(2S,3R)-[1,1'-biphenyl]-4-yl(3-phenyloxiran-2-yl)methanone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (2S,3R)-[1,1'-biphenyl]-4-yl(3-phenyloxiran-2-yl)methanone
• 英文别名: trans‐(+)‐2,3‐epoxy‐1‐(biphen‐4‐yl)‐3‐phenylpropan‐1‐one；[(2S,3R)-3-phenyloxiran-2-yl]-(4-phenylphenyl)methanone
• 化学式: C₂₁H₁₆O₂
• 分子量: 300.357
• InChiKey: YCFFVRPHPWIPTD-NHCUHLMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-biphenyl-4'-yl-3-phenylprop-2-enone 在 叔丁基过氧化氢 、 4 A molecular sieve 、 chiral pyrrolidinylmethanol-based dendritic reagent 作用下， 以 四氯化碳 为溶剂， 反应 144.0h， 生成 (2S,3R)-[1,1'-biphenyl]-4-yl(3-phenyloxiran-2-yl)methanone 、 (2R,3S)-[1,1'-biphenyl]-4-yl(3-phenyloxiran-2-yl)methanone
  参考文献：
  名称：

  Effective and recyclable dendritic ligands for the enantioselective epoxidation of enones

  摘要：

  An operationally simple and mild protocol for the catalytic enantioselective epoxidation of enones has been established using a series of chiral pyrrolidinylmethanol-based dendritic catalysts and tert-butyl hydroperoxide (TBHP) as an oxidant. The epoxides have been obtained in good yields and ee up to 78%. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2006.02.019

文献信息

• Synthesis of xylal‐ and arabinal‐based crown ethers and their application as asymmetric phase transfer catalysts
  作者：Tamás Nemcsok、Zsolt Rapi、Péter Bagi、György Keglevich、Péter Bakó

  DOI：10.1002/chir.23149

  日期：2020.1

  from l‐ and d‐xylose, and l‐ and d‐arabinose, respectively. These monosaccharide‐based chiral macrocycles were tested as phase transfer catalysts in a few asymmetric reactions. The xylal‐based crown compounds proved to be efficient catalysts in a few liquid‐liquid phase reactions. The epoxidation of trans‐chalcone and the Darzens condensation of α‐chloroacetophenone with benzaldehyde took place with

  基于arabinal新xylal-和单氮杂-15-冠醚5合成从开始升-和ð木糖，和升和- d分别-arabinose。这些基于单糖的手性大环化合物在一些不对称反应中作为相转移催化剂进行了测试。在一些液相-液相反应中，基于木糖的冠状化合物被证明是有效的催化剂。反式的环氧化α-氯苯乙酮与苯甲醛的查尔酮和达岑（Darzens）缩合反应具有完全非对映选择性，分别高达ee的77％和ee的58％。发现查尔酮和α-氯乙酰苯的芳香环中的取代基对对映选择性有影响。最高的ee值来自4-氯查尔酮的环氧化（81％ee）和2-萘基类似物的反应（96％ee），而4-苯基-α-氯乙酰苯与苯甲醛的Darzens缩合反应，检测到的最大ee为91％。冠环中单糖单元的构型影响合成的环氧酮的绝对构型。
• Kinetic resolution of 2,3-epoxy 3-aryl ketones via catalytic asymmetric ring-opening with pyrazole derivatives
  作者：Tianyu Huang、Lili Lin、Xiaolei Hu、Jianfeng Zheng、Xiaohua Liu、Xiaoming Feng

  DOI：10.1039/c5cc02179k

  日期：——

  A highly efficient catalytic kinetic resolution of 2,3-epoxy 3-aryl ketones via asymmetric ring-opening with pyrazole derivatives has been achieved by using a chiral N,N′-dioxide–Sc(iii) complex as the catalyst.

  一种高效的催化动力学拆分2,3-环氧基3-芳基酮，通过使用手性N,N′-二氧化物-Sc(iii)复合物作为催化剂，通过与吡唑衍生物的不对称环开启实现。
• Asymmetric C–C bond formation via Darzens condensation and Michael addition using monosaccharide-based chiral crown ethers
  作者：Péter Bakó、Zsolt Rapi、György Keglevich、Tamás Szabó、Péter L. Sóti、Tamás Vígh、Alajos Grűn、Tamás Holczbauer

  DOI：10.1016/j.tetlet.2011.01.094

  日期：2011.3

  phase asymmetric Darzens condensations were promoted by d-glucose- and d-mannose-based crown ethers. The corresponding aromatic and heteroaromatic α,β-epoxyketones were obtained with moderate to high enantioselectivities (up to 96%) as well as diastereoselectivities (up to 98:2) under mild reaction conditions. The absolute configurations of several of the epoxyketones were determined by single crystal

  d-葡萄糖和d-甘露糖基冠醚促进了液相-液相不对称Darzens缩合反应。在温和的反应条件下，获得了具有中等至高对映选择性（最高96％）以及非对映选择性（最高98：2）的相应芳族和杂芳族α，β-环氧酮。通过单晶X射线分析确定几种环氧酮的绝对构型。乙酰氨基丙二酸二乙酯在反式-β-硝基烯烃中的迈克尔加成反应是在固-液两相系统中，在以d-葡萄糖为基础的冠状催化剂存在下，ee高达99％。
• Asymmetric phase transfer Darzens reactions catalyzed by d-glucose- and d-mannose-based chiral crown ethers
  作者：Zsolt Rapi、Péter Bakó、György Keglevich、Áron Szöllősy、László Drahos、Adrienn Botyánszki、Tamás Holczbauer

  DOI：10.1016/j.tetasy.2012.04.006

  日期：2012.4

  and d-mannose-based crown ethers 1 and 2 as the catalyst. The use of d-glucose-based lariat ether 1 as the catalyst gave the best results. The reaction of 4-phenyl-α-chloroacetophenone, 2-chloro-1-tetralone, and 2-chloro-1-indanone with various aromatic aldehydes afforded the corresponding aromatic α,β-epoxyketones in moderate to high enantiomeric excess (ee up to 96%) under mild reaction conditions

  液相-液相不对称Darzens缩合反应是在基于d-葡萄糖和d-甘露糖的冠醚1和2的存在下进行的。使用基于d-葡萄糖的套​​索状醚1作为催化剂可获得最佳结果。4-苯基-α-氯乙酰苯酮，2-氯-1-四氢萘酮和2-氯-1-茚满酮与各种芳族醛的反应可得到相应的芳族α，β-环氧酮，其对映体过量至中度对映体过量（ee最高可达96％）在温和的反应条件下。用作反应物的苯甲醛的取代基对化学收率和对映体过量有重大影响。一些环氧酮产品的绝对构型是通过单晶X射线分析确定的。
• Effective and recyclable dendritic ligands for the enantioselective epoxidation of enones
  作者：Xinyuan Liu、Yawen Li、Guangyin Wang、Zhuo Chai、Yongyong Wu、Gang Zhao

  DOI：10.1016/j.tetasy.2006.02.019

  日期：2006.3

  An operationally simple and mild protocol for the catalytic enantioselective epoxidation of enones has been established using a series of chiral pyrrolidinylmethanol-based dendritic catalysts and tert-butyl hydroperoxide (TBHP) as an oxidant. The epoxides have been obtained in good yields and ee up to 78%. (c) 2006 Published by Elsevier Ltd.