2-(2,5-dimethoxy-4-methylphenyl)propan-1-ol | 38844-21-2

• 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: 2-(2,5-dimethoxy-4-methylphenyl)propan-1-ol
• 英文别名: 2,5-Dimethoxy-β,4-dimethylphenetylalkohol；2-(2,5-Dimethoxy-4-methylphenyl)propan-1-ol
• CAS: 38844-21-2
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: BWWNPJOYCYOYMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 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：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2,5-dimethoxy-4-methylphenyl)propan-1-ol 在 吡啶 、 甲醇 、 Porcine pancreas lipase type II 、 sodium hydroxide 作用下， 以 甲基叔丁基醚 、 二甲基亚砜 为溶剂， 反应 8.0h， 生成 (3R)-3-(2,5-dimethoxy-4-methylphenyl)butanenitrile
  参考文献：
  名称：

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

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2011.03.012
• 作为产物：
  描述：

  1-(2,5-二甲氧基-4-甲基苯基)乙酮 在 dimethyl sulfide borane 、 对甲苯磺酸 、 对苯二酚 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 6.5h， 生成 2-(2,5-dimethoxy-4-methylphenyl)propan-1-ol
  参考文献：
  名称：

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

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2011.03.012

文献信息

• Nakao,H. et al., Chemical and pharmaceutical bulletin, 1972, vol. 20, p. 1968 - 1979
  作者：Nakao,H. et al.

  DOI：——

  日期：——
• Asymmetric syntheses of heliannuols B and D
  作者：Jiyong Zhang、Xiaolei Wang、Wenkuan Wang、Weiguo Quan、Xuegong She、Xinfu Pan

  DOI：10.1016/j.tet.2007.05.034

  日期：2007.7

  The synthesis of heliannuol D along with the first synthesis of heliannuol B has been achieved using Mitsunobu reaction and ring-closing metathesis as the key steps. (C) Elsevier Ltd. All rights reserved.
• 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.