trans-(2S,3R)-2,3-epoxy-1-(4-methylphenyl)-3-(4-fluorophenyl)propan-1-one | 1181811-21-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-(2S,3R)-2,3-epoxy-1-(4-methylphenyl)-3-(4-fluorophenyl)propan-1-one
• 英文别名: [(2S,3R)-3-(4-fluorophenyl)oxiran-2-yl]-(4-methylphenyl)methanone
• CAS: 1181811-21-1
• 化学式: C₁₆H₁₃FO₂
• 分子量: 256.276
• InChiKey: FJVUDVTWTYCBOD-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-(2S,3R)-2,3-epoxy-1-(4-methylphenyl)-3-(4-fluorophenyl)propan-1-one 在 对甲苯磺酸 、 一水合肼 作用下， 以 xylene 为溶剂， 反应 3.0h， 生成 5-(4-fluorophenyl)-3-(4-methylphenyl)-1H-pyrazole
  参考文献：
  名称：

  Monoamine Oxidase Isoform-Dependent Tautomeric Influence in the Recognition of 3,5-Diaryl Pyrazole Inhibitors

  摘要：

  A series of 3,5-diaryl pyrazoles were prepared and assayed for their ability to inhibit reversibly monoamine oxidase-A (MAO-A) and monoamine oxidase B (MAO-B). Several compounds show inhibitory activity with concentration values in the nanomolar range. A computational work was carried out on the two most selective inhibitors that have tautomeric pyrazole forms. The binding free energies of these compounds for each MAO isoform were influenced by the tautomeric equilibria.

  DOI：

  10.1021/jm060868l
• 作为产物：
  描述：

  4-氟-4'-甲基查耳酮 在 双氧水 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 trans-(2S,3R)-2,3-epoxy-1-(4-methylphenyl)-3-(4-fluorophenyl)propan-1-one
  参考文献：
  名称：

  Monoamine Oxidase Isoform-Dependent Tautomeric Influence in the Recognition of 3,5-Diaryl Pyrazole Inhibitors

  摘要：

  A series of 3,5-diaryl pyrazoles were prepared and assayed for their ability to inhibit reversibly monoamine oxidase-A (MAO-A) and monoamine oxidase B (MAO-B). Several compounds show inhibitory activity with concentration values in the nanomolar range. A computational work was carried out on the two most selective inhibitors that have tautomeric pyrazole forms. The binding free energies of these compounds for each MAO isoform were influenced by the tautomeric equilibria.

  DOI：

  10.1021/jm060868l

文献信息

• One-pot synthesis of α,β-epoxy ketones through domino reaction between alkenes and aldehydes catalyzed by proline based chiral organocatalysts
  作者：Veeramanoharan Ashokkumar、Ayyanar Siva

  DOI：10.1039/c7ob00031f

  日期：——

  Proline based metal free organocatalysts were developed by using a new approach for the synthesis of epoxide derivatives through a domino reaction. This domino reaction (oxidative coupling) allows a direct access to epoxides from various alkenes and aldehydes through C–H functionalization and C–C/C–O bond formation. The catalytic efficiencies of the newly synthesized organocatalysts were also determined

  通过使用一种通过多米诺反应合成环氧化物衍生物的新方法，开发了基于脯氨酸的无金属有机催化剂。这种多米诺反应（氧化偶联）允许通过C–H功能化和C–C / C–O键形成直接从各种烯烃和醛中获得环氧化物。还通过多米诺反应在含有醛和烯烃衍生物的各种官能团的存在下通过多米诺反应测定了新合成的有机催化剂的催化效率，产率很高（高达95％），ee的产率高达99％。
• Crown-ether-modified cyclic dipeptides as supramolecular chiral catalysts
  作者：Christopher Bérubé、Normand Voyer

  DOI：10.1080/10610278.2017.1392521

  日期：2018.3.4

  the objective to develop supramolecular catalysts for useful chemical transformations, we report here a rapid and efficient solid-phase synthesis of novel cyclic dipeptides (crown-CDPs) with a diversity of L-DOPA derived crown ether substituents and stereochemistry. We prepared and characterized 14 crown-CDPs and evaluated their efficiency as supramolecular epoxidation catalysts in a water/hexanes biphasic

  摘要 为了开发用于有用化学转化的超分子催化剂，我们在此报告了一种快速有效的新型环二肽（冠 CDP）的固相合成，具有多种 L-DOPA 衍生的冠醚取代基和立体化学。我们制备并表征了 14 种冠 CDP，并评估了它们在水/己烷双相体系中作为超分子环氧化催化剂的效率。尽管对映选择性取决于取代基的性质，但在冠 CDP 存在下产率显着增加。报告的结果构成了感兴趣的手性环氧化物的有用方法，并进一步说明了环肽作为超分子催化剂的潜力。
• Asymmetric Epoxidation of Olefins with Chiral Bioinspired Manganese Complexes
  作者：Mei Wu、Bin Wang、Shoufeng Wang、Chungu Xia、Wei Sun

  DOI：10.1021/ol901400m

  日期：2009.8.20

  A novel series of chiral tetradentate N4 ligands together with their manganese complexes have been designed and synthesized. With 1 mol % manganese catalyst loading, the enantioselective epoxidation of olefins proceeds with nearly full conversion and enantiomeric excess values of up to 89 % for the first time.

  设计和合成了一系列新的手性四齿N 4配体及其锰配合物。在锰催化剂负载量为1 mol％的情况下，烯烃的对映选择性环氧化反应几乎以完全转化的方式进行，并且对映体过量值首次达到89％。
• Chiral Bioinspired Non-Heme Iron Complexes for Enantioselective Epoxidation of α,β-Unsaturated Ketones
  作者：Mei Wu、Cheng-Xia Miao、Shoufeng Wang、Xiaoxue Hu、Chungu Xia、Fritz E. Kühn、Wei Sun

  DOI：10.1002/adsc.201100267

  日期：2011.11

  Chiral bioinspired iron complexes of N4 ligands based on the ethylenediamine backbone display remarkable levels of enantioselectivity for the first time in the asymmetric epoxidation of α,β-unsaturated ketones using hydrogen peroxide (up to 87% ee) or peracetic acid as oxidant, respectively. Notablely, isotopic labeling with H218O strongly demonstrated that there is a reversible water binding step

  基于乙二胺骨架的N 4配体的手性生物启发铁络合物，在使用过氧化氢（最高87％ee）或过氧乙酸作为氧化剂分别对α，β-不饱和酮进行不对称环氧化时，首次显示出显着的对映选择性。。值得注意的是，用H 2 18 O进行同位素标记强烈表明，在生成重要中间体之前，存在可逆的水结合步骤。此外，复杂的[L 2的Fe（III）2（μ-O）（μ-CH 3 CO 2）] 3+HR-MS鉴定出通常源自LFe（IV）O物种的衰变或许多铁配合物的热力学阱。此外，提出了可能的机理，LFe（V）O可能是催化体系中的主要活性中间体。
• Biomimetic epoxidation in aqueous media catalyzed by cyclic dipeptides
  作者：Christopher Bérubé、Normand Voyer

  DOI：10.1080/00397911.2016.1141428

  日期：2016.3.3

  We have developed a practical epoxidation of electron-deficient enones in aqueous media using cyclic dipeptides as bioinspired green catalyst. Optimizing the reaction conditions in a triphasic system led to efficient conditions providing epoxides with good enantioselectivities. Depending on the catalyst substituent chirality, both enantiomers are obtained. The cyclic rigidity impacts significantly the enantioselectivity.