(S)-2-(2,5-dimethoxy-4-methylphenyl)propan-1-ol | 528606-13-5

• 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: (S)-2-(2,5-dimethoxy-4-methylphenyl)propan-1-ol
• 英文别名: (2S)-2-(2,5-dimethoxy-4-methylphenyl)propan-1-ol
• CAS: 528606-13-5
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: BWWNPJOYCYOYMM-SECBINFHSA-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：

  (S)-2-(2,5-dimethoxy-4-methylphenyl)propan-1-ol 在 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.67h， 生成 (S)-4-(2,5-Dimethoxy-4-methyl-phenyl)-pent-1-en-3-ol
  参考文献：
  名称：

  Enantioselective Syntheses of Heliannuols G and H

  摘要：

  DOI：

  10.3987/com-05-s(k)21
• 作为产物：
  描述：

  (S)-2-(2,5-dimethoxy-4-methylphenyl)-3-hydroxypropyl acetate 在 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 potassium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 (S)-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

• Enantioselective total synthesis of (–)-heliannuol A
  作者：Hidetoshi Kishuku、Mitsuru Shindo、Kozo Shishido

  DOI：10.1039/b211227b

  日期：2003.1.23

  An efficient and enantiocontrolled total synthesis of (-)-heliannuol A has been accomplished by employing ring closing metathesis and sequential diastereoselective epoxidation and regioselective reductive cleavage of the epoxide ring.

  （-）-helennuol A的有效和对映体控制的总合成已通过采用闭环易位，环氧化物环的连续非对映选择性环氧化和区域选择性还原性裂解来实现。
• 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 syntheses of the assigned structures of the helibisabonols A and B
  作者：Akari Miyawaki、Mayu Osaka、Makoto Kanematsu、Masahiro Yoshida、Kozo Shishido

  DOI：10.1016/j.tet.2011.03.064

  日期：2011.9

  The enantioselective syntheses of the compounds with the assigned structures of the helibisabonols A and B have been accomplished. Using an enzymatic desymmetrization of the sigma-symmetrical diol (route a) and a diastereoselective conjugate addition of the methyl to the enone with a chiral auxiliary (route b) we constructed the key tertiary stereogenic center at the benzylic position (C7) and then used an asymmetric dihydroxylation for assembling the C10 stereogenic center. In addition, possible diastereoisomers of the natural products were prepared and detailed comparisons of the H-1 and C-13 NMR spectra were conducted. As a result, the structure originally assigned to helibisabonol A may be revised to (7R,10R)-1. In the case of helibisabonol B, the (7R,10R)-2 would be reasonable based on a comparison of the NMR data and the biogenetic parallelism with helibisabonol A. (C) 2011 Elsevier Ltd. All rights reserved.