2-(2-bromophenyl)propan-1-ol | 34868-16-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-bromophenyl)propan-1-ol
• CAS: 34868-16-1
• 化学式: C₉H₁₁BrO
• 分子量: 215.09
• InChiKey: FNEYKDACFQTJTH-UHFFFAOYSA-N

物化性质

• 沸点：
  273.6±15.0 °C(Predicted)
• 密度：
  1.404±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2-bromophenyl)propan-1-ol 在 Pseudomonas cepacia lipase 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 甲基叔丁基醚 为溶剂， 生成 (R)-(+)-2-苯基-1-丙醇
  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-(2-溴苯基)-2-丙醇 在 dimethyl sulfide borane 、 对甲苯磺酸 、 对苯二酚 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 3.0h， 生成 2-(2-bromophenyl)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

• [EN] BORON-CONTAINING SMALL MOLECULES AS ANTI-PROTOZOAL AGENT<br/>[FR] PETITES MOLÉCULES BORÉES EN TANT QU'AGENT ANTI-PROTOZOAIRE
  申请人：ANACOR PHARMACEUTICALS INC

  公开号：WO2011116348A1

  公开（公告）日：2011-09-22

  This invention provides, among other things, novel compounds useful for treating protozoal infections, pharmaceutical compositions containing such compounds, as well as combinations of these compounds with at least one additional therapeutically effective agent. The compounds are of the formula, wherein Y' is a halogen, Y is halosubstituted alkyl, or a salt thereof.

  这项发明提供了用于治疗原虫感染的新型化合物，含有这些化合物的药物组合物，以及这些化合物与至少一种额外治疗有效药剂的组合物。这些化合物的化学式为，其中Y'是卤素，Y是卤代烷基，或其盐。
• Synthesis of Alcohols via a Rhodium-Catalyzed Hydroformylation- Reduction Sequence using Tertiary Bidentate Amine Ligands
  作者：Lawrence L. W. Cheung、Giuseppe Vasapollo、Howard Alper

  DOI：10.1002/adsc.201200053

  日期：2012.7.9

  The synthesis of alcohols from aromatic olefins is described using a rhodium‐catalyzed hydroformylation–reduction sequence with the assistance of a tertiary diamine ligand. The alcohols are produced in excellent branched to linear ratios and in good to excellent isolated yields. In all cases no aldehyde product, from hydroformylation, or alkyl product, from olefin reduction, was detected.

  描述了在叔二胺配体的帮助下，使用铑催化的加氢甲酰化-还原序列，由芳族烯烃合成醇。这些醇以极佳的支链与线性比率以及极佳的极佳分离收率生产。在所有情况下，均未检测到加氢甲酰化产生的醛产物或烯烃还原产生的烷基产物。
• Highly efficient NHC-iridium-catalyzed β-methylation of alcohols with methanol at low catalyst loadings
  作者：Zeye Lu、Qingshu Zheng、Guangkuo Zeng、Yunyan Kuang、James H. Clark、Tao Tu

  DOI：10.1007/s11426-021-1017-0

  日期：2021.8

  and secondary alcohols with methanol has been achieved by using bis-N-heterocyclic carbene iridium (bis-NHC-Ir) complexes. Broad substrate scope and up to quantitative yields were achieved at low catalyst loadings with only hydrogen and water as by-products. The protocol was readily extended to the β-alkylation of alcohols with several primary alcohols. Control experiments, along with DFT calculations

  醇的甲基化非常重要，因为大量的生物活性和药用醇都含有甲基。在这里，通过使用双-N-杂环卡宾铱（双-NHC-Ir）配合物实现了伯醇和仲醇与甲醇的高效β-甲基化。在仅氢和水作为副产物的低催化剂负载下实现了广泛的底物范围和高达定量的产率。该协议很容易扩展到β- 醇与几种伯醇的烷基化。对照实验以及 DFT 计算和晶体学研究表明，配体效应对其优异的催化性能至关重要，为与简单醇进行更具挑战性的格尔伯特反应提供了线索。
• Cascade intramolecular Prins/Friedel–Crafts cyclization for the synthesis of 4-aryltetralin-2-ols and 5-aryltetrahydro-5<i>H</i>-benzo[7]annulen-7-ols
  作者：Jie Zheng、Shuyu Meng、Quanrui Wang

  DOI：10.3762/bjoc.17.104

  日期：——

  The treatment of 2-(2-vinylphenyl)acetaldehydes or 3-(2-vinylphenyl)propanals with BF3·Et2O results in an intramolecular Prins reaction affording intermediary benzyl carbenium ions, which are then trapped by a variety of electron-rich aromatics via Friedel–Crafts alkylation. This cascade Prins/Friedel–Crafts cyclization protocol paves an expedient path to medicinally useful 4-aryltetralin-2-ol and

  用 BF 3 ·Et 2 O处理 2-(2-乙烯基苯基) 乙醛或 3-(2-乙烯基苯基) 丙醛导致分子内 Prins 反应，提供中间的苄基碳正离子，然后被各种富电子捕获芳烃通过 Friedel-Crafts 烷基化。这种级联 Prins/Friedel-Crafts 环化方案为获得具有药用价值的 4-aryltetralin-2-ol 和 5-aryltetrahydro-5 H - benzo[7]annulen-7-ol 衍生物铺平了道路。
• Iron-Catalyzed β-Alkylation of Alcohols
  作者：Léo Bettoni、Sylvain Gaillard、Jean-Luc Renaud

  DOI：10.1021/acs.orglett.9b03171

  日期：2019.10.18

  alkylated alcohols have been prepared in good yields using a double-hydrogen autotransfer strategy in the presence of our diaminocyclopentadienone iron tricarbonyl complex Fe1. The alkylation of some 2-arylethanol derivatives was successfully addressed with benzylic alcohols and methanol as alkylating reagents under mild conditions. Deuterium labeling experiments suggested that both alcohols (2-arylethanol

  在我们的二氨基环戊二烯酮铁三羰基络合物Fe1存在下，使用双氢自动转移策略以高收率制备了β-支化烷基化醇。在温和条件下，用苄醇和甲醇作为烷基化试剂成功地解决了一些2-芳基乙醇衍生物的烷基化问题。氘标记实验表明，在该级联过程中，两种醇（2-芳基乙醇和甲醇或苄醇）均用作氢供体。