(E)-1-methyl-3-(4-methylstyryl)benzene | 37163-81-8

• 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: (E)-1-methyl-3-(4-methylstyryl)benzene
• 英文别名: trans-3,4'-dimethylstilbene；E-3,4'-dimethylstilbene；1-methyl-3-[(E)-2-(4-methylphenyl)ethenyl]benzene
• CAS: 37163-81-8
• 化学式: C₁₆H₁₆
• 分子量: 208.303
• InChiKey: VHHIBWHCXFSZKM-ZHACJKMWSA-N

物化性质

• 熔点：
  97-98 °C
• 沸点：
  323.9±22.0 °C(Predicted)
• 密度：
  1.015±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  (E)-1-methyl-3-(4-methylstyryl)benzene 在 溴 、 sodium bromide 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Electrophilic bromination of aromatic conjugated olefins. II. Mechanism of the dual-path additions in stilbene bromination. Evidence from multiple substituent effects for carbonium ion intermediates

  摘要：

  DOI：

  10.1021/jo00943a019
• 作为产物：
  描述：

  3-甲基苄基氯 在 lithium 、 对甲苯磺酸 作用下， 以 乙醚 、 苯 为溶剂， 反应 4.5h， 生成 (E)-1-methyl-3-(4-methylstyryl)benzene
  参考文献：
  名称：

  Burkow, Ivan C.; Sydnes, Leiv K.; Ubeda, Danielle C. N., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1987, vol. 41, # 4, p. 235 - 244

  摘要：

  DOI：

文献信息

• 1,2,3-Triazol-5-ylidene–palladium complex catalyzed Mizoroki–Heck and Sonogashira coupling reactions
  作者：Sayuri Inomata、Hidekatsu Hiroki、Takahiro Terashima、Kenichi Ogata、Shin-ichi Fukuzawa

  DOI：10.1016/j.tet.2011.07.045

  日期：2011.9

  The bis-1,4-dimesityl-1,2,3-triazol-5-ylidene–palladium complex (1a) successfully catalyzes the Mizoroki–Heck and Sonogashira coupling reactions with aryl bromides to give the corresponding alkenes and alkynes, respectively, in good to excellent yields. In the Mizoroki–Heck reaction, electron-rich, electron-poor, and functionalized aryl bromides and alkenes are tolerated, while the substrates are limited

  bis-1,4-dimesityl-1,2,3-triazol-5- ylidene-钯络合物（1a）成功催化了Mizoroki-Heck和Sonogashira与芳基溴的偶联反应，分别得到相应的烯烃和炔烃好到极好的产量。在Mizoroki-Heck反应中，可以耐受富电子，贫电子和官能化的芳基溴化物和烯烃，而在Sonogashira偶联反应中，底物仅限于贫电子的芳基卤化物。在特定条件下，钯配合物还催化与芳基氯的交叉偶联反应，从而获得比bis-IMes-Pd配合物类似物更高的产品收率（2）。
• Transition metal-free domino sequential synthesis of (E)-stilbenes, biaryl methanes and biaryl ethers using Et2AlCl as a Lewis acid
  作者：Satinath Sarkar、Manoranjan Jana、Narender Tadigoppula

  DOI：10.1039/c3ra42955e

  日期：——

  A transition metal-free domino process has been developed, for the first time, to synthesize (E)-stilbenes, biaryl methanes and biaryl ethers from substituted α,β-unsaturated ketones, benzyl acetones and phenacyl ethers, respectively, in moderate to good yields at room temperature using diethyl aluminium chloride (Et2AlCl) as a Lewis acid.

  首次开发了无过渡金属的多米诺法，以中等至良好的程​​度分别由取代的α，β-不饱和酮，苄基丙酮和苯甲醚合成（E）-对苯二甲酸酯，联芳基甲烷和联芳基醚。在室温下使用二乙基氯化铝（Et 2 AlCl）作为路易斯酸。
• Efficient Mizoroki–Heck coupling reactions using phosphine-modified Pd(II)–picolinate complex
  作者：Sonam Sharma、Bibhas R. Sarkar

  DOI：10.1080/00397911.2018.1428347

  日期：2018.4.18

  ABSTRACT Efficient Mizoroki–Heck couplings were obtained using a very easily synthesizable palladium(II) complex of hemilabile N–O ligand (picolinate), with high turnover frequencies up to >10,000 h−1, in just 15 min, with high selectivity of >99% to the desired products. Wide applicability of the simple-looking palladium complex catalyst was established with differently functionalized substrates.

  摘要 高效的 Mizoroki-Heck 偶联是使用一种非常容易合成的半稳定 N-O 配体（吡啶甲酸）的钯 (II) 复合物获得的，具有高达 >10,000 h-1 的高周转频率，仅需 15 分钟，具有 > 99% 达到所需产品。外观简单的钯配合物催化剂的广泛适用性是通过不同功能化的底物建立的。催化剂筛选研究揭示了催化剂性能对不同反应参数和条件的依赖性的复杂细节，并得出了优化的简便方法。图形概要
• Acceptorless dehydrogenative construction of CN and CC bonds through catalytic aza-Wittig and Wittig reactions in the presence of an air-stable ruthenium pincer complex
  作者：Nandita Biswas、Kalicharan Das、Bitan Sardar、Dipankar Srimani

  DOI：10.1039/c8dt04725a

  日期：——

  aza-Wittig type reaction. The reaction is catalyzed by an acridine-derived ruthenium pincer complex and does not use any oxidant. The present protocol offers a wide substrate scope, including aliphatic, aryl or heteroaryl alcohol/azides. This expeditious protocol was successfully applied to construct a CC bond directly from alcohol via dehydrogenative Wittig reaction. Furthermore, the synthesis of structurally

  C N键的构建是通过aza-Wittig型反应将醇与叠氮化物进行脱氢偶联而实现的。该反应由an啶衍生的钌钳配合物催化，并且不使用任何氧化剂。本协议提供了广泛的底物范围，包括脂族，芳基或杂芳基醇/叠氮化物。该快速方案已成功应用于通过脱氢Wittig反应直接从醇中构建C C键。此外，通过该方法还可以合成结构上重要的吡咯并[1,4]苯并二氮杂衍生物。
• Characterization of cation radical reactions. Aminium salt-catalysed Diels–Alder reactions
  作者：Wang Yueh、Nathan L. Bauld

  DOI：10.1039/p29960001761

  日期：——

  Kinetic studies of the Diels–Alder cycloadditions of a series of trans-stilbenes (2) to 2,3-dimethylbuta-1,3-diene (3), catalysed by tris(4-bromophenyl)aminium hexachloroantimonate (1˙+), reveal a curved Hammett–Brown plot, consistent with a mechanistic transition from reversible to rate determining ionization of 2 to 2˙+ as the substituents become progressively more electron donating. Further, substituent

  Kinetic studies of the Diels–Alder cycloadditions of a series of trans-stilbenes (2) to 2,3-dimethylbuta-1,3-diene (3), catalysed by tris(4-bromophenyl)aminium hexachloroantimonate (1˙+), reveal a curved Hammett–Brown plot, consistent with a mechanistic transition from reversible to rate determining ionization of 2 to 2˙+ as the substituents become progressively more electron donating. Further, substituent