(R)-2-hydroxy-1-phenylethyl benzoate

• 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)-2-hydroxy-1-phenylethyl benzoate
• 英文别名: [(1R)-2-hydroxy-1-phenylethyl] benzoate
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: HEVQPHVLDROSQA-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1S,2R,4S,6S,7R)-4-((S)-Hydroxy-phenyl-methyl)-7,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decane-5-carboxylic acid tert-butyl ester 在 盐酸 、 sodium tetrahydroborate 、 水 作用下， 以 吡啶 为溶剂， 生成 (R)-2-hydroxy-1-phenylethyl benzoate
  参考文献：
  名称：

  乙二醛的新型手性合成等价物及其在O-保护的α-羟基醛的不对称合成中的应用

  摘要：

  对映异构纯2-甲酰基的N-Boc-1,3-恶唑烷7在83％的产率制备从stannyloxazolidine 4。在路易斯酸的存在下，将格利雅（Grignard）加成化合物7的甲酰基，得到非对映体纯的仲甲醇8。羟基的保护和恶唑烷环的未掩蔽得到O保护的α-羟基醛11，将其立即还原为相应的1,2-二醇12。

  DOI：

  10.1016/s0040-4039(99)00095-7

文献信息

• Recent Developments in the Area of Asymmetric Transfer Hydrogenation
  作者：Martin Wills、Matthew Palmer、Athene Smith、Jennifer Kenny、Tim Walsgrove

  DOI：10.3390/50100004

  日期：——

  The use of an enantiomerically pure amino alcohol, coupled to a transfer hydrogenation process, in the asymmetric catalysis of the reduction of ketones to alcohols, is described. The process works well for unfunctionalised ketones, affording e.e.s of up to 98%, and excellent conversions. We have recently extended, for the first time in this application, the scope of the methodology to the reductions of a-heteroatom substituted substrates, through the use of the appropriate protecting groups on each atom.

  描述了一种使用手性纯氨基醇与转移氢化过程结合的非对称催化方法，将酮还原为醇。该过程对未功能化的酮效果良好，提供高达98%的诠释率和优良的转化率。我们最近首次扩展了该方法在这一应用范围的适用性，通过在每个原子上使用适当的保护基团，对α-杂原子取代底物进行了还原。
• The Activation of Carboxylic Acids via Self-Assembly Asymmetric Organocatalysis: A Combined Experimental and Computational Investigation
  作者：Mattia Riccardo Monaco、Daniele Fazzi、Nobuya Tsuji、Markus Leutzsch、Saihu Liao、Walter Thiel、Benjamin List

  DOI：10.1021/jacs.6b09179

  日期：2016.11.9

  The heterodimerizing self-assembly between a phosphoric acid catalyst and a carboxylic acid has recently been established as a new activation mode in Brønsted acid catalysis. In this article, we present a comprehensive mechanistic investigation on this activation principle, which eventually led to its elucidation. Detailed studies are reported, including computational investigations on the supramolecular

  磷酸催化剂和羧酸之间的异二聚化自组装最近已被确立为布朗斯台德酸催化中的一种新活化模式。在本文中，我们对该激活原理进行了全面的机理研究，最终对其进行了阐明。报告了详细的研究，包括对超分子异二聚体的计算研究、催化循环的动力学研究，以及通过 DFT 计算对过渡态进行彻底分析，以合理化催化剂结构 - 选择性关系。在这些研究的基础上，我们开发了外消旋环氧化物的动力学拆分，其具有高选择性（高达 s = 93），以高对映纯度提供未反应的环氧化物和相应的受保护的 1,2-二醇。而且，
• Asymmetric Transfer Hydrogenation of α-Amino and α-Alkoxy Substituted Ketones
  作者：Jennifer A. Kenny、Matthew J. Palmer、Athene R. C. Smith、Tim Walsgrove、Martin Wills

  DOI：10.1055/s-1999-2906

  日期：——

  Through the use of appropriate protecting groups, the asymmetric transfer hydrogenation of ketones bearing heteroatoms at the α-position may be achieved in high yield and enantioselectivity.

  通过使用适当的保护基团，可以高产率和高对映选择性地实现δ位含有杂原子的酮的不对称转移氢化。
• Kinetic Resolution of 1,2-Diols Using Nitrogen-Tethered Bisimidazoline-Copper(I) Catalyzed Benzoylation
  作者：Takayoshi Arai、Tomoe Mizukami、Asami Mishiro、Akira Yanagisawa

  DOI：10.3987/com-08-s(n)59

  日期：——

  Nitrogen-tethered bisimidazoline (Nb-imidazoline) ligand was utilized in the Cu(I)-catalyzed benzoylation of 1,2-diols. With the assistance of i-Pr(2)NEt, the reaction of rac-1,2-diols with o-methylbenzoyl chloride was smoothly catalyzed by Nb-imidazoline-CuCl in CH(2)Cl(2) to give the corresponding o-methylbenzoylated secondary alcohols in tip to 79% ee.
• Kinetic Resolution of Diols and Pyridyl Alcohols by Cu(II)(borabox)-Catalyzed Acylation
  作者：Clément Mazet、Stephen Roseblade、Valentin Köhler、Andreas Pfaltz

  DOI：10.1021/ol060443t

  日期：2006.4.1

  Boron-bridged bisoxazoline (borabox) ligands have been used in the copper(II)-catalyzed benzoylation of pyridyl alcohols and 1,2-diols. Efficient kinetic resolution of 1,2-diols was achieved using both borabox and bisoxazoline (box) ligands. Borabox ligands induced high selectivities in the benzoylation of suitable pyridyl alcohols, where they outperformed bisoxazolines. In addition, highly enantioselective Cu(II)(borabox)catalyzed benzoylation has been used for the synthesis of both enantiomers of a pyridyl alcohol.