(E)-2-styryl-1,1'-biphenyl | 34662-94-7

• 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)-2-styryl-1,1'-biphenyl
• 英文别名: a-Phenyl-stilben；1-phenyl-2-[(E)-2-phenylethenyl]benzene
• CAS: 34662-94-7
• 化学式: C₂₀H₁₆
• 分子量: 256.347
• InChiKey: CBJPRTGKMYOVJO-FOCLMDBBSA-N

物化性质

• 熔点：
  61-63 °C
• 沸点：
  417.1±25.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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)-2-styryl-1,1'-biphenyl 在 potassium tert-butylate 、 溴 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 8.0h， 生成 2-(苯基乙炔基)-1,1'-联苯
  参考文献：
  名称：

  The First Aryne Evolution from the Reactions of Selenonium Salts with Aryllithiums

  摘要：

  The first example of the benzyne generation was found in the reactions of alkynylselenonium salt 1a with 1.0 equiv. of phenyllithium in THF at room temperature for 3 h. The formation of the aryne intermediate was confirmed in the reactions of alkynylselenonium salt 1b and tri-p-tolylselenonium salt 6b with tolyllithium, which gave a mixture of alkynylbiphenyl derivatives 18 and 19 in 19% yield (18:19=11:8) and a mixture of bitolyls 28 and 29 in 63% yield (28:29=2:1), respectively. The reaction mechanisms of these reactions are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01090-x
• 作为产物：
  描述：

  biphenyl-2-yl-lithium 在 phosphorus pentoxide 作用下， 生成 (E)-2-styryl-1,1'-biphenyl
  参考文献：
  名称：

  Photocyclization of 2-vinylbiphenyls and related compounds under triplet sensitization: an adiabatic reaction on the triplet surface

  摘要：

  DOI：

  10.1021/ja00309a030

文献信息

• Palladium-Catalyzed Mizoroki–Heck Reaction of Nitroarenes and Styrene Derivatives
  作者：Toshimasa Okita、Kitty K. Asahara、Kei Muto、Junichiro Yamaguchi

  DOI：10.1021/acs.orglett.0c00983

  日期：2020.4.17

  We have developed a Mizoroki–Heck reaction of nitroarenes with alkenes under palladium catalysis. The use of a Pd/BrettPhos catalyst promoted the alkenylation, whereas other catalysts led to a decrease in the product yield. In addition to nitroarenes, nitroheteroarenes were also applicable to the present reaction. The combination of a nucleophilic aromatic substitution (SNAr) with the denitrative alkenylation

  我们已经开发了钯催化下硝基芳烃与烯烃的Mizoroki-Heck反应。Pd / BrettPhos催化剂的使用促进了烯基化，而其他催化剂导致产物收率下降。除硝基芳烃外，硝基杂芳烃也适用于本反应。亲核芳族取代（S的组合Ñ AR）与denitrative烯基化产生在单罐操作的多官能化的芳烃。
• <i>N</i>,<i>N-</i>Diethyl <i>O-</i>Carbamate: Directed Metalation Group and Orthogonal Suzuki−Miyaura Cross-Coupling Partner
  作者：Aurora Antoft-Finch、Tom Blackburn、Victor Snieckus

  DOI：10.1021/ja907700e

  日期：2009.12.16

  was established to be a crucial parameter for this transformation. When combined with DoM and traditional Pd-catalyzed Suzuki-Miyaura strategies, the methodology offers concise routes to uniquely substituted molecules, avoiding the need for protection/deprotection of the phenol and the use of strongly nucleophilic cross-coupling partners.

  首次 Suzuki-Miyaura 交叉偶联芳基 O-氨基甲酸酯是定向邻位金属化 (DoM) 化学中的一种多功能且强大的定向金属化基团 (DMG)，使用廉价、长期稳定的催化剂 NiCl(2)(PCy) 进行描述(3))(2)。芳基和杂芳基 O-氨基甲酸酯具有广泛的合成范围和良好的效率。水和游离硼酸和环硼氧烷之间的水解平衡的作用被确定为这一转化的关键参数。当与 DoM 和传统 Pd 催化的 Suzuki-Miyaura 策略相结合时，该方法为独特的取代分子提供了简洁的途径，避免了对苯酚的保护/脱保护和使用强亲核交叉偶联伙伴的需要。
• Oxidative, Iodoarene‐Catalyzed Intramolecular Alkene Arylation for the Synthesis of Polycyclic Aromatic Hydrocarbons
  作者：Zhensheng Zhao、Liam H. Britt、Graham K. Murphy

  DOI：10.1002/chem.201804786

  日期：2018.11.16

  metal‐free and chemoselective oxidative intramolecular coupling of arene and alkene C−H bonds is reported. The active hypervalent iodine (HVI) reagent, generated catalytically in situ from iodotoluene and meta‐chloroperoxybenzoic acid (m‐CPBA), reacts with o‐vinylbiphenyls to generate polyaromatic hydrocarbons in up to 95 % yield. Experimental evidence suggests the reactions proceed though vinyliodonium

  据报道，芳烃和烯烃CH键具有催化，无金属和化学选择性的氧化分子内偶联作用。由碘代甲苯和间氯过氧苯甲酸（m- CPBA）原位催化生成的活性高价碘（HVI）试剂与邻乙烯基联苯反应生成多芳烃，产率高达95％。实验证据表明，反应是通过乙烯基碘鎓和（可能的）亚乙烯基phen中间体进行的。
• 2,3-Dichloro-5,6-dicyano-<i>para</i>-benzoquinone (DDQ)/Methanesulfonic Acid (MsOH)-Mediated Intramolecular Arene-Alkene Oxidative Coupling
  作者：Ko Hoon Kim、Cheol Hee Lim、Jin Woo Lim、Jae Nyoung Kim

  DOI：10.1002/adsc.201301169

  日期：2014.3.10

  An efficient intramolecular arene‐alkene oxidative coupling of 1,4‐diaryl‐1,3‐butadienes has been developed involving the use of a 2,3‐dichloro‐5,6‐dicyano‐para‐benzoquinone (DDQ)/acid catalyst. The reaction involves the generation of a radical cation by abstraction of an electron from the substrate with DDQ, an intramolecular Friedel–Crafts‐type reaction, and the loss of hydrogen radical.

  已经开发出一种有效的1,4-二芳基-1,3-丁二烯分子内芳烃-烯烃氧化偶联方法，其中涉及使用2,3-二氯-5,6-二氰基对对苯二酚（DDQ）/酸催化剂。该反应涉及通过用DDQ从底物中提取电子来产生自由基阳离子，分子内Friedel-Crafts型反应以及氢自由基的损失。
• 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。