(E)-1-[4-(hex-1-enyl)phenyl]ethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1-[4-(hex-1-enyl)phenyl]ethanone
• 英文别名: 1-[4-[(E)-hex-1-enyl]phenyl]ethanone
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: BWEPZNANRIFTAF-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  反式-1-己烯-1-基硼酸 在 potassium phosphate monohydrate 、 palladium diacetate 、 三环己基膦 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 1.33h， 生成 (E)-1-[4-(hex-1-enyl)phenyl]ethanone
  参考文献：
  名称：

  Microwave-assisted Suzuki–Miyaura cross-coupling of 2-alkyl and 2-alkenyl-benzo-1,3,2-diazaborolanes

  摘要：

  Nitrogen-based boronate esters, such as 2-octyl-benzo-1,3,2-diazaborolane, 2-phenethyl-benzo-1,3,2-diazaborolane, and 2-{(1E)-hexenyl}-benzo-1,3,2-diazaborolane have been shown to be suitable coupling partners with arylhalides in microwave accelerated Suzuki cross-coupling reactions. Reaction yields of up to 89% were achieved. The use of a silicon group attached to the nitrogen atom, proved to enhance the reactivity of 2-octyl-benzo-1,3,2-diazaborolane. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.095

文献信息

• Palladium-Catalyzed Desulfitative Mizoroki-Heck Couplings of Sulfonyl Chlorides with Mono- and Disubstituted Olefins: Rhodium-Catalyzed Desulfitative Heck-Type Reactions under Phosphine- and Base-Free Conditions
  作者：Srinivas Reddy Dubbaka、Pierre Vogel

  DOI：10.1002/chem.200400838

  日期：2005.4.22

  olefins with arenesulfonyl and trifluoromethanesulfonyl chlorides. Thus (E)-1,2-disubstituted alkenes with high stereoselectivity and 1,1,2-disubstituted alkenes with 12:1 to 21:1 E/Z steroselectivity can be obtained. Herrmann's palladacycle at 0.1 mol % is sufficient to catalyze these reactions, for which electron-rich or electron-poor sulfonyl chlorides and alkenes are suitable. If phosphine- and base-free

  已经发现了新的条件，用于用芳烃磺酰氯和三氟甲烷磺酰氯对单取代和无取代的烯烃进行脱硫的Mizoroki-Heck芳基化和三氟甲基化。因此，可以获得具有高立体选择性的（E）-1,2-二取代的烯烃和具有12：1至21：1的E / Z立体选择性的1,1,2-二取代的烯烃。0.1摩尔％的赫尔曼（Hermann）的Palladacycle足以催化这些反应，对此，富电子或贫电子的磺酰氯和烯烃是合适的。如果需要无磷和无碱条件，则1摩尔％[RhCl（C（2）H（4））（2）]催化脱硫交叉偶联反应。与报道的[RuCl（2）（PPh（3））（2）]催化与磺酰氯偶联反应的结果相反，自由基清除剂不会抑制钯和铑的脱硫Mizoroki-Heck偶联反应。在Pd或Rh催化剂的存在下，在更高的温度下，烯烃在60摄氏度下磺酰化产生的可能的砜不会被脱硫。
• Highly Active Catalyst for the Heterogeneous Suzuki−Miyaura Reaction:  Assembled Complex of Palladium and Non-Cross-Linked Amphiphilic Polymer
  作者：Yoichi M. A. Yamada、Koji Takeda、Hideyo Takahashi、Shiro Ikegami

  DOI：10.1021/jo034354v

  日期：2003.10.1

  An assembled insoluble catalyst, PdAS, prepared from palladium ((NH4)2PdCl4 (1)) and non-cross-linked amphiphilic copolymer poly(N-isopropylacrylamide-co-4-diphenylstyrylphosphine) (2) was developed. It was found that PdAS is an excellent catalyst for the Suzuki-Miyaura reaction on three points: (1) The use of 8 x 10(-7) to 5 x 10(-4) mol equiv of PdAS afforded the coupling products efficiently after

  开发了由钯（（NH4）2PdCl4（1））和非交联两亲共聚物聚（N-异丙基丙烯酰胺-co-4-二苯基苯乙烯基膦）（2）制备的组装的不溶催化剂PdAS。已发现，PdAS在以下三个方面是铃木-宫浦反应的优良催化剂：（1）使用8 x 10（-7）到5 x 10（-4）摩尔当量的PdAS在偶联后有效地提供了偶联产物简单的后处理，营业额高达1,250,000。（2）催化剂可重复使用多次而不会损失催化活性。（3）PdAS在任何反应介质（即水或水性或无水有机溶剂）中均显示出良好的稳定性。对PdAS的分析研究表明2中的膦与钯配位形成PdCl2（PPh2Ar）2物种。
• A Versatile Catalyst for Heck Reactions of Aryl Chlorides and Aryl Bromides under Mild Conditions
  作者：Adam F. Littke、Gregory C. Fu

  DOI：10.1021/ja010988c

  日期：2001.7.1

  for Heck reactions of aryl chlorides and bromides. A sterically and electronically diverse array of aryl bromides, as well as activated aryl chlorides, couple with a range of mono- and disubstituted olefins at room temperature, furnishing the arylated product with high E/Z stereoselection. The corresponding reactions of a broad spectrum of electron-neutral and electron-rich aryl chlorides proceed at

  在 Cy2NMe 存在下，Pd/P(t-Bu)3 可作为一种非常温和且用途广泛的催化剂，用于芳基氯化物和溴化物的 Heck 反应。空间和电子上不同的芳基溴化物阵列以及活化的芳基氯化物，在室温下与一系列单取代和双取代的烯烃偶联，为芳基化产物提供高 E/Z 立体选择。广泛的电子中性和富电子芳基氯化物的相应反应在升高的温度下进行，并且具有高选择性。在范围和温和性方面，Pd/P(t-Bu)3/Cy2NMe 代表了先前报道的这些 Heck 偶联过程的催化剂的进步。
• Palladium Complexes with N,<scp>O‐Bidentate</scp> Ligands Based on <scp><i>N</i>‐Oxide</scp> Units from Cyclic Secondary Amines: Synthesis and Catalytic Application in <scp>Mizoroki‐Heck</scp> Reaction
  作者：Xuefeng Jia、Yanyan Wen、Changhui He、Xianqiang Huang

  DOI：10.1002/cjoc.202300375

  日期：2024.2

  ions were presented as counter anions in complex II. But the palladium(II) center of IV was coordinated by nitrogen and oxygen atoms from one ligand (L4) as well as two chlorine atoms, which exhibited the nearly square-planar geometry. The study on catalytic properties of palladium complexes revealed that complex II exhibited high activity superior to the other complexes. The coupling reactions of

  钯催化的 Mizoroki-Heck 反应是构建 C sp2 –C sp2键的强大而有效的方法。本文轻松合成了四种基于环状仲胺N-氧化物单元的带有 N,O-二齿配体 ( L 1 - L 4 ) 的钯配合物 ( I — IV ) ，并成功应用于芳基溴与电子的 Mizoroki-Heck 反应-缺乏的烯烃。X射线衍射分析表明II的钯(II)原子具有扭曲的正方形平面几何形状，并且由来自两个配体( L 2 )的氮和氧原子进行四配位。配合物II中存在两个游离氯离子作为抗衡阴离子。但IV的钯(II)中心由一个配体( L 4 )的氮原子和氧原子以及两个氯原子配位，呈现出接近正方形的平面几何形状。对钯配合物催化性能的研究表明，配合物II表现出优于其他配合物的高活性。一系列芳基溴和烯烃衍生物的偶联反应在2-5 mol%钯配合物II存在下进行，以良好至优异的产率得到所需产物。该方法具有官能团相容性好、产率高、
• A Reassessment of the Transition-Metal Free Suzuki-Type Coupling Methodology
  作者：Riina K. Arvela、Nicholas E. Leadbeater、Michael S. Sangi、Victoria A. Williams、Patricia Granados、Robert D. Singer

  DOI：10.1021/jo048531j

  日期：2005.1.1

  We present here a reassessment of our transition-metal free Suzuki-type coupling protocol. We believe that, although the reaction can be run without the need for addition of a metal catalyst, palladium contaminants down to a level of 50 ppb found in commercially available sodium carbonate are responsible for the generation of the biaryl rather than, as previously suggested, an alternative non-palladium-mediated pathway. We present a revised methodology for Suzuki couplings using ultralow palladium concentrations for use with aryl and vinyl boronic acids and discuss the effects of the purity of the boronic acid on the reaction.