2-对氯苯基-3-甲基-2-丁烯 | 28094-82-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-对氯苯基-3-甲基-2-丁烯
• 英文名称: 1-chloro-4-(3-methylbut-2-en-2-yl)benzene
• CAS: 28094-82-8
• 化学式: C₁₁H₁₃Cl
• 分子量: 180.677
• InChiKey: WDMQBLWCCZXOLN-UHFFFAOYSA-N

物化性质

• 沸点：
  91-94 °C(Press: 6 Torr)
• 密度：
  1.011±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-对氯苯基-3-甲基-2-丁烯 、 氰化亚铜 以 喹啉 为溶剂， 生成 2-Methyl-3-p-cyanophenyl-2-buten
  参考文献：
  名称：

  Chemistry of singlet oxygen. XII. Electronic effects on rate and products of the reaction with olefins

  摘要：

  DOI：

  10.1021/ja00749a032
• 作为产物：
  描述：

  3-(4-chlorophenyl)-2,2-dimethylbut-3-enoic acid 生成 2-对氯苯基-3-甲基-2-丁烯
  参考文献：
  名称：

  脱羧研究。第六部分 β-酮酸和βγ-不饱和酸脱羧过渡态的比较

  摘要：

  将取代基对β- γ-不饱和酸的热脱羧速率的影响与其对β-酮酸的脱羧的影响进行比较。从观察到的相似性来看，认为反应具有几乎相同的过渡态。已经证明，烯酸的过渡态在很大程度上是非极性的。通过类推，得出酮酸通过很大程度上非极性的机理脱羧。关于β-酮酸脱羧的更早的论点得到了严格的审查。

  DOI：

  10.1039/j29680000436

文献信息

• Silver‐Catalysed Hydroarylation of Highly Substituted Styrenes
  作者：Toryn Dalton、Steffen Greßies、Mowpriya Das、Maximilian Niehues、Malte L. Schrader、Christian Gutheil、Bart Jan Ravoo、Frank Glorius

  DOI：10.1002/anie.202016268

  日期：2021.4.6

  Hydroarylation is an effective strategy to rapidly increase the complexity of organic structures by transforming flat alkene moieties into three‐dimensional frameworks. Many strategies have already been developed to achieve the hydroarylation of styrenes, however most of these reports examine the hydroarylation of unpolar, β‐mono‐ or β‐unsubstituted styrenes, while exploring mainly electron‐rich benzene

  加氢芳基化是一种有效的策略，可通过将平面烯烃部分转化为三维框架来快速增加有机结构的复杂性。已经开发出许多策略来实现苯乙烯的加氢芳基化，然而，大多数这些报告在主要研究富含电子的苯亲核试剂的同时，研究了非极性，β-单取代或β-未取代的苯乙烯的加氢芳基化。在本文中，我们报道了一种温和而通用的催化体系，用于多取代苯乙烯和杂芳族苯乙烯的选择性加氢杂芳基化。反应的机理分析导致发现了市售的2,2'：5'，2''-噻吩作为关键试剂。
• Highly Stereoselective Positional Isomerization of Styrenes <i>via</i> <scp>Acid‐Catalyzed</scp> Carbocation Mechanism
  作者：Xiao‐Si Hu、Jun‐Xiong He、Ying Zhang、Jian Zhou、Jin‐Sheng Yu

  DOI：10.1002/cjoc.202100218

  日期：2021.8

  The first transition metal-free highly stereoselective positional isomerization of various α-alkyl styrenes through a carbocation mechanism triggered strategy is developed by using Al(OTf)3 as a hidden Brønsted acid catalyst, which provides facile access to value-added acyclic tri- and tetra-substituted alkenes in good yields with high stereoselectivity under mild conditions. The practicality of this

  通过使用 Al(OTf) 3作为隐藏的 Brønsted 酸催化剂，通过碳阳离子机制触发的策略开发了第一个无过渡金属的各种 α-烷基苯乙烯的高度立体选择性位置异构化，这为获得增值的无环三-和在温和条件下以高立体选择性和高收率制备四取代烯烃。该协议的实用性由克级合成、高立体选择性、良好的官能团耐受性和简单的操作进一步突出。机理研究支持 Al(OTf) 3充当隐藏的布朗斯台德酸催化剂并形成碳正离子中间体。
• Dual Intermolecular Allylic C-H Functionalization of the Tetrasubstituted Alkene Scaffold
  作者：Claudio Martínez、Kilian Muñiz

  DOI：10.1002/ejoc.201701624

  日期：2018.3.14

  Simple activation of chloramine‐T by a Brønsted acid generates N‐chlorotosylamide, which serves as a reagent for the selective double C–H functionalization at the allylic position of tetrasubstituted alkenes.

  布朗斯台德酸对氯胺-T的简单活化会生成N-氯代甲苯磺酰胺，可作为四取代烯烃的烯丙基位置处选择性双CH官能化的试剂。
• Olefin-Assisted Iron-Catalyzed Alkylation of Aryl Chlorides
  作者：Samet Gülak、Tim N. Gieshoff、Axel Jacobi von Wangelin

  DOI：10.1002/adsc.201300095

  日期：2013.8.12

  AbstractA selective and operationally simple iron‐catalyzed cross‐coupling of aryl chlorides with alkylmagnesium halides has been developed. The reaction tolerates various functional groups and exhibits high chemoselectivity even in the presence of aryl bromides. Mechanistic studies indicate the essential role of the olefin substituent for substrate activation. Competing polymerization and reduction are effectively suppressed.magnified image
• Reaktivit�t und Selektivit�t bei der Oxidation von Styrolderivaten. IV. Untersuchungen zur Oxidation von substituierten ?,?-Dimethylstyrolen
  作者：W. Y. Suprun

  DOI：10.1002/prac.19983400308

  日期：——

  The liquid phase oxidation of substituted (p-MeO-, p-Cl-, m-CF3-) 2-aryl-3-methyl-but-2-enes, of 1,1-diphenyl-2-methyl-propene, of 1-ethoxy-2-methyl-1-phenyl-propene and of 9-isopropylidene-fluorene with pure oxygen was investigated in chlorobenzene solution and in presence of cumene and of cumene hydroperoxide in the temperature range 65-125 degrees C. The product yields were determined gaschromatographically. The differences of the activation energies of epoxide formation and the parallel reactions were calculated. They amount to 19-48 kJ/mol. The epoxide selectivity increases with increasing temperature and increasing concentration of olefin. The relative chain propagation constants (k(pC=C)) were determined by competitive oxidation with cumene. The k(pC=C) values of substituted beta,beta-dimethylstyrenes can be correlated by a LFE-relationship with the ionisation energies of the olefins.