.