(E)-3-[(4-N,N-dimethylaminophenyl)]-1-phenylpropene

• 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-[(4-N,N-dimethylaminophenyl)]-1-phenylpropene
• 英文别名: 4-cinnamyl-N,N-dimethylaniline；N,N-dimethyl-4-[(E)-3-phenylprop-2-enyl]aniline
• 化学式: C₁₇H₁₉N
• 分子量: 237.345
• InChiKey: RIYWPIYVUDBWSV-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-(N,N-二甲基)苯胺溴化镁 在 [Ni(Cl){N-(2-Ph₂PC₆H₄)(2′-Me₂NC₆H₄)}] 、 lithium chloride 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 生成 (E)-3-[(4-N,N-dimethylaminophenyl)]-1-phenylpropene
  参考文献：
  名称：

  Pincer-Nickel-Catalyzed Allyl-Aryl Coupling between Allyl Methyl Ethers and Arylzinc Chlorides

  摘要：

  The P,N,N-pincer nickel complex [Ni(C1l)-(N-(2-Ph2PC6H4)(2'-Me2NC6H4)}]-catalyzed allyl-aryl coupling was studied. The reaction of ally! methyl ethers, including (1-methoxyallyl)arenes and (3-methoxyprop-1-en-1-yl)arenes, with arylzinc chlorides afforded linear (E)-alkenes in high yields, whereas the reaction of (E)-1-methoxytridec-2-ene with p-Me2NC6H4ZnCl generated a mixture of linear and branched alkenes.

  DOI：

  10.1021/acs.joc.5b02151

文献信息

• A Transition-Metal-Free Cross-Coupling Reaction of Allylic Bromides with Aryl- and Vinylboronic Acids
  作者：Mitsuhiro Ueda、Ilhyong Ryu、Kota Nishimura、Ryo Kashima

  DOI：10.1055/s-0031-1290656

  日期：2012.4

  A cross-coupling reaction between aryl- and vinylboronic acids and various allylic bromides proceeded without the use of a transition-metal catalyst to give the corresponding allylated products in moderate to good yields. The use of an inorganic base (KF or Cs2CO3) and a small amount of water is crucial in obtaining good performance in the present transition-metal-free reaction. transition-metal-free

  在不使用过渡金属催化剂的情况下，进行了芳基和乙烯基硼酸与各种烯丙基溴之间的交叉偶联反应，以中等至良好的产率得到了相应的烯丙基化产物。在目前的无过渡金属反应中，使用无机碱（KF或Cs 2 CO 3）和少量水对于获得良好的性能至关重要。 无过渡金属-CC键形成-芳基和乙烯基硼酸
• 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。
• Iron-Catalyzed Allylic Arylation of Olefins via C(sp³)–H Activation under Mild Conditions
  作者：Masaki Sekine、Laurean Ilies、Eiichi Nakamura

  DOI：10.1021/ol400056z

  日期：2013.2.1

  cycloalkene or an allylbenzene derivative into a C–C bond in the presence of a catalytic amount of Fe(acac)3 and a diphosphine ligand at 0 °C. The stereo- and regioselectivity of the reaction, together with deuterium labeling experiments, suggest that C–H bond activation is the slow step in the catalytic cycle preceding the formation of an allyliron intermediate.

  芳基碘化物存在下的芳基格氏试剂可在催化量的Fe（acac）3和二膦配体在0°存在的情况下将环烯烃或烯丙基苯衍生物的烯丙基C–H键转换为C–C键C。反应的立体选择性和区域选择性，以及氘标记实验表明，CH键的活化是烯丙基铁中间体形成之前催化循环的缓慢步骤。
• Organic anions. Part 1. Equilibration of 1,3-diarylpropenes
  作者：Richard J. Bushby、Gerald J. Ferber

  DOI：10.1039/p29760001683

  日期：——

  A number of 1,3-diarylpropenes, potential precursors of the allylic anions (I). have been synthesised, and the base catalysed equilibration between the double bond isomers (II) and (III) has been investigated. The equilibrium constants correlate satisfactorily with the substituent constant σ. N.m.r. shift reagents aided spectroscopic analysis of certain mixtures.

  许多1,3-二芳基丙烯，烯丙基阴离子（I）的潜在前体。已合成，并且研究了双键异构体（II）和（III）之间的碱催化平衡。平衡常数与取代基常数σ令人满意地相关。Nmr变换试剂有助于某些混合物的光谱分析。
• Nickel-Catalyzed Cross-Coupling of Allyl Alcohols with Aryl- or Alkenylzinc Reagents
  作者：Bo Yang、Zhong-Xia Wang

  DOI：10.1021/acs.joc.6b02564

  日期：2017.5.5

  Nickel-catalyzed cross-coupling of allyl alcohols with aryl- and alkenylzinc chlorides through C–O bond cleavage was performed. Reaction of (E)-3-phenylprop-2-en-1-ol and 1-aryl-prop-2-en-1-ols with aryl- or alkenylzinc chlorides gave linear cross-coupling products. Reaction of 1-phenyl- or 1-methyl-substituted (E)-3-phenylprop-2-en-1-ol with aryl- or alkenylzinc chlorides resulted in 3-aryl/alkenyl-substituted

  进行了镍醇与烯丙基氯化锌和烯基氯化锌通过C–O键裂解的镍催化交叉偶联反应。（E）-3-苯基丙-2-烯-1-醇和1-芳基丙-2-烯-1-醇与芳基或烯基氯化锌的反应得到线性交叉偶联产物。1-苯基或1-甲基取代的（E）-3-苯基丙-2-烯-1-醇与芳基或烯基氯化锌的反应生成3-芳基/烯基取代的（E）-（prop-1 -烯-1，3-二基）二苯或3-芳基/烯基取代的（E）-（丁-1-烯基）苯。烯丙醇与p -Me 2 NC 6 H 4 ZnCl的反应生成正常偶联产物4-烯丙基-N，N的混合物-二甲基苯胺及其异构化产物N，N-二甲基-4-（丙-1-烯-1-基）苯胺。