1-异丙基-4-(2-苯基乙烯基)苯 | 40231-48-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 1-异丙基-4-(2-苯基乙烯基)苯
• 英文名称: (E)-1-isopropyl-4-styrylbenzene
• 英文别名: 1-Isopropyl-4-(2-phenylvinyl)benzene；1-[(E)-2-phenylethenyl]-4-propan-2-ylbenzene
• CAS: 40231-48-9
• 化学式: C₁₇H₁₈
• 分子量: 222.33
• InChiKey: SYHLZZJWGVXLLZ-CMDGGOBGSA-N

物化性质

• 熔点：
  86-88 °C
• 沸点：
  329.8±17.0 °C(Predicted)
• 密度：
  0.998±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-isopropyl-4-(phenylethynyl)benzene 在 Lindlar's catalyst 氢气 、 碘 作用下， 以 乙醇 、 Petroleum ether 为溶剂， 生成 1-异丙基-4-(2-苯基乙烯基)苯
  参考文献：
  名称：

  Merkushev, E. B.; Skorokhodova, T. S., Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 308 - 311

  摘要：

  DOI：

文献信息

• Synthesis of 1,2-Diarylethylenes by Pd-Catalyzed One-Pot Reaction of Benzyl Halides, Tosylhydrazide, and Aryl Aldehydes
  作者：Xu Shen、Ping Liu、Yan Li、Bin Dai

  DOI：10.2174/1570178615666171222163927

  日期：2018.7.2

  Background: Substituted olefins are versatile functional groups and intermediates in chemistry, medicine, electronics, and optics and materials science fields because of their unique properties. One important class of substituted olefins 1,2-diarylethylenes have attracted considerable attention due to their presence in both natural products and pharmacologically active substances. Methods: In this paper, we developed a one-pot two-step coupling reaction of aryl aldehydes, tosylhydrazide with benzyl halides by using inexpensive Pd(PPh3)4 as catalyst, leading to a variety of 1,2- diphenylethenes derivatives with moderate to good yields. Results: The desired 1,2-diarylethylenes were obtained in 46-96% yields via Pd(0)-catalyzed one-pot reaction of benzyl halides, tosylhydrazide, and aryl aldehydes. Conclusion: The catalytic system presented here enables the use of easily accessible starting materials and good functional group tolerance.

  背景：取代烯烃由于其独特的性质，在化学、医药、电子学和光学以及材料科学领域中是一类多用途的功能团和中间体。其中，1,2-二芳基亚乙烯类取代烯烃因其存在于天然产物和具有药理活性的物质中而引起了相当大的关注。 方法：本文中，我们开发了一种以廉价的Pd(PPh3)4为催化剂，苯甲基卤代物与芳醛和甲苯磺酰肼的一锅法两步偶联反应，得到了中等至良好产率的多种1,2-二苯乙烯衍生物。 结果：通过Pd(0)催化的苯甲基卤代物、甲苯磺酰肼和芳醛的一锅法反应，得到了期望的1,2-二芳基亚乙烯，产率为46-96%。 结论：这里提出的催化体系使得易于获取的起始材料和良好的官能团耐受性得以应用。
• Zinc Metal-Promoted Stereoselective Olefination of Aldehydes and Ketones with<i>gem</i>-Dichloro Compounds in the Presence of Chlorotrimethylsilane
  作者：Yoshio Ishino、Masatoshi Mihara、Shintaro Nishihama、Ikuzou Nishiguchi

  DOI：10.1246/bcsj.71.2669

  日期：1998.11

  A combination of zinc metal and a catalytic amount of chlorotrimethylsilane has been found to promote the transformation of various aldehydes and ketones with gem-dichloro compounds, such as benzylidene dichloride (1a) and methyl dichloroacetate (1b), to the corresponding cross-coupling products, such as substituted styrene 3 and methyl acrylates 4 derivatives, under mild reaction conditions in THF. The E-isomer of the corresponding alkenes was obtained stereoselectively in good-to-excellent yields. The reaction serves as a very convenient one-pot procedure.

  将锌金属与催化量的氯三甲基硅烷结合，已被发现能够促进各种醛和酮与gem-二氯化合物的转化，如苄叉二氯化物（1a）和二氯乙酸甲酯（1b），生成相应的交叉偶联产物，如取代苯乙烯3和甲基丙烯酸酯4衍生物，反应在四氢呋喃的温和反应条件下进行。相应烯烃的E-异构体以良好至优良的产率选择性获得。该反应作为一种非常方便的一锅法程序。
• Suzuki and Heck coupling reactions mediated by palladium complexes bearing trans-spanning diphosphines
  作者：Rhett C. Smith、Christina R. Bodner、Meredith J. Earl、Nathaniel C. Sears、Nicholas E. Hill、Lee M. Bishop、Nicholas Sizemore、Dave T. Hehemann、Justin J. Bohn、John D. Protasiewicz

  DOI：10.1016/j.jorganchem.2004.09.077

  日期：2005.1

  Palladium complexes of three trans-spanning diphosphines are examined for effecting C–C coupling reactions. Ten aryl halides of varying electron density were screened in Suzuki coupling reactions with phenylboronic acid and in Heck reactions with styrene. The results are discussed in terms of the unique flexibility and shape of the meta-terphenyl backbone upon which the diphosphine ligand is built.

  考察了三种跨跨二膦的钯配合物对CC偶联反应的影响。在与苯硼酸的Suzuki偶联反应和与苯乙烯的Heck反应中，筛选了十个电子密度不同的芳基卤化物。根据在其上建立二膦配体的间-三联苯骨架的独特柔韧性和形状来讨论结果。
• Synthesis of (E)-Stilbenes and (E,E)-1,4-Diphenylbuta-1,3-diene Promoted by Boron Trifluoride-Diethyl Ether Complex
  作者：T. Narender、K. Papi Reddy、G. Madhur

  DOI：10.1055/s-0029-1217010

  日期：2009.11

  developed to regioselectively synthesize (E)-stilbenes and (E,E)-1,4-diphenylbuta-1,3-diene in good to excellent yields in the presence of boron trifluoride-diethyl ether complex as a catalyst in a short reaction (30-60 s) at room temperature. boron trifluoride-diethyl ether complex - (E)-stilbenes - (E,E)-1,4-diphenylbuta-1,3-diene - ketones - regioselectivity

  已经开发了一种有效，简单且实用的方法，可以在三氟化硼-二乙基硼的存在下，以良好至极佳的收率选择性地合成（E）-苯乙烯和（E，E）-1,4-二苯基丁a -1,3-二烯。室温下短时间反应（30-60 s）中作为醚配合物的催化剂。 三氟化硼-乙醚复合物-（E）-对苯二酚-（E，E）-1,4-二苯基丁a -1,3-二烯-酮-区域选择性
• A New Route to <i>E</i> ‐Stilbenes through the Transition‐Metal‐Free KO <i>t</i> Bu/DMF‐Promoted Direct Coupling of Alcohols with Phenyl Acetonitriles
  作者：Xiaoping Liu、Jean‐Marc Sotiropoulos、Marc Taillefer

  DOI：10.1002/ejoc.202200631

  日期：2022.7.14

  A new route to E-Stilbenes, based on the transition metal free, KOtBu/DMF promoted activation and direct coupling of alcohols with phenyl acetonitriles, is reported. A variation allowing the selective synthesis of N-Heteroarenes and a mechanism proceeding via the activation of alcohols under alkyl formate intermediates are also reported.

  报道了一种基于不含过渡金属、KO t Bu/DMF 的E-二苯乙烯的新途径，它促进了醇与苯基乙腈的活化和直接偶联。还报道了一种允许选择性合成 N-杂芳烃的变化以及通过在甲酸烷基酯中间体下活化醇进行的机制。