(S)-2-(3-methoxy-4-methylphenyl)propan-1-ol | 220728-54-1

• 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-(3-methoxy-4-methylphenyl)propan-1-ol
• 英文别名: (2S)-2-(3-methoxy-4-methylphenyl)propan-1-ol
• CAS: 220728-54-1
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: FYBQFZVCPHEDDM-SECBINFHSA-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：

  (S)-2-(3-methoxy-4-methylphenyl)propan-1-ol 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以87%的产率得到(S)-4-(1-bromopropan-2-yl)-2-methoxy-1-methylbenzene
  参考文献：
  名称：

  外消旋α-溴代酯与芳基锌的钴催化对映选择性Negishi交叉偶联

  摘要：

  公开了第一个钴催化的对映选择性Negishi交叉偶联反应，以及α-卤代酯与芳基卤化锌的第一个芳基化反应。使用钴-二恶唑啉钴催化剂，可以以优异的对映选择性和高收率（高达97％ee和98％收率）合成各种α-芳基链烷酸酯 。该方法可耐受各种官能团，包括醚，卤化物，硫醚，甲硅烷基，胺，酯，乙缩醛，酰胺，烯烃和杂芳族化合物。该方法适用于克级反应，可合成高纯度的（R）-花草苷。自由基时钟实验支持自由基的中介作用。

  DOI：

  10.1002/chem.201705463
• 作为产物：
  描述：

  rac-2-(3-methoxy-4-methylphenyl)propan-1-ol 在 Aspergillus oryzae lipase 作用下， 以 aq. phosphate buffer 、 丙酮 为溶剂， 反应 9.0h， 生成 (S)-2-(3-methoxy-4-methylphenyl)propan-1-ol
  参考文献：
  名称：

  外消旋伯醇两步生物催化拆分获得黄根醇异构体中间体

  摘要：

  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

  DOI：

  10.5012/bkcs.2013.34.1.252

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.
• 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.
• An Enantiocontrolled Total Synthesis of (-)-Xanthorrhizol
  作者：Kozo Shishido、Kenji Sato、Toshikazu Bando、Mitsuru Shindo

  DOI：10.3987/com-98-s(h)4

  日期：——
• Cobalt‐Catalyzed Enantioselective Negishi Cross‐Coupling of Racemic α‐Bromo Esters with Arylzincs
  作者：Feipeng Liu、Jiangchun Zhong、Yun Zhou、Zidong Gao、Patrick J. Walsh、Xueyang Wang、Sijie Ma、Shicong Hou、Shangzhong Liu、Minan Wang、Min Wang、Qinghua Bian

  DOI：10.1002/chem.201705463

  日期：2018.2.9

  enantioselective Negishi cross‐coupling reaction, and the first arylation of α‐halo esters with arylzinc halides, are disclosed. Employing a cobalt‐bisoxazoline catalyst, various α‐arylalkanoic esters were synthesized in excellent enantioselectivities and yields (up to 97 % ee and 98 % yield). A diverse range of functional groups, including ether, halide, thioether, silyl, amine, ester, acetal, amide, olefin

  公开了第一个钴催化的对映选择性Negishi交叉偶联反应，以及α-卤代酯与芳基卤化锌的第一个芳基化反应。使用钴-二恶唑啉钴催化剂，可以以优异的对映选择性和高收率（高达97％ee和98％收率）合成各种α-芳基链烷酸酯 。该方法可耐受各种官能团，包括醚，卤化物，硫醚，甲硅烷基，胺，酯，乙缩醛，酰胺，烯烃和杂芳族化合物。该方法适用于克级反应，可合成高纯度的（R）-花草苷。自由基时钟实验支持自由基的中介作用。
• 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