benzoic acid (S,S)-2-hydroxy-1,2-diphenylethyl ester | 163438-23-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: benzoic acid (S,S)-2-hydroxy-1,2-diphenylethyl ester
• 英文别名: (1S,2S)-2-hydroxy-1,2-diphenylethyl benzoate；[(1S,2S)-2-hydroxy-1,2-diphenylethyl] benzoate
• CAS: 163438-23-1
• 化学式: C₂₁H₁₈O₃
• 分子量: 318.372
• InChiKey: PEUPYKYBVPJDCE-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  (-)-(4S,5S)-4,5-diphenyl-1,3-dioxolan-2-one 、 苯基锂 以 四氢呋喃 为溶剂， 生成 benzoic acid (S,S)-2-hydroxy-1,2-diphenylethyl ester
  参考文献：
  名称：

  Chemical Synthesis and Biological Evaluation of C-2 Taxoids

  摘要：

  An efficient, general method for the synthesis of 1,2-hydroxy esters by regioselective nucleophilic opening of 1,2-cyclic carbonate systems has been developed. A reliable and practical route giving access to the taxoid carbonate 2 from the readily available 10-deacetylbaccatin III (13) has been established. Nucleophilic opening of the carbonate 2 with a variety of nucleophiles provided a number of novel C-2 Taxols. Water-soluble taxoid onium salts (e.g., 31e, 31n, 32, and 34b) were also synthesized and studied. A selected number of taxoids were subjected to cytotoxicity and tubulin polymerization assays as well as in vivo studies. The results of these studies are reported herein.

  DOI：

  10.1021/ja00114a005

文献信息

• Organocatalytic Asymmetric Hydrolysis of Epoxides
  作者：Mattia Riccardo Monaco、Sébastien Prévost、Benjamin List

  DOI：10.1002/anie.201400170

  日期：2014.7.28

  The hydrolytic ring opening of epoxides is an important biosynthetic transformation and is also applied industrially. We report the first organocatalytic variant of this reaction, exploiting our recently discovered activation of carboxylic acids with chiral phosphoric acids via heterodimerization. The methodology mimics the enzymatic mechanism, which involves an enzyme‐bound carboxylate nucleophile

  环氧化合物的水解开环是重要的生物合成转化，也已在工业上应用。我们报道了该反应的第一个有机催化变体，它利用了我们最近发现的通过异二聚作用与手性磷酸对羧酸的活化作用。该方法学模拟了酶促机制，其中涉及酶结合的羧酸盐亲核试剂。新设计的磷酸催化剂显示高立体控制中的desymmetrization内消旋环氧化物。该方法在环状，酰基，芳族和脂族底物上显示出广泛的通用性。我们还将我们的方法应用于简单烯烃的第一个高度对映选择性的抗二羟基化反应中。
• Asymmetric benzoylation of hydrobenzoin by copper(ii) bis(oxazoline) anchored onto ordered mesoporous silicas and their carbon replicas
  作者：Ana Rosa Silva、Liliana Carneiro、Ana P. Carvalho、João Pires

  DOI：10.1039/c3cy00232b

  日期：——

  transformation. Using the two ordered mesoporous silicas as supports good selectivities, with comparable yields and TONs to the homogeneous phase reaction, were obtained. Furthermore these two heterogeneous catalysts are more stable upon reuse than the corresponding ordered carbon replica materials. One of the former heterogeneous catalysts, with mesoporous silica as a support, could be further reused for 4

  将具有商业手性双（恶唑啉）的铜（II）配合物锚定到有序介孔上硅石材料及其各自的碳复制品。用ICP-AES测定过渡金属络合物负载在介孔结构固体上的量，并通过元素分析，FTIR，TG / DSC和N 2等温线对材料进行表征吸附温度为-196°C。首次使用锚定的商业双（恶唑啉）配体在异相中进行1,2-二醇的不对称苯甲酰化。检查了介孔材料类型对催化参数的影响，以及在几个催化循环中对催化剂的再利用。在这种不对称有机转化中，所有制备的复合材料均具有活性，选择性和对映选择性。使用两种有序的介孔二氧化硅作为载体，具有良好的选择性，并具有与均相反应相当的产率和TON。此外，这两种非均相催化剂在再利用时比相应的有序碳复制材料更稳定。一种以前的非均相催化剂，具有介孔硅石 作为支持，可以在连续4个循环中进一步重复使用，而不会显着降低选择性，TON或对映选择性。
• Reaction Optimization Using Solid-Phase Catalysis-CD HTS:  <i>N</i>b-Imidazoline−Cu(I)-Catalyzed Asymmetric Benzoylation of 1,2-Diols
  作者：Takayoshi Arai、Tomoe Mizukami、Akira Yanagisawa

  DOI：10.1021/ol0702122

  日期：2007.3.1

  Catalytic asymmetric benzoylation of 1,2-diols has been developed using a solid-phase asymmetric catalyst. The reaction conditions were optimized by the screening of different metal salts, solvents, bases, and temperatures. High-throughput screening was performed using circular dichroism detection, and the results revealed that Nb-imidazoline-copper(I) in combination with diisopropylethylamine was

  已经使用固相不对称催化剂开发了1，2-二醇的催化不对称苯甲酰基化。通过筛选不同的金属盐，溶剂，碱和温度来优化反应条件。使用圆二色性检测进行了高通量筛选，结果表明Nb-咪唑啉-铜（I）与二异丙基乙胺结合可以催化高对映体选择性，单苯甲酰化产物的收率高，对映体过量高达95％ee。[反应：看文字]
• SupraBox: Chiral Supramolecular Oxazoline Ligands
  作者：Marco Durini、Eleonora Russotto、Luca Pignataro、Oliver Reiser、Umberto Piarulli

  DOI：10.1002/ejoc.201200516

  日期：2012.10

  second one. A library of 16 SupraBox ligands was prepared using 5 differently substituted oxazoline nuclei, 4 linkers and 3 different urea substituents. The formation of copper(II) and palladium(II) complexes was investigated by MS, UV/Vis and 1H-NMR spectroscopy. The SupraBox library was screened in the copper-catalyzed asymmetric benzoylation of vic-diols. Good selectivities were obtained in the kinetic

  研究了一类新的恶唑啉配体，名为 SupraBox。这些配体具有额外的尿素官能度，通过在一个配体的尿素 N-氢和第二个配体的羰基氧之间建立氢键，在过渡金属配合物中生成超分子双齿配体。使用 5 个不同取代的恶唑啉核、4 个接头和 3 个不同的尿素取代基制备了 16 个 SupraBox 配体库。通过 MS、UV/Vis 和 1H-NMR 光谱研究了铜 (II) 和钯 (II) 配合物的形成。SupraBox 文库在铜催化的vic-二醇的不对称苯甲酰化中进行筛选。在外消旋氢安息香的动力学拆分 [高达 86 % ee 和选择性 (s) = 28] 和内消旋对苯二酚的去对称化（高达 88 % ee）中获得了良好的选择性。
• Chiral lactones
  申请人：Onishi Tomoyuki

  公开号：US20060205816A1

  公开（公告）日：2006-09-14

  Lactones represented by the formula 2 a or 2 b: are provided, where each Ph is, independently, an unsubstituted or substituted phenyl group. These lactones are suitable for the synthesis of various α-hydroxy acids and 1,2-diols.

  提供了由公式2a或2b代表的内酯，其中每个Ph分别是未取代或取代的苯基团。这些内酯适用于合成各种α-羟基酸和1,2-二醇。