(R)-1-(2,6-dimethylphenyl)ethanol

• 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)-1-(2,6-dimethylphenyl)ethanol
• 英文别名: (1R)-1-(2,6-dimethylphenyl)ethanol
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: BFLGMBBJIHKTAY-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  [(1R)-1-(2,6-dimethylphenyl)ethyl] acetate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.08h， 生成 (R)-1-(2,6-dimethylphenyl)ethanol
  参考文献：
  名称：

  Rapid, room-temperature acylative kinetic resolution of sec-alcohols using atropisomeric 4-aminopyridine/triphenylphosphine catalysis

  摘要：

  Two new atropisomeric 4-aminopyridine-based nucleophilic catalysts containing terphenyl 'blocking groups' have been prepared and evaluated for kinetic resolution (KR) of aryl alkyl sec-alcohols. One of these biaryls is shown to be the most selective atropisomeric catalyst yet prepared for several sec-alcohols but its low reactivity makes it non-optimal for use at room temperature (rt). Optimisation of the conditions for conducting KRs at rt using a previously described catalyst (containing a phenyl blocking group) at the 1 mol% level indicates that PPh3 (1 equiv) is beneficial for enantioselectivity and allows KR of (+/-)-1-(naphthyl)ethanol in less than 30 min with s > 15 (i.e. similar to 40% recovered alcohol with > 95% ee). These conditions constitute a convenient and practical method for rapid KR of sec-alcohols and are anticipated to facilitate a detailed kinetic study of this catalytic manifold by calorimetry. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.124

文献信息

• Axially Chiral Analogues of 4-(Dimethylamino)pyridine:  Novel Catalysts for Nonenzymatic Enantioselective Acylations
  作者：Alan C. Spivey、Tomasz Fekner、Sharon E. Spey

  DOI：10.1021/jo0000574

  日期：2000.5.1

  A concise seven-step synthesis of atropisomeric S-aryl analogues of DMAP from 4-pyridone 8 has been developed. A representative compound of this class, biaryl (+/-)-15, has been resolved using CSP HPLC and shown to be an efficient nucleophilic catalyst for kinetic resolution of a series of secondary alcohols on both an analytical and preparative scale (stereoselectivity factors, s = 8.9-29).
• Rapid, room-temperature acylative kinetic resolution of sec-alcohols using atropisomeric 4-aminopyridine/triphenylphosphine catalysis
  作者：Alan C. Spivey、Stellios Arseniyadis、Tomasz Fekner、Adrian Maddaford、David P. Leese

  DOI：10.1016/j.tet.2005.08.124

  日期：2006.1

  Two new atropisomeric 4-aminopyridine-based nucleophilic catalysts containing terphenyl 'blocking groups' have been prepared and evaluated for kinetic resolution (KR) of aryl alkyl sec-alcohols. One of these biaryls is shown to be the most selective atropisomeric catalyst yet prepared for several sec-alcohols but its low reactivity makes it non-optimal for use at room temperature (rt). Optimisation of the conditions for conducting KRs at rt using a previously described catalyst (containing a phenyl blocking group) at the 1 mol% level indicates that PPh3 (1 equiv) is beneficial for enantioselectivity and allows KR of (+/-)-1-(naphthyl)ethanol in less than 30 min with s > 15 (i.e. similar to 40% recovered alcohol with > 95% ee). These conditions constitute a convenient and practical method for rapid KR of sec-alcohols and are anticipated to facilitate a detailed kinetic study of this catalytic manifold by calorimetry. (c) 2005 Elsevier Ltd. All rights reserved.