2-[2-(4-methylphenyl)-(Z)-ethenyl]-naphthalene | 35160-96-4

• 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-[2-(4-methylphenyl)-(Z)-ethenyl]-naphthalene
• 英文别名: cis-1-(2-Naphthyl)-2-(p-tolyl)ethylen；2-[(Z)-2-(4-methylphenyl)ethenyl]naphthalene
• CAS: 35160-96-4
• 化学式: C₁₉H₁₆
• 分子量: 244.336
• InChiKey: CXELECXZLMQZEW-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 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：

  2-[2-(4-methylphenyl)-(Z)-ethenyl]-naphthalene 在 碘 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 2-[(E)-2-(4-甲基苯基)乙烯基]萘
  参考文献：
  名称：

  对官能化的[5]-和[6]碳杂戊烯的光化学合成的研究

  摘要：

  据报道，通过不对称双-对-苯乙烯类化合物的氧化光环化反应，可获得不对称螺旋薄荷基酯的有效途径。发达的路线允许在环A，E或F上引入官能团，并且已经研究了取代基图案对光化学反应的影响。当使用以70:30的异构体比率合成的二薄荷基螺旋烯酯进行双重手性诱导策略时，观察到非对映选择性。

  DOI：

  10.1021/jo900785k
• 作为产物：
  描述：

  (4-甲基苯基)甲醇 在 正丁基锂 、 三溴化磷 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 苯 为溶剂， 反应 0.5h， 生成 2-[2-(4-methylphenyl)-(Z)-ethenyl]-naphthalene
  参考文献：
  名称：

  Further Naphthylcombretastatins. An Investigation on the Role of the Naphthalene Moiety

  摘要：

  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.

  DOI：

  10.1021/jm0310737

文献信息

• Olefination with Sulfonyl Halides and Esters: <i>E</i> -Selective Synthesis of Alkenes from Semistabilized Carbanion Precursors
  作者：Bartosz Górski、Dariusz Basiak、Alicja Talko、Tymoteusz Basak、Tomasz Mazurek、Michał Barbasiewicz

  DOI：10.1002/ejoc.201701766

  日期：2018.4.23

  Sulfur‐based olefination with Horner–Wadsworth–Emmons‐type mechanism is systematically studied. Nonstabilized and semistabilized carbanion precursors react with carbonyl compounds giving good yields of olefins, and for the latter reagents E isomers of alkenes predominate.

  系统地研究了基于霍纳-沃兹沃思-埃蒙斯型机理的硫基烯烃化反应。未稳定的和半稳定的碳负离子前体与羰基化合物反应，可提供良好的烯烃收率，而对于后一种试剂，烯烃的E异构体占主导地位。
• Hexahelicene. Absolute configuration
  作者：David A. Lightner、Daniel T. Hefelfinger、Thomas W. Powers、Gerard W. Frank、Kenneth N. Trueblood

  DOI：10.1021/ja00765a041

  日期：1972.5
• 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.
• Studies toward the Photochemical Synthesis of Functionalized [5]- and [6]Carbohelicenes
  作者：Morwenna S. M. Pearson、David R. Carbery

  DOI：10.1021/jo900785k

  日期：2009.8.7

  An efficient route to nonsymmetrical helical menthyl esters by means of an oxidative photocyclization reaction of dissymmetric bis-stilbenes is reported. The developed route allows the introduction of functionality on rings A, E, or F, and the influence of the substituent pattern on the photochemical reaction has been examined. Diastereoselectivity is observed when a double chiral induction strategy

  据报道，通过不对称双-对-苯乙烯类化合物的氧化光环化反应，可获得不对称螺旋薄荷基酯的有效途径。发达的路线允许在环A，E或F上引入官能团，并且已经研究了取代基图案对光化学反应的影响。当使用以70:30的异构体比率合成的二薄荷基螺旋烯酯进行双重手性诱导策略时，观察到非对映选择性。