5-methoxy-2-phenylstyrene | 269391-98-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-methoxy-2-phenylstyrene
• 英文别名: 2-ethenyl-4-methoxy-1-phenylbenzene
• CAS: 269391-98-2
• 化学式: C₁₅H₁₄O
• 分子量: 210.276
• InChiKey: FBMZHOHMRRJVKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-methoxy-2-phenylstyrene 在 sodium azide 、 tetrabutylammonium tetrafluoroborate 、 一氯化碘 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 5.58h， 生成 8-methoxy-6-(tosylmethyl)phenanthridine
  参考文献：
  名称：

  乙烯基叠氮化物的无金属电化学偶联：菲啶和β-酮砜的合成

  摘要：

  据报道，分别通过联芳基乙烯基叠氮化物与叠氮化钠和苯磺酰肼的电化学氧化环偶联，可有效地和环保地合成菲啶。该反应在室温下在无分隔的池中进行，无需额外的金属催化或外源氧化剂。

  DOI：

  10.1002/ejoc.202001059
• 作为产物：
  描述：

  3-甲氧基苯乙酮 在 sodium tetrahydroborate 、 碘 、 silver trifluoroacetate 、 三苯基膦 、 nickel dichloride 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 xylene 为溶剂， 反应 15.0h， 生成 5-methoxy-2-phenylstyrene
  参考文献：
  名称：

  摘要：

  9,10-Dihydrophenanthrenes and phenanthrenes, mimics of natural compounds with strong antialgal activity, have been synthesized through cross-coupling of 1-(2-iodo-5-methoxy)-phenylethanol with variously substituted iodobenzenes. The synthetic compounds, bearing a hydroxyl or a methoxyl group at C-2 and a methyl in the C ring, were tested against the green alga Selenastrum capricornutum. All compounds, except 2-methoxy-7-methylphenanthrene, caused inhibition of algal growth by more than 70% at 10(-4) M, and many of them retained this strong activity at 10(-5) M.

  DOI：

  10.1023/a:1005463802388

文献信息

• 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。
• Vicinal Dichlorination of o-Vinylbiphenyls and the Synthesis of 9-(Arylmethyl)fluorenes via Tandem Friedel–Crafts Alkylations
  作者：Zhensheng Zhao、Islam Jameel、Graham K. Murphy

  DOI：10.1055/s-0037-1611562

  日期：2019.7

  room temperature. Treating the vic-dichlorides with 50 mol% AlCl3 in the presence of arene nucleophiles results in sequential intramolecular and intermolecular Friedel–Crafts alkylations to generate 9-(arylmethyl)fluorene derivatives. The dichlorination and alkylation reactions are operationally simple and tolerant of a variety of functional groups and substitution patterns, and give the products in

  抽象的 使邻乙烯基联苯与（二氯碘代）苯（PhICl 2）反应，可以迅速并在室温下以优异的收率得到邻二氯化物。在芳烃亲核试剂存在下用50 mol％AlCl 3处理vic- dichloride会导致分子内和分子间Friedel-Crafts烷基化顺序生成9-（芳基甲基）芴衍生物。二氯化和烷基化反应操作简单，可耐受多种官能团和取代方式，并能以中等至极好的收率得到产物。 使邻乙烯基联苯与（二氯碘代）苯（PhICl 2）反应，可以迅速并在室温下以优异的收率得到邻二氯化物。在芳烃亲核试剂存在下用50 mol％AlCl 3处理vic- dichloride会导致分子内和分子间Friedel-Crafts烷基化顺序生成9-（芳基甲基）芴衍生物。二氯化和烷基化反应操作简单，可耐受多种官能团和取代方式，并能以中等至极好的收率得到产物。
• Photoredox-Catalyzed Diamidation and Oxidative Amidation of Alkenes: Solvent-Enabled Synthesis of 1,2-Diamides and α-Amino Ketones
  作者：Qixue Qin、Yue-Yue Han、Yan-Yan Jiao、Yanyan He、Shouyun Yu

  DOI：10.1021/acs.orglett.7b01145

  日期：2017.6.2

  Photoredox-catalyzed difunctionalizations of alkenes with O-acyl hydroxylamine derivatives are described. The solvent tunes the outcome of these reactions. Diamidation and oxidative amidation of alkenes can be achieved in CH3CN and DMSO, respectively. A variety of 1,2-diamidates and α-amino ketones bearing many functional groups are prepared using Ir(ppy)3 as the photocatalyst under visible light irradiation

  描述了用O-酰基羟胺衍生物的烯烃的光氧化还原催化的双官能化。溶剂可调节这些反应的结果。烯烃的重氮化和氧化酰胺化可以分别在CH 3 CN和DMSO中实现。以Ir（ppy）3为光催化剂，在可见光照射下，制备了带有多个官能团的1,2-二酰胺和α-氨基酮。
• Hypervalent iodine-mediated oxidative alkene arylation: a thorough analysis
  作者：Liam H. Britt、Zhensheng Zhao、Graham K. Murphy

  DOI：10.1139/cjc-2022-0032

  日期：2022.8.1

  A hypervalent iodine (HVI)-mediated, oxidative alkene arylation reaction has been developed. Both Koser’s reagent (PhI(OH)OTs) and (diacetoxyiodo)toluene (TolI(OAc)₂) were equally viable as oxidants, which reacted with ortho-vinylbiphenyl derivatives to produce tri-, tetra-, and pentacyclic polycyclic aromatic hydrocarbons in yields up to 97%. Comparison of this stoichiometric reaction with a previously reported catalytic process showed that these protocols were largely complementary, and that they likely operate via the same general mechanistic sequence involving vinyliodonium salts decomposing into vinylene phenonium ions. Various mechanistic control experiments were conducted, which ruled out epoxides as intermediates, and which showed that E- and Z-alkene geometry in 10-substituted ortho-vinylbiphenyls had no impact on the ensuing isomeric product distributions. These experiments strongly supported the formation of E-vinyliodonium ions as initial reaction intermediates, and while the occurrence of 1,2-phenyl shift products was a common phenomenon, we concluded that alkyl substitution on the ortho-vinylbiphenyl was a requirement for this alternate pathway to occur.

  我们开发了一种以高价碘 (HVI) 为介质的氧化烯芳基化反应。Koser 试剂（PhI(OH)OTs）和（二乙酰氧基碘）甲苯（TolI(OAc)2）同样可用作氧化剂，它们与正乙烯基联苯衍生物反应生成三环、四环和五环多环芳烃，收率高达 97%。将这一化学反应与之前报道的催化过程进行比较后发现，这两种方法在很大程度上是互补的，它们很可能通过相同的机理顺序进行操作，即乙烯基碘鎓盐分解成乙烯基鎓离子。我们进行了各种机理控制实验，排除了环氧化物作为中间体的可能性，实验结果表明，10-取代正乙烯基联苯中的 E-和 Z-烯几何形状对随后的异构产物分布没有影响。这些实验有力地支持了 E-乙烯基碘离子作为初始反应中间体的形成，虽然 1,2-苯基转变产物的出现是一个普遍现象，但我们得出结论，正乙烯基联苯上的烷基取代是发生这种替代途径的必要条件。