(R)-1-([1,1-biphenyl]-3-yl)ethanol | 1225049-49-9

• 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: (R)-1-([1,1-biphenyl]-3-yl)ethanol
• 英文别名: 3-phenylacetophenol；(1R)-1-(3-phenylphenyl)ethanol
• CAS: 1225049-49-9
• 化学式: C₁₄H₁₄O
• 分子量: 198.265
• InChiKey: REAQEVBEEWTVLX-LLVKDONJSA-N

物化性质

• 沸点：
  348.0±21.0 °C(Predicted)
• 密度：
  1.067±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-乙酰基联苯 在 cobalt(II) acetate 、 bis-[2-((4S)-4-phenyl-4,5-dihydro-oxazol-2-yl)-phenyl]-amine 、 甲基二乙氧基硅烷 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到(R)-1-([1,1-biphenyl]-3-yl)ethanol
  参考文献：
  名称：

  铁和钴催化的双（恶唑啉基苯基）胺配体对酮和酮的不对称氢化硅烷化

  摘要：

  手性双（恶唑啉基苯基）胺被证明是铁和钴催化剂的有效辅助配体，对酮的不对称氢化硅烷化和烯酮的不对称共轭氢化硅烷化具有高活性。

  DOI：

  10.1002/chem.200903118

文献信息

• Iron- and Cobalt-Catalyzed Asymmetric Hydrosilylation of Ketones and Enones with Bis(oxazolinylphenyl)amine Ligands
  作者：Tomohiko Inagaki、Le Thanh Phong、Akihiro Furuta、Jun-ichi Ito、Hisao Nishiyama

  DOI：10.1002/chem.200903118

  日期：2010.3.8

  Chiral bis(oxazolinylphenyl)amines proved to be efficient auxiliary ligands for iron and cobalt catalysts with high activity for asymmetric hydrosilylation of ketones and asymmetric conjugate hydrosilylation of enones.

  手性双（恶唑啉基苯基）胺被证明是铁和钴催化剂的有效辅助配体，对酮的不对称氢化硅烷化和烯酮的不对称共轭氢化硅烷化具有高活性。
• Asymmetric Iron-Catalyzed Hydrosilane Reduction of Ketones: Effect of Zinc Metal upon the Absolute Configuration
  作者：Tomohiko Inagaki、Akihiro Ito、Jun-ichi Ito、Hisao Nishiyama

  DOI：10.1002/anie.201005363

  日期：2010.12.3

  Just a little bit: The 1/FeCl2 complex was activated in the presence of Zn and exhibited catalytic activity for the hydrosilane reduction of ketones to give the S‐configured alcohol. In contrast, the mixed‐catalyst system of 1 and Fe(OAc)2 provides the R enantiomer. This approach provides both enantiomers from a single chiral source by the addition of a small amount of Zn.

  一点点：1 / FeCl 2络合物在存在锌的情况下被激活，并表现出催化活性，可将酮的氢硅烷还原成S-构型醇。相反，1和Fe（OAc）2的混合催化剂体系提供R 对映体。该方法通过添加少量的Zn，从单一手性来源提供两种对映体。
• Novel Insights into the Combination of Metal‐ and Biocatalysis: Cascade One‐Pot Synthesis of Enantiomerically Pure Biaryl Alcohols in Deep Eutectic Solvents
  作者：Juraj Paris、Nicolás Ríos‐Lombardía、Francisco Morís、Harald Gröger、Javier González‐Sabín

  DOI：10.1002/cctc.201800768

  日期：2018.10.9

  concentration for the overall process. Moreover, both isolated enzymes and whole cells exhibited excellent activities which allowed to obtain a set of chiral biaryl alcohols in good yields and very high enantiomeric excess (>99 %).

  水中的化学酶联反应的开创性例子之一，例如钯催化的Suzuki-cross偶联，然后进行酶促还原，已经通过使用含有深共晶溶剂（DESs）的介质进行了催化性能的研究。因此，这些新型溶剂的独特性能使其能够在整个过程中达到较高的底物浓度。此外，分离的酶和全细胞均显示出优异的活性，这允许以良好的收率和非常高的对映体过量（> 99％）获得一组手性联芳基醇。
• An integrated immobilization strategy manipulates dual active centers to boost enantioselective tandem reactions
  作者：Xiaomin Shu、Ronghua Jin、Zhongrui Zhao、Tanyu Cheng、Guohua Liu

  DOI：10.1039/c8cc07841f

  日期：——

  Manipulation of dual active centers via an integrated immobilization strategy can overcome the restriction of homogeneous catalysis in a sequential organic transformation. Herein, by utilizing hollow-shell-structured silica, hydrogen-bonding immobilization via a ship-in-a-bottle synthesis locks a Pd(carbene) center in a nanocage and covalent-bonding immobilization tethers chiral Ru(diamine) centers

  通过集成的固定化策略操纵双重活性中心可以克服连续有机转化中均相催化的限制。在本文中，通过利用中空壳结构的二氧化硅，通过瓶装船合成进行氢键固定将纳米笼中的Pd（卡宾）中心和纳米通道内的共价键固定束缚手性Ru（二胺）中心锁定，构建杂双功能催化剂。这种双中心操作的好处是可以实现具有挑战性的Suzuki偶联-不对称转移氢化串联反应，该方法的优点是可以提供具有增强的反应性和对映选择性的各种手性联芳醇。
• Exploiting the enzymatic machinery of Arthrobacter atrocyaneus for oxidative kinetic resolution of secondary alcohols
  作者：Camila R. Silva、Juliana C. Souza、Lidiane S. Araújo、Edna Kagohara、Thaís P. Garcia、Vivian H. Pelizzari、Leandro H. Andrade

  DOI：10.1016/j.molcatb.2012.06.013

  日期：2012.11

  We evaluated Arthrobacter atrocyaneus (R1AF57) as producer of oxidoreductases for oxidative kinetic resolution of racemic secondary alcohols via oxidation reaction. This bacterium was isolated from Amazon soil samples using medium enriched with (RS)-1-(4-methylphenyl)ethanol as a carbon source. The kinetic resolution of several secondary alcohols through enantioselective oxidation mediated by resting cells and growing cells of A. atrocyaneus was efficiently achieved for the most alcohols. In general, it was possible to obtain only the (S)-enantiomer from (RS)-1-arylethanols. (C) 2012 Elsevier B.V. All rights reserved.