(E)-1-phenyl-3-(3-nitrophenyl)propene

• 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-phenyl-3-(3-nitrophenyl)propene
• 英文别名: (E)-3-(3-nitrophenyl)-1-phenylpropene；(E)-3-(m-nitrophenyl)-1-phenylpropene；3-(3-nitrophenyl)-1-phenylprop-1-ene；1-nitro-3-[(E)-3-phenylprop-2-enyl]benzene
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: XTGYCVVSENHROZ-XBXARRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-acetoxy-2-chloro-3-phenylpropane 以74%的产率得到
  参考文献：
  名称：

  Karpjak W. W., Obushak N. D., Ganushhak N. I., Zh. organ. khimii, 30 (1994) N 11, S 1608-1615

  摘要：

  DOI：

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-coupling reactions of organogold(i) phosphanes with allylic electrophiles
  作者：Miguel Peña-López、Miguel Ayán-Varela、Luis A. Sarandeses、José Pérez Sestelo

  DOI：10.1039/c2ob06788a

  日期：——

  as cinnamyl and geranyl halides (bromide, chloride and acetates) under palladium catalysis in THF at 80 °C to afford the α-substitution product with moderate to high yields. When the reaction is performed with a chiral enantiopure secondary acetate, the α-substituted cross-coupling product is obtained with complete inversion of the stereochemistry.

  芳基和链烯基金（I）膦在钯催化下于80°C在THF中于80°C下与烯丙基亲电试剂如肉桂基和香叶基卤化物（溴化物，氯化物和乙酸盐）发生区域选择性反应，以中等至高收率获得α取代产物。当用手性对映体纯的仲乙酸酯进行反应时，在立体化学完全转化的情况下获得了α-取代的交叉偶联产物。