2-(4-methoxystyryl)naphthalene | 845624-64-8

• 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: 2-(4-methoxystyryl)naphthalene
• 英文别名: (Z)-2-(4-methoxystyryl)naphthalene；2-[(Z)-2-(4-methoxyphenyl)ethenyl]naphthalene
• CAS: 845624-64-8
• 化学式: C₁₉H₁₆O
• 分子量: 260.335
• InChiKey: AKKNWIXYHZJSBW-SREVYHEPSA-N

物化性质

• 沸点：
  434.8±20.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-(3-Bromoprop-1-ynyl)-2-ethenylbenzene 在 potassium tert-butylate 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 2-(4-methoxystyryl)naphthalene
  参考文献：
  名称：

  炔丙基-烯基异构化和电环化用于for盐的功能：多取代乙烯基苯和萘的一锅法合成

  摘要：

  AbstractPhosphonium salts are widely used in organic synthesis as the precursor of Wittig reagents but highly functionalized phosphonium salts are not readily available. We have developed a sequence of propargyl–allenyl isomerizations and electrocyclizations for the functionalization of phosphonium salts via simple starting materials, which may provide an efficient one‐pot synthesis of polysubstituted vinylbenzenes and naphthalenes.magnified image

  DOI：

  10.1002/adsc.201300573

文献信息

• Stereospecific Iron-Catalyzed Carbon (sp²)–Carbon (sp²) Cross-Coupling of Aryllithium with Vinyl Halides
  作者：Peng Chen、Zhi-Yong Wang、Xiao-Shui Peng、Henry N.C. Wong

  DOI：10.1021/acs.orglett.1c01318

  日期：2021.6.4

  We present herein an efficient synthetic protocol involving iron-catalyzed cross-coupling of organolithium compounds with vinyl halides as key coupling partners. More than 30 examples were obtained with moderate to good yields and high stereoselectivities. The practicality of this method is evidenced by a gram-scale synthesis. In addition, a preliminary mechanistic investigation was also performed

  我们在此提出了一种有效的合成方案，涉及有机锂化合物与乙烯基卤化物作为关键偶联伙伴的铁催化交叉偶联。获得了 30 多个具有中等至良好产率和高立体选择性的实例。克级合成证明了该方法的实用性。此外，还进行了初步的机械调查。
• Further Naphthylcombretastatins. An Investigation on the Role of the Naphthalene Moiety
  作者：Ana B. S. Maya、Concepción Pérez-Melero、Carmen Mateo、Dulce Alonso、José Luis Fernández、Consuelo Gajate、Faustino Mollinedo、Rafael Peláez、Esther Caballero、Manuel Medarde

  DOI：10.1021/jm0310737

  日期：2005.1.1

  By synthesis and biological studies of new naphthalene analogues of combretastatins, we have found that the naphthalene is a good surrogate for the isovanillin moiety (3-hydroxy-4methoxyphenyl) of combretastatin A-4, always generating highly cytotoxic analogues when combined with the 3,4,5-trimethoxyphenyl or related systems. On the other hand, when the naphthalene replaces the 3,4,5-trimethoxyphenyl moiety, the cytotoxic activity is largely decreased. The most cytotoxic naphthalene analogues of combretastatins, which also produce inhibition of tubulin polymerization, exerted their antimitotic effects through microtubule network disruption and subsequent G(2)/M arrest of the cell cycle in human cancer cells.