1-phenyl-3-(o-bromophenyl)-2,3-epoxy-1-propanone | 1431527-08-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-phenyl-3-(o-bromophenyl)-2,3-epoxy-1-propanone
• 英文别名: (3-(2-bromophenyl)oxiran-2-yl)(phenyl)methanone；[3-(2-Bromophenyl)oxiran-2-yl]-phenylmethanone
• CAS: 1431527-08-0
• 化学式: C₁₅H₁₁BrO₂
• 分子量: 303.155
• InChiKey: LBQHGGUBHGQVQN-UHFFFAOYSA-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：

  1-phenyl-3-(o-bromophenyl)-2,3-epoxy-1-propanone 在 sodium dithionite 、 sodium carbonate 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 12.0h， 以95%的产率得到3-(2-bromophenyl)-3-hydroxy-1-phenylpropan-1-one
  参考文献：
  名称：

  PAA-supported Hantzsch 1,4-dihydropyridine ester: an efficient catalyst for the hydrogenation of α,β-epoxy ketones

  摘要：

  A new type of water-soluble polymer-supported NADH co-enzyme model-FAA (polyacrylic acid)-supported Hantzsch 1,4-dihydropyridine ester (PM-HEH) was designed and synthesized. Catalytic amount of the supported reagent was used in the hydrogenation of alpha,beta-epoxy ketones to the corresponding beta-hydroxy ketones and showed great catalytic efficiency in the reduction reaction. This PAA-HEH was an optimal potential for recycling use. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.112
• 作为产物：
  描述：

  苯乙酮 在 双氧水 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 6.0h， 生成 1-phenyl-3-(o-bromophenyl)-2,3-epoxy-1-propanone
  参考文献：
  名称：

  Biomimetic hydrogenation: a reusable NADH co-enzyme model for hydrogenation of α,β-epoxy ketones and 1,2-diketones

  摘要：

  A biomimetic method has been developed to transform alpha,beta-epoxy ketones or 1,2-diketones into corresponding beta-hydroxy ketones or alpha-hydroxy ketones using a catalytic amount of BNAH or BNA(+)Br(-). The regeneration of BNAH or BNA(+)Br(-) is achieved by a mixture of HCOOH/Et3N. A radical mechanism is proposed to explain these observations. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.047

文献信息

• Selectfluor-Mediated Simultaneous Cleavage of C–O and C–C Bonds in α,β-Epoxy Ketones Under Transition-Metal-Free Conditions: A Route to 1,2-Diketones
  作者：Heng Wang、Shaobo Ren、Jian Zhang、Wei Zhang、Yunkui Liu

  DOI：10.1021/acs.joc.5b00857

  日期：2015.7.2

  Selectfluor-mediated simultaneous cleavage of C–O and C–C bonds in α,β-epoxy ketones has been successfully achieved under transition-metal-free conditions. The reaction gives 1,2-diketone compounds in moderate to good yields involving a ring-opening/benzoyl rearrangement/C–C bond cleavage sequence under oxidative conditions.

  在无过渡金属条件下，Selectfluor介导的α，β-环氧酮中C-O和C-C键的同时裂解已成功实现。该反应以中等至良好的收率得到1,2-二酮化合物，包括在氧化条件下的开环/苯甲酰基重排/ CC键断裂序列。
• [4 + 2] Heterocyclization for Efficient Formation of Substituted Quinoxalines through Carbon-Oxygen Bonds Cleavage
  作者：Man-Su Tu、Hai-Wei Xu、Wei Fan、Bo Jiang、Shu-Jiang Tu

  DOI：10.1002/jhet.2128

  日期：2015.5

  A new domino strategy for efficient synthesis of highly functionalized quinoxaline derivatives via [4 + 2] heterocyclization involving ring‐opening of oxirane process has been developed. The reaction promoted by Cs2CO3 was easy to perform in a simple operation from common and inexpensive starting materials. The bisfunctionalization of quinoxaline framework including C2 benzylation and C3 arylation

  已开发出一种新的多米诺骨牌策略，可通过[4 + 2]杂环化（包括环氧乙烷工艺的开环）有效合成高度官能化的喹喔啉衍生物。由Cs 2 CO 3促进的反应易于由普通且廉价的起始原料以简单的操作进行。喹喔啉骨架的双功能化（包括C2苄基化和C3芳基化）很容易以多米诺骨牌的方式实现，涉及裂解1,3-二芳基-2,3-环氧丙烷-1-酮的三个C-O键。
• Preparation of Mesoporous Zeolite ETS-10 Catalysts for High-Yield Synthesis of α,β-Epoxy Ketones
  作者：Mei Xiang、Xiaojun Ni、Xianfeng Yi、Anmin Zheng、Wenchang Wang、Mingyang He、Jing Xiong、Taotao Liu、Yuli Ma、Pengyuan Zhu、Xiang Zheng、Tiandi Tang

  DOI：10.1002/cctc.201402839

  日期：2015.2

  importance to synthetic chemistry. For this purpose, a mesoporous zeolite ETS‐10 (METS‐10) is synthesized by using a mesoscale silane surfactant as a template and applied to achieve highly efficient syntheses of α,β‐epoxy ketones by employing simple alkenes and aldehydes as starting materials. The high activity of the METS‐10 catalyst is attributed to its unique porous structure and basicity. Electron

  开发高活性的非均相催化剂以有效构建有价值的结构单元对于合成化学非常重要。为此，以中尺度硅烷表面活性剂为模板合成了介孔沸石ETS-10（METS-10），并以简单的烯烃和醛为原料将其应用于高效合成α，β-环氧酮。METS-10催化剂的高活性归因于其独特的多孔结构和碱度。电子顺磁共振表征结果和理论计算实验数据表明，METS-10催化剂上的强碱性位点可以活化反应底物和中间体。此外，METS-10催化剂中的中孔有利于传质并进一步提高了催化活性。
• Highly Diastereo- and Enantioselective Organocatalytic Domino Michael/Aldol Reaction of Acyclic 3-Halogeno-1,2-Diones to α,β-Unsaturated Aldehydes
  作者：Alice Lefranc、Laure Guénée、Alexandre Alexakis

  DOI：10.1021/ol400697n

  日期：2013.5.3

  The first organocatalytic diastereo- and enantioselective domino Michael/aldol reaction of 3-halogeno-1,2-diones to α,β-unsaturated aldehydes has been achieved. This transformation tolerates a large variety of electronically different substituents on both reactive partners and allows the synthesis of challenging cyclopentanone derivatives with four contiguous stereogenic centers in excellent diastereoselectivities

  已经实现了3-卤代1,2-二酮与α，β-不饱和醛的第一有机催化非对映和对映选择性多米诺迈克尔/醛醇缩合反应。这种转化在两个反应伙伴上都可以耐受多种电子上不同的取代基，并可以合成具有四个非连续立体异构中心（> 20：1 dr）且产率高（69-97％）的具有挑战性的具有四个连续立体中心的环戊酮衍生物。对映选择性（高达94％ee）。
• Design and synthesis of bi-functional Co-containing zeolite ETS-10 catalyst with high activity in the oxidative coupling of alkenes with aldehydes for preparing α,β-epoxy ketones
  作者：Jun Hu、Feifei Xia、Fengli Yang、Jushi Weng、Pengfei Yao、Chunzhi Zheng、Chaojie Zhu、Tiandi Tang、Wenqian Fu

  DOI：10.1039/c7ra06828j

  日期：——

  work, Co (or Ni)-containing mesoporous zeolite ETS-10 (Co-METS-10 and Ni-METS-10) with both metal and strong basic sites were synthesized and applied for the direct oxidative coupling of alkenes with benzaldehydes to synthesize α,β-epoxy ketones. Co (or Ni)-METS-10 catalysts show high activity and product selectivity, as compared to metal-free mesoporous zeolite ETS-10 (METS-10). This feature is attributed

  开发用于有机合成的高效多相催化剂在现代合成化学中非常重要。在这项工作中，合成了同时具有金属和强碱性位点的含Co（或Ni）的介孔沸石ETS-10（Co-METS-10和Ni-METS-10），并将其用于烯烃与苯甲醛的直接氧化偶合。合成α，β-环氧酮。与无金属的介孔沸石ETS-10（METS-10）相比，Co（或Ni）-METS-10催化剂显示出高活性和产物选择性。此特征归因于以下事实：高度分散的Co（或Ni）物种可以促进叔叔-丁基氢过氧化物转化为更多的烷氧基和烷基过氧自由基，这会触发烯烃与醛和烷基过氧自由基加成反应以形成β-过氧酮。同时，Co（或Ni）-METS-10催化剂上的碱性位有利于由β-过氧酮形成α，β-环氧酮。