1-butoxy-1,2-diphenylethene

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-butoxy-1,2-diphenylethene
• 英文别名: [(Z)-1-butoxy-2-phenylethenyl]benzene
• 化学式: C₁₈H₂₀O
• 分子量: 252.356
• InChiKey: LLZQVZFTDXCNKN-SDXDJHTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 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：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二苯基乙酮 、 甲磺酸正丁酯 在 氢氧化钾 、 PHDB₁₈C₆ 作用下， 以 苯 为溶剂， 反应 20.0h， 以74%的产率得到1-butoxy-1,2-diphenylethene
  参考文献：
  名称：

  Macrocyclic Polyethers as Enolate Activators in Base-Catalyzed Phase-Transfer Reactions

  摘要：

  A kinetic study of the alkylation reaction of deoxybenzoin (1) with alkylating agents 2-4, catalyzed by PHDB18C6 7 or [2.2.2,C-10]cryptand 8, has been performed in chlorobenzene-aqueous (or solid) base (NaOH, KOH) two-phase systems, under liquid-liquid (LL) and solid-liquid (SL) phase-transfer catalysis (PTC) conditions. The results obtained seem to indicate a multistep mechanism where the Ligand transfers the enolate from the interface to the bulk organic phase and the alkylation reaction is rate determining for all the process. The enolate reactivity strongly depends on the ligand and, to a lesser extent, on the base. The highest rate constant values are obtained under SL-PTC conditions and with [2.2.2,C-10]cryptand 8,which realizes the best cation-anion separation and hence anion activation. In line with these data, UV-vis spectroscopic determinations of the complexed enolate (M(+)subset of Lig)R- exhibit bathochromic shifts of the absorption maximum wavelength (lambda(max)) on changing from crown ether to cryptand. The distribution of the reaction products (O/C alkylation ratio) is also related to the different ability of the ligand to separate cation from anion in the ion pair.

  DOI：

  10.1021/jo9801216

文献信息

• Regio- and Stereoselective Intermolecular Hydroalkoxylation of Alkynes Catalysed by Cationic Gold(I) Complexes
  作者：Avelino Corma、Violeta R. Ruiz、Antonio Leyva-Pérez、María J. Sabater

  DOI：10.1002/adsc.201000094

  日期：——

  levels of stereoselectivity by using cationic gold(I)‐phosphine complexes as catalysts. By choosing the appropriate phosphine, the selective formation of the Z or the E isomer of the vinyl ether can be tuned, and the undesired formation of the ketal can be controlled. The isomerisation of fumarates (Z‐isomer) to maleates (E‐isomer) is a gold‐catalysed process that can be conducted in one‐pot. When

  乙烯基醚和缩酮是通过使用阳离子金（I）-膦配合物作为催化剂，以良好的收率和立体选择性水平从苯乙炔衍生物和乙炔二羧酸二甲酯（DMAD）与醇反应制得的。通过选择合适的膦，可以调节乙烯基醚的Z或E异构体的选择性形成，并且可以控制缩酮的不期望的形成。富马酸酯（Z-异构体）到马来酸酯（E-异构体）的异构化是金催化的过程，可以在一个罐中进行。当使用多元醇时，通过用己烷萃取很容易将五元环状缩酮分离出来，并且金的络合物可以重复使用。
• Iron(III) Triflimide as a Catalytic Substitute for Gold(I) in Hydroaddition Reactions to Unsaturated Carbon-Carbon Bonds
  作者：Jose R. Cabrero-Antonino、Antonio Leyva-Pérez、Avelino Corma

  DOI：10.1002/chem.201300386

  日期：2013.6.24

  In this work it is shown that iron(III) and gold(I) triflimide efficiently catalyze the hydroaddition of a wide array of nucleophiles including water, alcohols, thiols, amines, alkynes, and alkenes to multiple CC bonds. The study of the catalytic activity and selectivity of iron(III), gold(I), and Brønsted triflimides has unveiled that iron(III) triflimide [Fe(NTf2)3] is a robust catalyst under heating

  在这项工作中表明，三氟甲磺酸铁（III）和金（I）可有效催化多种亲核试剂（包括水，醇，硫醇，胺，炔烃和烯烃）加氢成多个CC键。铁（III），金（I）和布朗斯台德三氟甲酸酯的催化活性和选择性的研究表明，三氟甲铁（III）[Fe（NTf 2）3 ]在加热条件下是一种坚固的催化剂，而金（I） ）甚至由PPh 3稳定的三氟甲酰亚胺在80°C时容易分解并释放出三氟乙二酸（HNTf 2），该三氟乙二酸可催化相应的反应，如原位19 F，15 N和311 H NMR光谱。此处给出的结果表明，两种催化剂类型均具有弱点和优势，并且彼此互补。三氟化铁（III）可以替代三氟化金（I），作为不饱和碳-碳键加氢反应的催化剂。
• Stereoselective Gold(I)-Catalyzed Intermolecular Hydroalkoxlation of Alkynes
  作者：Richard M. P. Veenboer、Stéphanie Dupuy、Steven P. Nolan

  DOI：10.1021/cs501976s

  日期：2015.2.6

  We report the use of cationic gold complexes [Au(NHC)(CH3CN)][BF4] and [Au(NHC)}2(μ–OH)][BF4] (NHC = N-heterocyclic carbene) as highly active catalysts in the solvent-free hydroalkoxylation of internal alkynes using primary and secondary alcohols. Using this simple protocol, a broad range of (Z)-vinyl ethers were obtained in excellent yields and high stereoselectivities. The methodology allows for

  我们报道了阳离子金络合物[Au（NHC）（CH 3 CN）] [BF 4 ]和[Au（NHC）} 2（μ–OH）] [BF 4 ]的使用（NHC = N杂环卡宾）作为使用伯醇和仲醇的内部炔烃的无溶剂加氢烷氧基化反应中的高活性催化剂。使用此简单的协议，以优异的产率和高的立体选择性获得了广泛的（Z）乙烯基醚。该方法允许使用低至200 ppm的催化剂负载量，以向内部炔烃中添加伯醇（TON = 35 000，TOF = 2188 h –1）。