(2S,3R)-epoxy-3-phenyl-1-(4-bromophenyl)-propan-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R)-epoxy-3-phenyl-1-(4-bromophenyl)-propan-1-one
• 英文别名: (4-bromophenyl)(3-phenyloxiran-2-yl)methanone；(4-bromophenyl)((2S,3R)-3-phenyloxiran-2-yl) methanone；(4-bromophenyl)-[(2S,3R)-3-phenyloxiran-2-yl]methanone
• 化学式: C₁₅H₁₁BrO₂
• 分子量: 303.155
• InChiKey: JNLVEYCRYFQKCW-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3R)-epoxy-3-phenyl-1-(4-bromophenyl)-propan-1-one 在 溴化锡 作用下， 以 苯 为溶剂， 反应 0.25h， 以86.1%的产率得到3-bromo-1-(4-bromophenyl)-2-hydroxy-3-phenylpropan-1-one
  参考文献：
  名称：

  Substituenteneffekte in den13C-NMR-Spektren von diastereomeren Chalkondihalogeniden, 10. Mitt.: Erste Synthese und Konfigurationsbestimmung vonthreo-Chalkonbromhydrinen

  摘要：

  The first synthesis of threo chalcone bromohydrins was realized by reaction of trans chalcone epoxides with SnBr4 in molar ratios from 1:1 to 2:1. The compounds were obtained in high yields and isomeric purity. Their configuration was determined as threo by different methods based on C-13-NMR shifts of C-alpha and C-beta atoms.

  DOI：

  10.1007/bf01045300
• 作为产物：
  描述：

  1-(4-bromophenyl)-3-phenyl-2-propen-1-one 在 双氧水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 (2S,3R)-epoxy-3-phenyl-1-(4-bromophenyl)-propan-1-one
  参考文献：
  名称：

  Ring opening of α,β-epoxy phenyl ketones with ceric ammonium nitrate (CAN) and potassium bromide

  摘要：

  利用硝酸铵铈（CAN）和溴化钾协同实现了 α、β-环氧苯基酮的开环反应。该反应在 β-C 处发生区域选择性反应，主要生成合成-β-溴-α-羟基酮。

  DOI：

  10.1139/v07-148

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％。
• Diaryl-2-pyrrolidinemethanols catalyzed enantioselective epoxidation of α,β-enones: new insight into the effect of structural modification of the catalyst on reaction efficiency
  作者：Alessandra Lattanzi、Alessio Russo

  DOI：10.1016/j.tet.2006.10.005

  日期：2006.12

  Catalytic enantioselective epoxidation of α,β-unsaturated ketones promoted by diaryl-2-pyrrolidinemethanols and tert-butyl hydroperoxide (TBHP) is described. Investigation on structural modifications of the diaryl-2-pyrrolidinemethanols showed that fine tuning of the stereoelectronics of the substituents on the aryl moiety is important to achieve high efficiency. By employing a structurally optimized

  描述了由二芳基-2-吡咯烷甲醇和叔丁基氢过氧化物（TBHP）促进的α，β-不饱和酮的催化对映选择性环氧化。对二芳基-2-吡咯烷甲醇的结构修饰的研究表明，对芳基部分上的取代基的立体电子进行精细调节对于实现高效率很重要。通过使用结构优化的有机催化剂，可以使用显着降低的负载量（10 mol％）在室温下以高收率和高达90％ee的产率生产环氧化物。
• Asymmetric synthesis of new γ-butenolides via organocatalyzed epoxidation of chalcones
  作者：Lucas C. C. Vieira、Bianca T. Matsuo、Lorena S. R. Martelli、Mayara Gall、Marcio W. Paixão、Arlene G. Corrêa

  DOI：10.1039/c7ob00165g

  日期：——

  medicinally important agents. In this work we describe a new metal-free sequential strategy for the asymmetric synthesis of substituted γ-butenolides having epoxychalcones as the advanced intermediate. Using the optimized reaction conditions, we were able to carry out the three-step sequence, epoxidation, olefination and hydrolysis, with only one single chromatographic purification of the final product

  γ-丁烯内酯已被公认为许多天然产物和医学上重要的药物的重要结构框架。在这项工作中，我们描述了一种新的无金属顺序策略，用于不对称合成以环氧查耳酮为高级中间体的取代γ-丁烯内酯。使用优化的反应条件，我们能够进行三步操作，环氧化，烯化和水解，仅需对最终产物进行一次色谱纯化，即可以中等的总收率和良好的对映体过量提供新的对映异构体富集的γ-丁烯内酯。 。
• Enantioselective catalytic epoxidation of α,β-enones promoted by fluorous α,α-diaryl-l-prolinols
  作者：Haifeng Cui、Yawen Li、Changwu Zheng、Gang Zhao、Shizheng Zhu

  DOI：10.1016/j.jfluchem.2007.08.012

  日期：2008.1

  Enantioselective (up to 87% ee) epoxidation of a variety of α,β-enones to form α,β-epoxy ketones is described using a series of fluorous α,α-diaryl-l-prolinols as bifuncational organocatalysts and tert-butyl hydrogenperoxide (TBHP) as an oxidant.

  描述了使用一系列含氟的α，α-二芳基-1-脯氨醇作为双官能有机催化剂和叔丁基过氧化氢，对多种α，β-烯酮进行对映选择性（高达ee的87％）环氧化以形成α，β-环氧酮（TBHP）作为氧化剂。
• Asymmetric Epoxidation oftrans-Chalcones Organocatalyzed by β-Amino Alcohols
  作者：Alessio Russo、Alessandra Lattanzi

  DOI：10.1002/ejoc.200800140

  日期：2008.6

  examined as organocatalysts in the epoxidation of trans-chalcones with tert-butyl hydroperoxide as the oxidant. Primary, secondary, and tertiary β-amino alcohols are able to promote the reaction with variable activity and level of asymmetric induction. Subtle modifications to the structures of simple primary β-amino alcohol strongly influenced their efficiency in the epoxidation. They are promising catalysts

  在以叔丁基氢过氧化物作为氧化剂的反式查耳酮环氧化反应中，环状和非环状 β-氨基醇被用作有机催化剂。伯、仲和叔 β-氨基醇能够以可变的活性和不对称诱导水平促进反应。对简单伯 β-氨基醇结构的细微修改强烈影响了它们在环氧化中的效率。它们是很有前途的催化剂，可在室温下提供高达 52 % ee 的反式查耳酮环氧化物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)