trans-2-(o-methyl-β-styryl)naphthalene | 80663-25-8

• 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: trans-2-(o-methyl-β-styryl)naphthalene
• 英文别名: (E)-2-(2-O-tolylvinyl)naphthalene；(E)-2-(2-methylstyryl)naphthalene；2-[(E)-2-(2-methylphenyl)ethenyl]naphthalene
• CAS: 80663-25-8
• 化学式: C₁₉H₁₆
• 分子量: 244.336
• InChiKey: WRVCAPJYMVVOSI-ZRDIBKRKSA-N

物化性质

• 熔点：
  90 °C(Solv: ethanol (64-17-5))
• 沸点：
  397.6±17.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  trans-2-(o-methyl-β-styryl)naphthalene 以5%的产率得到
  参考文献：
  名称：

  LAPOUVADE, R.;VEYRES, A.;HANAFI, NAIMA;COUTURE, A.;LABLACHE-COMBIER, A., J. ORG. CHEM., 1982, 47, N 7, 1361-1364

  摘要：

  DOI：
• 作为产物：
  描述：

  2-萘甲醇 在 4-二甲氨基吡啶 、 bis(1,5-cyclooctadiene)nickel (0) 、 1,3-双(二苯基膦)丙烷 、 potassium tert-butylate 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 0.25h， 生成 trans-2-(o-methyl-β-styryl)naphthalene
  参考文献：
  名称：

  Nickel-catalyzed synthesis of (E)-olefins from benzylic alcohol derivatives and arylacetonitriles via C–O activation

  摘要：

  描述了一种高效的镍催化合成方法，使用易得的苄基醇衍生物和芳基乙腈合成(E)-烯烃。这种转化应该通过涉及镍催化的交叉偶联，通过C-O活化和随后的立体选择性E2消除的串联过程进行。

  DOI：

  10.1039/c5cc10005d

文献信息

• Low-valent Niobium-mediated Synthesis of Indenes: Intramolecular Coupling Reaction of CF₃Group with Alkene C–H Bond
  作者：Kohei Fuchibe、Ken Mitomi、Takahiko Akiyama

  DOI：10.1246/cl.2007.24

  日期：2007.1

  CF3 group of o-alkenyl-α,α,α-trifluorotoluenes underwent intramolecular coupling reaction with the alkene C–H bond under NbCl5/LiAlH4 system. Substituted indenes were obtained in good yields.

  CF3取代的o-烯烃-α,α,α-三氟甲苯在NbCl5/LiAlH4体系下与烯烃C–H键发生了分子内偶联反应。获得了产率良好的取代茚类化合物。
• d-Glucosamine as a Green Ligand for Palladium-Catalyzed Cross-Coupling of Aryl and Heteroaryl Halides
  作者：Nidhi Jain、Abadh Jha、Rahul Shahni

  DOI：10.1055/s-0034-1379612

  日期：——

  Naturally occurring d -glucosamine works as an efficient green alternative to phosphines in palladium-catalyzed Heck coupling of aryl and heteroaryl halides. An array of trans -stilbene derivatives, aryl naphthyl alkenes, heteroaryl olefins, and β-aryl-substituted acrylates has been synthesized in short reaction times in moderate to high yields.

  在钯催化的芳基和杂芳基卤化物的 Heck 偶联中，天然存在的 d-葡糖胺可作为膦的有效绿色替代品。一系列反式二苯乙烯衍生物、芳基萘基烯烃、杂芳基烯烃和 β-芳基取代的丙烯酸酯已在较短的反应时间内以中等至高产率合成。
• Photocyclization of 1,2-diarylethylenes in primary amines. A convenient method for the synthesis of dihydro aromatic compounds and a means of reducing the loss of methyl groups during the cyclization of o-methylstilbenes
  作者：Rene Lapouyade、Alain Veyres、Naima Hanafi、Axel Couture、Alain Lablache-Combier

  DOI：10.1021/jo00346a045

  日期：1982.3
• Mechanism of Photoisomerization of 1-Naphthyl-2-Phenylethylenes in Organic Glasses
  作者：Lan-Ying Yang、Robert S. H. Liu

  DOI：10.1111/j.1751-1097.2007.00183.x

  日期：2007.11

  AbstractPhotoisomerization reactions of cis isomers of 1‐β‐naphthyl‐2‐phenylethylene, an o‐methylated homolog and 1‐α‐naphthyl‐2‐phenylethylene in organic glasses at liquid nitrogen temperature were studied. Reactions were followed by changes in UV‐absorption spectra of the irradiated samples. Formation of an unstable trans‐photoproduct was detected only with the o‐methylated homolog. The results are consistent with high regioselective Hula‐twist photoisomerization at the benzylic sites of the three compounds examined. Calculated data on relative energies of the conformers of both the cis and the trans isomers are in agreement with the suspected conformational population of the starting materials and the photoproducts.
• NAGEL D. L.; KUPPER R.; ANTONSON K.; WALLCAVE L., J. ORG. CHEM., 1977, 42, NO 22, 3626-3628
  作者：NAGEL D. L.、 KUPPER R.、 ANTONSON K.、 WALLCAVE L.

  DOI：——

  日期：——