(R)-2-(2,5-dimethoxy-4-methylphenyl)propan-1-ol | 289507-49-9

• 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-(2,5-dimethoxy-4-methylphenyl)propan-1-ol
• 英文别名: (2R)-2-(2,5-dimethoxy-4-methylphenyl)propan-1-ol
• CAS: 289507-49-9
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: BWWNPJOYCYOYMM-VIFPVBQESA-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：

  (R)-2-(2,5-dimethoxy-4-methylphenyl)propan-1-ol 在 吡啶 、 三丁基膦 、 potassium hydrogencarbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 (R)-1,4-dimethoxy-2-methyl-5-(1-(phenylsulfonyl)propan-2-yl)benzene
  参考文献：
  名称：

  Enantioselective total synthesis of heliannuols D and A †

  摘要：

  Heliannuols D和A表现出拮抗作用，首次通过碱介导的分子内环化合成，它们是通过苯酚环氧化物的手性选择性合成的，绝对结构通过全合成确立。

  DOI：

  10.1039/b003553j
• 作为产物：
  描述：

  (S)-2-(2,5-dimethoxy-4-methylphenyl)-3-hydroxypropyl acetate 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 (R)-2-(2,5-dimethoxy-4-methylphenyl)propan-1-ol
  参考文献：
  名称：

  Enantioselective total synthesis of heliannuols D and A †

  摘要：

  Heliannuols D和A表现出拮抗作用，首次通过碱介导的分子内环化合成，它们是通过苯酚环氧化物的手性选择性合成的，绝对结构通过全合成确立。

  DOI：

  10.1039/b003553j

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.
• Enantioselective total synthesis of heliannuols D and A †
  作者：Kenya Takabatake、Izumi Nishi、Mitsuru Shindo、Kozo Shishido

  DOI：10.1039/b003553j

  日期：——

  Heliannuols D and A, which exhibit allelopathic activity, were synthesized enantioselectively via a base-mediated intramolecular cyclisation of a phenolic epoxide for the first time, and the absolute structures were established by total synthesis.

  Heliannuols D和A表现出拮抗作用，首次通过碱介导的分子内环化合成，它们是通过苯酚环氧化物的手性选择性合成的，绝对结构通过全合成确立。
• Preparation and use of enantioenriched 2-aryl-propylsulfonylbenzene derivatives as valuable building blocks for the enantioselective synthesis of bisabolane sesquiterpenes
  作者：Stefano Serra

  DOI：10.1016/j.tetasy.2014.10.016

  日期：2014.12

  We have demonstrated that different enantioenriched 2-arylpropylsufonylbenzene derivatives are very useful building blocks for the synthesis of aromatic bisabolane sesquiterpenes. Their preparation and the exploitation of their chemical reactivity have been comprehensively investigated. Accordingly, the naturally occurring bisabolane sesquiterpenes (-)-curcuphenol, (-)-xanthorrhizol, (+)-glandulone A, (+)-curcudiol, (+)-turmerone and (+)-curcudiol-10-one were synthesized in high enantiomeric purity. It is worth noting that the compounds (+)-curcudiol-10-one and (+)-glandulone A were prepared in enantioenriched form for the first time. Through the proposed synthetic approaches, we were able to confirm both chemical structures and the absolute configurations previously assigned to the two aforementioned sesquiterpenes. (C) 2014 Elsevier Ltd. All rights reserved.