(E)-1-[p-(3-phenyl-allyl)phenyl]ethanone

• 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)-1-[p-(3-phenyl-allyl)phenyl]ethanone
• 英文别名: (E)-1-[p-(3-phenylallyl)phenyl]ethanone；(E)-3-(4-acetylphenyl)-1-phenylpropene；1-[4-[(E)-3-phenylprop-2-enyl]phenyl]ethanone
• 化学式: C₁₇H₁₆O
• 分子量: 236.313
• InChiKey: YSRIJWJVHAEECM-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(cinnamyloxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 三乙烯二胺 、 乙二醇二甲醚溴化镍 、 2,4,5,6-四(9H-咔唑-9-基)异酞腈 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成 (E)-1-[p-(3-phenyl-allyl)phenyl]ethanone
  参考文献：
  名称：

  三氟硼酸烯丙酯与芳基卤化物的光氧化还原/镍双催化区域选择性烯丙基芳基化反应

  摘要：

  已经开发出一种高效的三氟硼酸烯丙酯与芳基卤化物的光氧化还原/镍双催化偶联反应，为多种取代的烯丙基苯提供了一条有吸引力的途径。该方法具有高效和区域选择性、温和的反应条件、广泛的底物范围和官能团相容性等优点。机理研究表明，通过向镍物种中添加烯丙基自由基生成的 π-烯丙基镍 (III) 中间体可能是关键反应中间体。

  DOI：

  10.1021/acs.orglett.3c01147

文献信息

• Palladium(0)-catalyzed direct cross-coupling reaction of allylic alcohols with aryl- and alkenylboronic acids
  作者：Hirokazu Tsukamoto、Tomomi Uchiyama、Takamichi Suzuki、Yoshinori Kondo

  DOI：10.1039/b804991b

  日期：——

  Allylic alcohols can be used directly for the palladium(0)-catalyzed allylation of aryl- and alkenylboronic acids with a wide variety of functional groups. A triphenylphosphine-ligated palladium catalyst turns out to be most effective for the cross-coupling reaction and its low loading (less than 1 mol%) leads to formation of the coupling product in high yield. The Lewis acidity of the organoboron

  烯丙醇可直接用于钯（0）催化的具有多种官能团的芳基和烯基硼酸的烯丙基化。事实证明，三苯基膦连接的钯催化剂对于交叉偶联反应是最有效的，并且其低载量（小于1mol％）导致以高收率形成偶联产物。有机硼试剂的路易斯酸度和较弱的羟基离去能力（高碱性）对于交叉偶联反应至关重要。该反应过程是原子经济且对环境无害的，因为它既不需要制备烯丙基卤和酯，也不需要添加化学计量的碱。此外，含有另一个不饱和碳-碳键的烯丙基醇经历芳基化环化反应，导致形成环戊烷。
• Palladium(0)-catalyzed direct cross-coupling reaction of allyl alcohols with aryl- and vinyl-boronic acidsElectronic supplementary information (ESI) available: spectral data of compounds. See http://www.rsc.org/suppdata/cc/b4/b402256d/
  作者：Hirokazu Tsukamoto、Masanori Sato、Yoshinori Kondo

  DOI：10.1039/b402256d

  日期：——

  Allyl alcohols can be directly used for the palladium-catalyzed allylation of aryl- and vinyl-boronic acids without the aid of a base.

  烯丙醇可直接用于芳基硼酸和乙烯基硼酸的钯催化烯丙基化，无需碱的帮助。
• A Novel Palladium Catalyst for Cross-Coupling of Allyl Acetates with Arylboronic Acids
  作者：Didier Bouyssi、Vincent Gerusz、Geneviève Balme

  DOI：10.1002/1099-0690(200208)2002:15<2445::aid-ejoc2445>3.0.co;2-s

  日期：2002.8

  The palladium-catalyzed coupling reactions of various arylboronic acids and allylic acetates take place readily under mild conditions. The choice of ligand in the palladium catalyst and the solvent are critical to the yields of coupled products.(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

  各种芳基硼酸和烯丙基乙酸酯的钯催化偶联反应在温和条件下容易发生。钯催化剂中配体和溶剂的选择对偶联产物的产率至关重要。 (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
• Palladium-catalyzed cross-couplings of allylic phosphates
  作者：Veselin Maslak、Zorana Tokic-Vujosevic、Radomir N. Saicic

  DOI：10.1016/j.tetlet.2009.02.026

  日期：2009.4

  A range of palladium-catalyzed cross-coupling reactions can be performed using allylic phosphates as electrophiles. Both conventional heating and microwave irradiation can be used. (C) 2009 Elsevier Ltd. All rights reserved.
• Selective Cross-Coupling of Organic Halides with Allylic Acetates
  作者：Lukiana L. Anka-Lufford、Michael R. Prinsell、Daniel J. Weix

  DOI：10.1021/jo302086g

  日期：2012.11.16

  A general protocol for the coupling of haloarenes with a variety of allylic acetates is presented. Strengths of the method are a tolerance for electrophilic (ketone, aldehyde) and acidic (sulfonamide, trifluoroacetamide) substrates and the ability to couple with a variety of substituted allylic acetates. Secondary alkyl bromides can also be allylated under slightly modified conditions, demonstrating the generality of the approach. Finally, the coupling of a reactive vinyl halide could be achieved by the use of a very hindered ligand and more reactive, branched allylic acetates.