(E)-3-mesityl-1-(4-methoxyphenyl)prop-2-en-1-one | 110148-86-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-mesityl-1-(4-methoxyphenyl)prop-2-en-1-one
• 英文别名: (E)-1-(4-methoxyphenyl)-3-(2,4,6-trimethylphenyl)prop-2-en-1-one；4'-methoxy-2,4,6-trimethyl-trans-chalcone；4'-Methoxy-2,4,6-trimethyl-trans-chalkon
• CAS: 110148-86-2
• 化学式: C₁₉H₂₀O₂
• 分子量: 280.367
• InChiKey: JPFYXEXJQXQAQV-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-mesityl-1-(4-methoxyphenyl)prop-2-en-1-one 、 二苯基乙炔 在 silver hexafluoroantimonate 、 [RhCp_tCl₂]₂ 、 copper(II) acetate monohydrate 作用下， 以 乙二醇二甲醚 为溶剂， 以81 %的产率得到3-benzoyl-5-methoxy-3-phenyl-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  通过铑 (III) 催化查尔酮与内部炔烃的区域和化学选择性形式 (4+1) 碳环化

  摘要：

  查耳酮通常可以作为苯乙酮的前体，然后通过铑 (III) 催化以区域和化学选择性方式与内部炔烃进行正式 (4+1) 环化。通过该环化形成含有季碳中心的1-茚满酮以及可重复使用的芳基醛。这一发现使得通过苯乙酮与内部炔烃的反应生成茚满酮的实用两步方案成为可能。

  DOI：

  10.1002/anie.202305983
• 作为产物：
  描述：

  2,4,6-三甲基苯甲醛 、 对甲氧基苯乙酮 在 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以70%的产率得到(E)-3-mesityl-1-(4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Solution-phase parallel synthesis of substituted chalcones and their antiparasitary activity against Giardia lamblia

  摘要：

  A library of 25-membered chalcones was prepared by parallel synthesis. Substituted acetophenones and benzaldehydes were condensed using the Claisen-Schmidt base-catalyzed aldol condensation. Several chalcones showed in vitro antiparasitic activity against Giardia lamblia. The highest activity observed for the IC50 values were 12.72, 15.05 and 15.31 mu g/mL, respectively; these are potential leads for the development of antigiardial compounds. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.052

文献信息

• Orchestrating a β-Hydride Elimination Pathway in Palladium(II)-Catalyzed Arylation/Alkenylation of Cyclopropanols Using Organoboron Reagents
  作者：Thangeswaran Ramar、Murugaiah A. M. Subbaiah、Andivelu Ilangovan

  DOI：10.1021/acs.joc.1c02735

  日期：2022.4.1

  scope of chemoselective β-hydride elimination in the context of arylation/alkenylation of homoenolates from cyclopropanol precursors using organoboronic reagents as transmetalation coupling partners was examined. The reaction optimization paradigm revealed a simple ligand-free Pd(II) catalytic system to be most efficient under open air conditions. The preparative scope, which was investigated with

  在使用有机硼试剂作为金属转移偶联剂对环丙醇前体的高烯醇化物进行芳基化/烯基化的情况下，化学选择性 β-氢化物消除的范围进行了研究。反应优化范式揭示了一个简单的无配体 Pd(II) 催化体系在露天条件下最有效。用 48 个例子研究了制备范围，支持该反应适用于广泛的可耐受各种官能团的底物，同时以 62-95% 的产率提供 β-取代的烯酮和二烯酮衍生物。
• A Study of the Direction of Enolization of p-Methoxy-p'-bromodibenzoylmethane and p-Methoxy-p'-ethoxydibenzoylmethane
  作者：R. Percy Barnes、Thomas C. Goodwin、Thomas W. Cotten

  DOI：10.1021/ja01204a059

  日期：1947.12
• Solution-phase parallel synthesis of substituted chalcones and their antiparasitary activity against Giardia lamblia
  作者：Julio Montes-Avila、Sylvia P. Díaz-Camacho、Josefina Sicairos-Félix、Francisco Delgado-Vargas、I.A. Rivero

  DOI：10.1016/j.bmc.2009.02.052

  日期：2009.9

  A library of 25-membered chalcones was prepared by parallel synthesis. Substituted acetophenones and benzaldehydes were condensed using the Claisen-Schmidt base-catalyzed aldol condensation. Several chalcones showed in vitro antiparasitic activity against Giardia lamblia. The highest activity observed for the IC50 values were 12.72, 15.05 and 15.31 mu g/mL, respectively; these are potential leads for the development of antigiardial compounds. (C) 2009 Elsevier Ltd. All rights reserved.
• Regio‐ and Chemoselective Formal (4+1) Carbocyclization of Chalcones with Internal Alkynes via Rhodium(III) Catalysis
  作者：Shuaishuai Song、Yunfei Lai、Zekun Tuo、Jianming Zhong、Wang Zhou

  DOI：10.1002/anie.202305983

  日期：2023.7.24

  Chalcones can unusually serve as the precursors of acetophenones which then undergo formal (4+1) cyclization with internal alkynes via rhodium(III) catalysis in a regio- and chemoselective manner. 1-Indanones containing quaternary carbon centers along with reusable aryl aldehydes were formed by this annulation. This discovery enables a practical two-step protocol to indanones from the reaction of acetophenones

  查耳酮通常可以作为苯乙酮的前体，然后通过铑 (III) 催化以区域和化学选择性方式与内部炔烃进行正式 (4+1) 环化。通过该环化形成含有季碳中心的1-茚满酮以及可重复使用的芳基醛。这一发现使得通过苯乙酮与内部炔烃的反应生成茚满酮的实用两步方案成为可能。