(R)-2-(1-hydroxyethyl)ethyl-5-methylanisole | 343266-74-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (R)-2-(1-hydroxyethyl)ethyl-5-methylanisole
• 英文别名: (R)-3-(2-methoxy-4-methylphenyl)-1-butanol；(R)-3-(2-methoxy-4-methylphenyl)butan-1-ol；(3R)-3-(2-methoxy-4-methylphenyl)butan-1-ol
• CAS: 343266-74-0
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: JXHRJPFKUMRZJH-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  对甲苯磺酰氯 、 (R)-2-(1-hydroxyethyl)ethyl-5-methylanisole 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (R)-3-(2-methoxy-4-methylphenyl)butyl 4-methyl-1-benzenesulfonate
  参考文献：
  名称：

  Enantioselective synthesis of (R)- and (S)-curcumene and curcuphenol: an efficient chemoenzymatic route

  摘要：

  An efficient enantioselective synthesis of curcumene and curcuphenol is described. The key intermediates, substituted butanoates 7a and 7b and their acids 8a and 8b are obtained in high enantiopurity (>99% eel by a lipase-catalyzed kinetic resolution process. The enantiopure intermediates thus obtained were utilized for the total synthesis of the target compounds. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.10.019
• 作为产物：
  描述：

  2,5-二甲基苯甲酸 在 正丁基锂 、 氯化亚砜 、 四甲基乙二胺 、 三氟过氧乙酸 、 仲丁基锂 、 potassium carbonate 、 臭氧 、 鹰爪豆碱 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 氯仿 、 环己烷 、 丙酮 、 正戊烷 为溶剂， 反应 29.58h， 生成 (R)-2-(1-hydroxyethyl)ethyl-5-methylanisole
  参考文献：
  名称：

  Novel Sparteine-Mediated Enantio-Dichotomic Formal Synthesis of (R)-(−)- and (S)-(+)-Curcuphenol

  摘要：

  High and opposite enantiodiscriminations were observed between tertiary amides and secondary amides in the sparteine-mediated lateral metalation-allylation of 2-ethyl-m-toluamide derivatives (2a, 2e), The results described above have been applied for the formal synthesis of both enantiomers of curcuphenol. The brief mechanistic studies suggested that stereoinformation was introduced after the deprotonation step.

  DOI：

  10.1021/jo001485c

文献信息

• Lipase-mediated resolution of substituted 2-aryl-propanols: application to the enantioselective synthesis of phenolic sesquiterpenes
  作者：Stefano Serra

  DOI：10.1016/j.tetasy.2011.03.012

  日期：2011.3

  A comprehensive study of the lipase-mediated resolution of substituted 2-aryl-propanols is reported. The latter alcohols were submitted to the irreversible acetylation catalyzed either by PPL, CRL, or lipase PS. The enantioselectivity of these transformations was dependent on the type of lipase used. The type of substituents and particularly their position on the aromatic ring strongly affected the selectivity of the reaction. The experiments described prove that PPL is the more versatile lipase catalyzing the acetylation with an enantiomeric ratio (E) value that ranges from 1 up to 144, depending on the substrate used. Conversely, the same transformations were catalyzed by CRL and lipase PS with an enantiomeric ratio value, which is always less than 5. The remarkable behavior of PPL was exploited in the large scale resolution of some substituted 2-aryl-propanols whose enantiomeric forms are relevant building blocks in the enantioselective synthesis of phenolic sesquiterpenes. By these means, the synthesis of (S)-turmeronol B and the formal syntheses of (R)-curcumene, (R)-curcuphenol, (R)-xanthorrhizol, and (R)-curcuhydroquinone were accomplished. (C) 2011 Elsevier Ltd. All rights reserved.