1,3-dimethoxy-5-(1-(4-methoxyphenyl)vinyl)benzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,3-dimethoxy-5-(1-(4-methoxyphenyl)vinyl)benzene
• 英文别名: 1,3-Dimethoxy-5-[1-(4-methoxyphenyl)ethenyl]benzene；1,3-dimethoxy-5-[1-(4-methoxyphenyl)ethenyl]benzene
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: HVRDFLIGWKVSBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-dimethoxy-5-(1-(4-methoxyphenyl)vinyl)benzene 在 C₃₀H₃₇IrN₂O₃P⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) 、 氢气 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、103.42 kPa 条件下， 反应 15.0h， 以84%的产率得到
  参考文献：
  名称：

  Distinctive Meta-Directing Group Effect for Iridium-Catalyzed 1,1-Diarylalkene Enantioselective Hydrogenation

  摘要：

  An iridium-catalyzed asymmetric hydrogenation of 1,1-diarylkenes is described. Employing a novel, modular phosphoramidite ligand, PhosPrOx, in this transformation affords biologically relevant 1,1-diarylmethine products in good enantiomeric ratios (96.5:3.5 to 71:29). We propose that a meta-directing group, 3,5-dimethoxyphenyl, is responsible for the observed enantioselection, the highest reported, to date, for iridium-catalyzed hydrogenation of 1,1-diarylalkenes lacking ortho-directing groups.

  DOI：

  10.1021/ol303465c
• 作为产物：
  描述：

  1-溴-3,5-二甲氧基苯 在 盐酸 、 magnesium 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 98.17h， 生成 1,3-dimethoxy-5-(1-(4-methoxyphenyl)vinyl)benzene
  参考文献：
  名称：

  Distinctive Meta-Directing Group Effect for Iridium-Catalyzed 1,1-Diarylalkene Enantioselective Hydrogenation

  摘要：

  An iridium-catalyzed asymmetric hydrogenation of 1,1-diarylkenes is described. Employing a novel, modular phosphoramidite ligand, PhosPrOx, in this transformation affords biologically relevant 1,1-diarylmethine products in good enantiomeric ratios (96.5:3.5 to 71:29). We propose that a meta-directing group, 3,5-dimethoxyphenyl, is responsible for the observed enantioselection, the highest reported, to date, for iridium-catalyzed hydrogenation of 1,1-diarylalkenes lacking ortho-directing groups.

  DOI：

  10.1021/ol303465c

文献信息

• Toward a Greener Barluenga–Valdés Cross-Coupling: Microwave-Promoted C–C Bond Formation with a Pd/PEG/H₂O Recyclable Catalytic System
  作者：Diana Lamaa、Estelle Messe、Vincent Gandon、Mouad Alami、Abdallah Hamze

  DOI：10.1021/acs.orglett.9b03310

  日期：2019.11.1

  for the synthesis of 1,1-diarylethylenes using palladium catalysis has been developed. The new catalytic system based on Pd/Xphos–SO3Na or Pd/MeDavephos–CF3SO3 in PEG/H2O under microwave irradiation was found to be the best conditions for this transformation. The recyclability of the palladium catalyst system was also studied, and it was found to be active over nine runs without significant loss in its

  已开发出一种绿色的Barluenga-Valdés交叉偶联反应，利用钯催化合成1,1-二芳基乙烯。发现在微波辐射下，基于PEG / H 2 O中Pd / Xphos-SO 3 Na或Pd / MeDavephos-CF 3 SO 3的新催化体系是该转化的最佳条件。还对钯催化剂体系的可回收性进行了研究，发现钯催化剂体系在九次运行中均具有活性，而活性没有明显损失。
• Synthesis of methylated resveratrol and analogues by Heck reactions in organic and aqueous solvents
  作者：Luis Botella、Carmen Nájera

  DOI：10.1016/j.tet.2004.04.076

  日期：2004.6

  methodology for the synthesis of methoxylated (E)-stilbene derivatives. Couplings can be performed either with (dicyclohexyl)methylamine as base and TBAB in aqueous DMA or in neat water and with Et3N as base in DMA in air and under thermal and microwave conditions. The arylation of different styrenes are performed with 3,5-dimethoxyiodobenzene to afford a series of important biologically active (E)-stilbene

  在无膦条件下，使用肟衍生的四环四环或Pd（OAc）2作为催化剂的Heck反应是合成甲氧基化（E）-二苯乙烯衍生物的一般方法。可以在空气中或在热和微波条件下，以（二环己基）甲胺为碱，TBAB在DMA水溶液中或在纯水中，以Et 3 N为碱，在DMA中进行偶合。用3,5-二甲氧基碘苯进行不同苯乙烯的芳基化反应，得到一系列重要的具有3,5-二甲氧基苯基部分的重要生物活性（E）-二苯乙烯衍生物，包括白藜芦醇，甲基邻苯三酚和品脱甲硅烷基，这些衍生物可以高区域选择性地有效制备。和总立体选择性（TON高达104）。
• An expedient synthesis of resveratrol through a highly recoverable palladium catalyst
  作者：Alejandro V. Martínez、José I. García、José A. Mayoral

  DOI：10.1016/j.tet.2016.08.074

  日期：2017.9

  range of 75–80%. The key synthetic step, a Heck–Mizoroki CC cross-coupling reaction, is efficiently promoted by a heterogeneous catalyst consisting of palladium nanoparticles supported on synthetic clay. This solid catalyst is quite handy and displays high stability and robustness under reaction conditions. The catalyst can be easily recovered and reused at least 10 times, which improves the overall

  描述了一种简单的两步合成白藜芦醇，总分离产率为75-80％。关键的合成步骤，即Heck-Mizoroki C C交叉偶联反应，是由负载在合成粘土上的钯纳米颗粒组成的非均相催化剂有效地促进的。这种固体催化剂非常方便，在反应条件下显示出很高的稳定性和鲁棒性。催化剂可以轻松回收并至少重复使用10次，从而提高了系统的总体催化效率。而且，溶剂的使用受到限制，并且反应程序允许所需产物的简便分离和纯化，而没有伴随的离子副产物和钯污染。
• Diversity-Oriented Synthesis of Disubstituted Alkenes Using Masked Silanols
  作者：Hannah F. Sore、David T. Blackwell、Simon J. F. MacDonald、David R. Spring

  DOI：10.1021/ol100895d

  日期：2010.6.18

  The regio- and stereoselective synthesis and subsequent Hiyama cross coupling of pentafluorophenyldimethylvinylsilanes has been developed, thus providing a convenient and robust method for the diversity-oriented synthesis of (E)-, (Z)- and alpha-disubstituted alkenes from terminal alkynes. Pentafluorophenyldimethylvinylsilanes undergo cross-coupling reactions with excellent selectivity and in good yields, offering an attractive alternative to existing masked silanols.
• Distinctive <i>Meta</i>-Directing Group Effect for Iridium-Catalyzed 1,1-Diarylalkene Enantioselective Hydrogenation
  作者：Elizabeth N. Bess、Matthew S. Sigman

  DOI：10.1021/ol303465c

  日期：2013.2.1

  An iridium-catalyzed asymmetric hydrogenation of 1,1-diarylkenes is described. Employing a novel, modular phosphoramidite ligand, PhosPrOx, in this transformation affords biologically relevant 1,1-diarylmethine products in good enantiomeric ratios (96.5:3.5 to 71:29). We propose that a meta-directing group, 3,5-dimethoxyphenyl, is responsible for the observed enantioselection, the highest reported, to date, for iridium-catalyzed hydrogenation of 1,1-diarylalkenes lacking ortho-directing groups.