methyl 2-benzyl-3-hydroxy-3-phenylpropanoate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: methyl 2-benzyl-3-hydroxy-3-phenylpropanoate
• 英文别名: Methyl 2-benzyl-3-hydroxy-3-phenylpropanoate
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: UJYGQDSAQXINNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  苯甲醛 在 四(三苯基膦)钯 、 CuF(PPh₃)₃*2MeOH 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 cesium fluoride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 methyl 2-benzyl-3-hydroxy-3-phenylpropanoate
  参考文献：
  名称：

  Copper catalyzed tandem conjugated borylation–aldol reaction

  摘要：

  We investigated the tandem conjugated borylation-aldol reaction catalyzed by copper complexes. After identification and optimisation of the catalytic system, the scope of the reaction was evaluated and the diastereoselectivity was studied on both linear and cyclic activated alkenes. Finally, the use of some selected borylated aldol adducts in two classical transformations was investigated. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.062

文献信息

• Cobalt-Catalyzed Reductive Multicomponent Synthesis of β-Hydroxy- and β-Aminocarbonyl Compounds under Mild Conditions
  作者：Jérôme Paul、Marc Presset、Frédéric Cantagrel、Erwan Le Gall、Eric Léonel

  DOI：10.1002/chem.201604251

  日期：2017.1.5

  The cobalt‐catalyzed multicomponent reaction between sp2‐hybridized organic halides, Michael acceptors, and unsaturated electrophiles has been developed. The reaction proceeds through a formal conjugate addition/aldol or aza‐aldol (Mannich) tandem reaction initiated by the in situ metalation of the organic halide by cobalt catalysis. The essentially new reaction conditions that have been developed

  已经开发了sp 2杂交的有机卤化物，Michael受体和不饱和亲电试剂之间钴催化的多组分反应。该反应通过正式的共轭加成/醛醇或氮杂-醛醇（曼尼希）串联反应进行，该反应由钴催化有机卤化物的原位金属化引发。已经开发出的本质上是新的反应条件是非常温和且经济的。在这些条件下，可以以高到高收率获得各种各样的β-羟基和β-氨基羰基化合物。
• An Essentially Mild and Efficient Catalyst System for the Activation of Carbonyl Compounds and Their Derivatives. The Combined Use of Trimethylsilyl Chloride and Tin(II) Chloride
  作者：Nobuharu Iwasawa、Teruaki Mukaiyama

  DOI：10.1246/cl.1987.463

  日期：1987.3.5

  An essentially mild and efficient catalyst system, the combined use of trimethylsilyl chloride and tin(II) chloride, is effectively employed for the activation of acetals, aldehydes, orthoesters, and α,β-unsaturated ketones to accomplish the reaction with silyl enol ethers to give the corresponding addition products in good yields.

  一种本质上温和且高效的催化剂体系，三甲基氯化硅烷和氯化锡（II）的组合使用，有效地用于缩醛、醛、原酸酯和 α,β-不饱和酮的活化，以完成与甲硅烷基烯醇醚的反应，以良好的收率给出相应的加成产物。
• Enantioselective and Diastereoselective Ir-Catalyzed Hydrogenation of α-Substituted β-Ketoesters via Dynamic Kinetic Resolution
  作者：Guoxian Gu、Jiaxiang Lu、Ouran Yu、Jialin Wen、Qin Yin、Xumu Zhang

  DOI：10.1021/acs.orglett.8b00433

  日期：2018.4.6

  An iridium/f-amphol catalytic system for the enantioselective hydrogenation of α-substituted β-ketoesters via dynamic kinetic resolution is reported. The desired anti products were obtained in high yields (up to 98%) with good diastereoselectivity (up to 96:4 diastereometic ratio (dr)) and excellent enantioselectivity (up to >99% enantiomeric excess (ee)). A catalytic model is proposed to explain the

  报道了用于通过动态动力学拆分对α-取代的β-酮酸酯进行对映选择性氢化的铱/ f-amphol催化体系。以高收率（高达98％），良好的非对映选择性（高达96：4的非对映比率（dr））和优异的对映选择性（高达> 99％的对映体过量（ee））获得所需的抗产物。提出了催化模型来解释立体选择性。
• Sterically Hindered Chiral Ferrocenyl P,N,N-Ligands for Highly Diastereo-/Enantioselective Ir-Catalyzed Hydrogenation of α-Alkyl-β-ketoesters via Dynamic Kinetic Resolution
  作者：Chuan-Jin Hou、Xiang-Ping Hu

  DOI：10.1021/acs.orglett.6b02828

  日期：2016.11.4

  A new class of sterically hindered chiral ferrocenyl P,N,N-ligands have been prepared through a two-step transformation from (Sc,Rp)-PPFNH2, in which a new (R)-stereogenic center at the pyridinylmethyl position was generated in high diastereoselectivity. With these newly developed P,N,N-ligands, Ir-catalyzed asymmetric hydrogenation of various α-alkyl-substituted β-aryl-β-ketoesters via dynamic kinetic

  通过从（S c，R p）-PPFNH 2的两步转化制备了新型的空间位阻性手性二茂铁基二茂铁基P，N，N-配体，其中在吡啶基甲基位置上有一个新的（R）-立体异构中心产生的非对映异构体选择性高。借助这些新开发的P，N，N配体，首次在高非对映体和对映体选择性下，通过动态动力学拆分实现了Ir催化的各种α-烷基取代的β-芳基-β-酮酸酯的不对称氢化，导致了多种光学活性的反-β-羟基酯含量高达99％ee。研究表明，这些配体的吡啶基甲基位置上的额外立体中心对于实现这种氢化作用至关重要。
• A NEW METHOD FOR THE PREPARATION OF β-HYDROXYESTERS. THE TITANIUM TETRACHLORIDE-PROMOTED REACTION OF KETENE ALKYL TRIALKYLSILYL ACETALS WITH CARBONYL COMPOUNDS
  作者：Kazuhiko Saigo、Masaaki Osaki、Teruaki Mukaiyama

  DOI：10.1246/cl.1975.989

  日期：1975.9.5

  In the presence of TiCl4, ketene alkyl trialkylsilyl acetals, prepared from α-lithio esters and a trialkylsilyl halide, react with aldehydes and ketones at −78°C to afford the corresponding β-hydroxyesters and β-trialkylsiloxyesters in good yields.

  在 TiCl4 存在下，由 α-锂硫酯和三烷基甲硅烷基卤化物制备的乙烯酮烷基三烷基甲硅烷基缩醛在 -78°C 下与醛和酮反应，以良好的收率得到相应的 β-羟基酯和 β-三烷基甲硅烷氧基酯。