3-(4-acetylphenyl)-1-(4-methoxyphenyl)propan-1-one | 1334709-37-3

• 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: 3-(4-acetylphenyl)-1-(4-methoxyphenyl)propan-1-one
• 英文别名: 3-(4-Acetylphenyl)-1-(4-methoxyphenyl)propan-1-one
• CAS: 1334709-37-3
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: NUFDWHOVAVTORD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-溴苯乙酮 在 四氢吡咯 、 N-甲基二环己基胺 、 potassium carbonate 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 2-二叔丁基膦-1-苯基吲哚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 3-(4-acetylphenyl)-1-(4-methoxyphenyl)propan-1-one
  参考文献：
  名称：

  Double Arylation of Allyl Alcohol via a One-Pot Heck Arylation–Isomerization–Acylation Cascade

  摘要：

  A one-pot, two-step catalytic protocol has been developed. A regloselective Heck coupling between aryl bromides and allyl alcohol leads to the generation of arylated allyl alcohols that in situ isomerize to give aldehydes, which then undergo an acylation reaction with a second aryl bromide. A variety of aryl bromides can be employed in both the initial Heck reaction and the acylation, providing easy access to a wide variety of substituted dihydrochalcones.

  DOI：

  10.1021/ol202144z

文献信息

• Remote Nickel-Catalyzed Cross-Coupling Arylation via Proton-Coupled Electron Transfer-Enabled C–C Bond Cleavage
  作者：Long Huang、Tengfei Ji、Magnus Rueping

  DOI：10.1021/jacs.9b12490

  日期：2020.2.19

  carbon-carbon bond activation is still rather underdeveloped due to the bond inertness. Herein, we report a mild and general strategy for the activation of a diverse set of readily available cyclic alcohols for the remote and site-specific arylation of ketones via the combination of photoredox-mediated multisite concerted proton-electron transfer (MS-PCET) and nickel catalysis. The current cross-coupling proceeds

  碳-碳和碳-杂原子键形成的交叉偶联反应在现代化学合成中具有重要意义。除了涉及预先形成或预先激活的偶联伙伴的经典交叉偶联外，最近在使用氢原子转移反应选择性、直接偶联丰富的脂肪族碳氢键方面取得了突破，其中键离解能是热力学驱动力. 由于键惰性，更具挑战性的碳-碳键活化仍然相当不发达。在此处，我们报告了一种温和而通用的策略，用于通过光氧化还原介导的多位点协调质子电子转移 (MS-PCET) 和镍催化的组合，激活多种易于获得的环醇，用于酮的远程和位点特异性芳基化. 当前的交叉偶联随着使用键解离自由能 (BDFE) 作为热力学驱动力的烷氧基的产生而进行。随后，由 CC 裂解形成的远程碳中心自由基与镍催化循环合并，形成具有挑战性的 C(sp3)-C(sp2) 键。
• Ligated Regioselective PdII Catalysis to Access β-Aryl-Bearing Aldehydes, Ketones, and β-Keto Esters
  作者：Mari Vellakkaran、Murugaiah M. S. Andappan、Nagaiah Kommu

  DOI：10.1002/ejoc.201200770

  日期：2012.9

  arylative isomerization of allyl alcohols, a milder and regioselective access to the versatile building blocks β-aryl aldehydes and ketones was developed. This new and chelation-controlled protocol enabled the compatibility of wide range of functionalities to generate dihydrochalcones, α-benzyl-α′-alkyl acetones, dihydrocinnamaldehydes, and α-benzyl β-keto esters (from Baylis–Hillman adducts). A practical

  通过在 PdII 介导的烯丙醇芳基化异构化中使用配体，开发了一种更温和和区域选择性的通用构建块 β-芳基醛和酮。这种新的螯合控制方案使广泛的功能兼容，以生成二氢查耳酮、α-苄基-α'-烷基丙酮、二氢肉桂醛和 α-苄基 β-酮酯（来自 Baylis-Hillman 加合物）。还展示了普罗帕酮中间体的实用多克合成。
• Double Arylation of Allyl Alcohol via a One-Pot Heck Arylation–Isomerization–Acylation Cascade
  作者：Paul Colbon、Jiwu Ruan、Mark Purdie、Keith Mulholland、Jianliang Xiao

  DOI：10.1021/ol202144z

  日期：2011.10.21

  A one-pot, two-step catalytic protocol has been developed. A regloselective Heck coupling between aryl bromides and allyl alcohol leads to the generation of arylated allyl alcohols that in situ isomerize to give aldehydes, which then undergo an acylation reaction with a second aryl bromide. A variety of aryl bromides can be employed in both the initial Heck reaction and the acylation, providing easy access to a wide variety of substituted dihydrochalcones.