rac-2-(3-methoxy-4-methylphenyl)propan-1-ol | 1111235-67-6

• 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: rac-2-(3-methoxy-4-methylphenyl)propan-1-ol
• 英文别名: 2-(3-methoxy-4-methylphenyl)propan-1-ol
• CAS: 1111235-67-6
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: FYBQFZVCPHEDDM-UHFFFAOYSA-N

物化性质

• 沸点：
  275.0±28.0 °C(Predicted)
• 密度：
  1.016±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  rac-2-(3-methoxy-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 21.0h， 生成
  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：

  2-甲氧基-1-甲基-4-丙-1-烯-2-基苯 在 dimethyl sulfide borane 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以85%的产率得到rac-2-(3-methoxy-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

• Two-step Biocatalytic Resolution of rac-Primary Alcohol for Obtaining Each Isomeric Intermediate of Xanthorrhizol
  作者：Jung In Pyo、Ryung Wha Kim、Azam Sharif Mohammed Shafioul、Chiman Song、Chan Seong Cheong、Kwan Soo Kim

  DOI：10.5012/bkcs.2013.34.1.252

  日期：2013.1.20

  these reports, there is no one which gave both enantiomers as a pure state. Thus, we focused on the development of a method obtaining both enantiomers using a biocatalyst. As reported previously in patent, the primary alcohol 2, 2-(3-methoxy-4-methylphenyl)propan-1ol, was selected as a substrate for resolution as Figure 1. In order to prepare it, the commercially available compound 3, methyl 3-methoxy-3-methyl

  从多种天然产品中提取出有益于人类健康的有趣化合物，并表现出各种生物活性，如抗癌、抗真菌、抗氧化等。它们已被用作原料混合物或改性单一成分以提高功效。此外，天然产物已被用作新药发现计划的先导化合物。酚类倍半萜类化合物因其广泛的生物活性而备受关注。其中，黄根醇已被研究用于寻找新的生物活性。它首先由 Kochendoerfer 从 Curcuma xanthorrhiza Roxb 的根茎中分离出来。并表现出抗菌和抗真菌活性。它有一个手性中心，因此可以生成 (R) 和 (S)-异构体，如图 1 所示。(R)-xanthorrhizol 显示出抗菌活性，它是一种天然存在的异构体。由于其广泛的药理活性，一些研究小组已将其合成为外消旋体或对映体纯化合物。其中，3-甲氧基-4-甲基苯乙酮用作原料并与相应的高戊二烯溴反应。迈耶斯等人。不对称合成的 (S)-xanthorrhizol 和使用恶唑啉作为手性助剂
• Lipase Catalyzed Kinetic Resolution of rac-2-(3-Methoxy-4-methylphenyl) propan-1-ol and rac-2-(3-Hydroxy-4-methylphenyl)propyl propanoate for S-(+)-Xanthorrhizol
  作者：Azam Sharif Mohammed Shafioul、Chan-Seong Cheong

  DOI：10.5012/bkcs.2012.33.2.409

  日期：2012.2.20

  R-(+)-2-(3-methoxy-4-methylphenyl) propan-1-ol resolution processes were developed via lipase-catalyzed reaction. Wefound lipase Aspergillus oryzae (AOL) and Porcine pancreas (PPL) are selective to transesterification andhydrolysis in organic and aqueous phase. Modified demethylated substrate is appropriate for enantioselectivehydrolysis reaction without any additives. Enantiopure chiral alcohol was crystallized from

  黄柏酚是一种双羟基天然倍半萜，是莪术精油的主要成分。2-(3-甲氧基-4-甲基苯基)丙-1-醇和 2-(3-羟基-4-甲基苯基)丙-1-醇可能是对映体选择性合成黄柏酚的基本成分。通过脂肪酶催化反应，开发了R-(+)-2-(3-羟基-4-甲基苯基)丙-1-醇的对映体选择性（c = 53%，E = $80\pm}3$）和R-(+)-2-(3-甲氧基-4-甲基苯基)丙-1-醇的对映体选择性（c = 58%，E = $27\pm}1$）解析过程。我们发现脂肪酶 Aspergillus oryzae (AOL) 和猪胰腺 (PPL) 在有机相和水相中对酯交换反应和水解具有选择性。改良的去甲基化底物适用于不含任何添加剂的对映体选择性水解反应。对映体纯手性乙醇从乙酸乙酯/正己烷共溶剂系统中结晶出来。克尺度解析的手性中间体将促进非天然 S-(+)-xanthorrhizol 的合成，它是天然 S-(+)-xanthorrhizol 的相应异构体。
• Lipase catalyzed kinetic resolution of rac-2-phenylpropan-1-ol derivatives as building block for phenolic sesquiterpenes
  作者：Azam Sharif Mohammed Shafioul、Chan Seong Cheong

  DOI：10.1016/j.molcatb.2011.10.005

  日期：2012.2

  Highly enantioselective and enantiospecific resolution processes were developed for 2-(3-methoxy-4-methyl-phenyl)-propan-1-ol (VI), 2-(2-methoxy-5-methyl-phenyl)-propan-1-ol (VII), 2-(3,4,5-trimethoxy-phenyl)-propan-1-ol (VIII) and 2-(3-hydroxy-4-methyl-phenyl)-propan-1-ol (XII) via lipase-catalyzed transesterification and hydrolysis using vinyl propionate as acylating agent. The general procedure for synthesis and kinetic resolution of 2-phenylpropan-1-ol derivatives would be beneficial for getting chiral building block of bisabolane types of natural and unnatural sesquiterpenes. Gallic acid moiety was diversified with a chiral center at the benzylic position and subsequent resolution process gave resolved isomers with higher enantiopurity. Both isomers were separated with ee of at least 95%. Enantioselectivity, E was even higher up to 316 during the process. These resolved chiral intermediates will facilitate the commercial synthesis of bio-active natural and unnatural xanthorrhizol, elvirol and gallate derivatives. (C) 2011 Elsevier B.V. All rights reserved.