(Z)-1-methyl-4-(2-phenylprop-1-enyl)benzene | 113312-81-5

• 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: (Z)-1-methyl-4-(2-phenylprop-1-enyl)benzene
• 英文别名: 1-methyl-4-(2-phenylprop-1-en-1-yl)benzene；2-phenyl-1-p-tolyl-1-propene；(Z)-1-(4-methylphenyl)-2-phenylprop-1-ene；1-methyl-4-[(Z)-2-phenylprop-1-enyl]benzene
• CAS: 113312-81-5
• 化学式: C₁₆H₁₆
• 分子量: 208.303
• InChiKey: YLLURBLBZOUAPN-OWBHPGMISA-N

物化性质

• 熔点：
  55-56 °C
• 沸点：
  302.5±17.0 °C(Predicted)
• 密度：
  0.997±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 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

• 作为产物：
  描述：

  1-(1-phenylethyl)-1H-benzo[d][1,2,3]triazole 在 正丁基锂 、 四氯化钛 、 铜 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 1.0h， 生成 (Z)-1-methyl-4-(2-phenylprop-1-enyl)benzene
  参考文献：
  名称：

  Trans-Selective Olefination of Carbonyl Compounds by Low-Valent Titanium-Mediated Dehydroxybenzotriazolylation

  摘要：

  Lithiation with n-butyllithium of a variety of benzotriazole derivatives 1a-f and 5a-d, all containing a proton alpha to the benzotriazolyl moiety, gave anions which underwent addition to aliphatic, aromatic, and alpha,beta-unsaturated aldehydes and cyclic and acyclic ketones. The resultant N-(beta-hydroxyalkyl)benzotriazole derivatives 3a-m, 6a-g, 9a-d, and 10a were dehydroxybenzotriazolylated when treated with low-valent titanium to give alkenes 4a-m, dienes 7a-j, and triene 11a, with selectivity for the trans isomers without separation of diastereoisomeric intermediates. This method offers an alternative to the three most frequently used methods for the formation of alkenes from carbonyl compounds-the Wittig, Peterson, and Julia reactions-especially in the formation of tri- and tetrasubstituted alkenes.

  DOI：

  10.1021/jo980616v

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。
• Nickel-Catalyzed Alkenylative Cross-Coupling Reaction of Alkyl Sulfides
  作者：Kentaro Ishizuka、Hirofumi Seike、Takuji Hatakeyama、Masaharu Nakamura

  DOI：10.1021/ja104155f

  日期：2010.9.29

  A novel cross-coupling reaction of alkyl aryl sulfides with aryl Grignard reagents has been achieved to produce the alkenyl-aryl coupling products in high yields by using catalytic Ni(cod)(2) and a bulky N-heterocyclic carbene ligand, SIPr.

  通过使用催化 Ni(cod)(2) 和庞大的 N-杂环卡宾配体 SIPr，实现了烷基芳基硫化物与芳基格氏试剂的新型交叉偶联反应，以高产率生产烯基-芳基偶联产物。
• Synthesis of new adamantyl-imine palladium(II) complexes and their application in Mizoroki-Heck and Suzuki-Miyaura C C cross-coupling reactions
  作者：Asanda C. Matsheku、Munaka C. Maumela、Banothile C.E. Makhubela

  DOI：10.1016/j.poly.2021.115280

  日期：2021.9

  electron-rich ligands for application in palladium-catalysed cross-coupling reactions. Accordingly, we have prepared some Schiff-base adamantyl ligands (L1-L3) and complexed them with [PdCl2(MeCN)2] to afford the (pre)catalysts C1-C3, which were successfully applied in Mizoroki-Heck and Suzuki-Miyaura carbon–carbon cross-coupling reactions. The cross-coupling reaction products were obtained in good

  改进碳-碳交叉偶联反应是一个持续的过程，寻找最通用和最稳定的催化剂前体引起了人们极大的兴趣。配体设计已被证明很重要，因为它负责提供金属中心周围的电子密度和空间饱和度，从而有助于立体电子特性。金刚烷基部分已被用于生成体积大且富含电子的配体，用于钯催化的交叉偶联反应。因此，我们制备了一些席夫碱金刚烷基配体 ( L1-L3 ) 并将它们与 [PdCl 2 (MeCN) 2 ]复合以提供（预）催化剂C1-C3，已成功应用于 Mizoroki-Heck 和 Suzuki-Miyaura 碳-碳交叉偶联反应。使用 0.5 mol% Pd 催化剂负载以良好的产率获得交叉偶联反应产物。C2和C3在 Mizoroki-Heck 偶联反应中表现出显着的活性，该反应涉及底物在烯烃和芳基卤化物（包括 4-Cl、4-CH 3、-CO 2 Me 和 -CO 2等）。我们还观察到 Suzuki-Miyaura 交叉偶联
• Iron-catalysed tandem cross-dehydrogenative coupling (CDC) of terminal allylic C(sp3) to C(sp2) of styrene and benzoannulation in the synthesis of polysubstituted naphthalenes
  作者：Hua Liu、Li Cao、Jia Sun、John S. Fossey、Wei-Ping Deng

  DOI：10.1039/c2cc17330a

  日期：——

  A novel iron-catalysed tandem cross-dehydrogenative coupling and benzoannulation process was developed for the synthesis of biologically and synthetically important polysubstituted naphthalene derivatives from simple 1,2-aryl-propenes and styrenes in moderate to good yields.

  本研究开发了一种新型铁催化串联交叉脱氢偶联和苯并氮化工艺，用于从简单的 1,2-芳基丙烯和苯乙烯合成具有重要生物和合成意义的多取代萘衍生物，产率为中等到良好。
• Phosphapalladacycle-Catalyzed Heck Reactions for Efficient Synthesis of Trisubstituted Olefins: Evidence for Palladium(0) Intermediates
  作者：Matthias Beller、Thomas H. Riermeier

  DOI：10.1002/(sici)1099-0682(199801)1998:1<29::aid-ejic29>3.0.co;2-x

  日期：1998.1

  The coupling reaction of 1,1-disubstituted olefins (α-methylstyrene, n-butyl methacrylate) with various aryl bromides (Heck reaction) has been studied as a new concept to synthesize trisubstituted olefins. Surprisingly, the nature of the base dramatically influences the product distribution. Thus, a systematic investigation on the role of base in Heck reactions of 1,1-disubstituted olefins was performed

  1,1-二取代烯烃（α-甲基苯乙烯、甲基丙烯酸正丁酯）与各种芳基溴化物的偶联反应（Heck 反应）已作为合成三取代烯烃的新概念进行了研究。令人惊讶的是，碱的性质极大地影响了产品分布。因此，对碱在 1,1-二取代烯烃的 Heck 反应中的作用进行了系统研究。较少配位的碱如 NaOAc、NaOBz 或 Na2CO3 产生区域异构体的统计分布，其中末端烯烃 10 作为主要产物。然而，通过使用胺类如 Bu3N 或二异丙基乙胺 (DIPEA) 作为基础内烯烃，可以高选择性地合成。以磷钯环 3 作为催化剂前体，我们能够获得高达 1000 的催化剂周转数，而 Pd(OAc)2/2PPh3 的活性低一个数量级。通过动力学研究对反应曲线的分析导致了催化剂前体 3 的还原和随后氧化加成以形成 12 作为催化活性中间体的假设。