1-(环戊-2-烯-1-基)-4-甲氧基苯 | 31169-38-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-(环戊-2-烯-1-基)-4-甲氧基苯
• 英文名称: 1-(cyclopent-2-en-1-yl)-4-methoxybenzene
• 英文别名: 1-(cyclopent-2-enyl)-4-methoxybenzene；3-(4'-methoxyphenyl)cyclopent-1-ene；3-(4-methoxyphenyl)cyclopentene；3-phenylcyclopentene；4-cyclopent-2-enyl-anisole；(+/-)-Methyl-[4-(cyclopenten-(2)-yl)-phenyl]-aether；3-(p-Methoxyphenyl)-cyclopenten；1-cyclopent-2-en-1-yl-4-methoxybenzene
• CAS: 31169-38-7；38806-00-7
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: XKJNTXNJAJCZGC-UHFFFAOYSA-N

物化性质

• 沸点：
  98-99 °C(Press: 1.1 Torr)
• 密度：
  1.023±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  1-(环戊-2-烯-1-基)-4-甲氧基苯 、 六氯环戊二烯 以 甲苯 为溶剂， 反应 120.0h， 生成 1-<4'-Methoxy-phenyl>-4.5.6.7.10.10-hexachlor-4.7-methylen-2.3.4.7.8.9-hexahydro-inden
  参考文献：
  名称：

  Zur Chemie von Polyhalocyclopentadienen und verwandten Verbindungen, 17. Mitt.: Über die Umsetzung von Hexachlorcyclopentadien mit ungesättigten Verbindungen

  摘要：

  DOI：

  10.1007/bf00903167
• 作为产物：
  描述：

  (E)-1-(2-cyclopropylvinyl)-4-methoxybenzene 在 bis(1,5-cyclooctadiene)nickel (0) 、 二茂铁 、 1,3-双(2,6-二异丙基苯基)咪唑-2-烯 作用下， 以 氘代苯 为溶剂， 生成 1-(环戊-2-烯-1-基)-4-甲氧基苯
  参考文献：
  名称：

  Mechanism of the Ni(0)-Catalyzed Vinylcyclopropane−Cyclopentene Rearrangement

  摘要：

  A combination of physical organic experiments and quantum chemical calculations were used to construct a detailed mechanistic model for the Ni(0)-N-heterocyclic carbene-catalyzed vinylcyclo-propane-cyclopentene rearrangement that involves a mutistep oxidative addition/haptotropic shift/reductive elimination pathway. No evidence for the intermediacy of radicals or zwitterions was found. The roles of substituents on the vinylcyclopropane substrate and variations in the ligands on Ni were evaluated. It is postulated that bulky carbene ligands facilitate formation of the active catalyst species.

  DOI：

  10.1021/jo901525u

文献信息

• A Method for the Net Contra-thermodynamic Isomerization of Cyclic Trisubstituted Alkenes
  作者：Raphaël F. Guignard、Laurent Petit、Samir Z. Zard

  DOI：10.1021/ol4018744

  日期：2013.8.16

  A simple sequence for the net contra-thermodynamic isomerization of cyclic trisubstituted alkenes is reported consisting of a radical addition of p-chlorothiophenol, followed by oxidation to the sulfoxide and thermal syn-elimination to give the least substituted isomeric cycloalkene.

  为环状三取代烯烃的净禁忌热力学异构化的简单序列报道由自由基加成的p -chlorothiophenol，随后氧化成亚砜和热合成β-消除，得到至少取代的同分异构的环烯烃。
• Reaction of diazonium salts with transition metals—III
  作者：K. Kikukawa、K. Nagira、F. Wada、T. Matsuda

  DOI：10.1016/s0040-4020(01)97711-7

  日期：1981.1

  Palladium (0) catalyzed reactions of arenediazonium salts for arylation of aliphatic and cyclic olefins and allylic alcohols, styrene and ethyl acrylate were studied. Effects of the olefinic compounds and other reaction variables on the arylation were presented. Arylpalladium species was proposed as the most plausible intermediated in this reaction.

  研究了钯（0）催化烯丙基二氮杂鎓盐使脂族和环状烯烃与烯丙基醇，苯乙烯和丙烯酸乙酯芳基化的反应。提出了烯烃化合物和其他反应变量对芳基化的影响。有人提出，芳钯是该反应中最合理的中间体。
• Molybdenum(II)-catalyzed alkylation of electron-rich aromatics with allylic acetates
  作者：Andrei V. Malkov、Stuart L. Davis、William L. Mitchell、Pavel Kočovský

  DOI：10.1016/s0040-4039(97)01053-8

  日期：1997.7

  The molybdenum(II) complex [Mo(CO)4Br2]2 has been found to catalyze allylic substitution with aromatic ethers, e.g., anisole (7), as nucleophiles. The reaction is remarkably para-selective (e.g., 7 + 8 → 11).

  已经发现，钼（II）配合物[Mo（CO）4 Br 2 ] 2可以催化芳香族醚，例如苯甲醚（7），作为亲核试剂进行烯丙基取代。该反应明显是对位选择性的（例如7 + 8→11）。
• Heck reaction of aryl halides with linear or cyclic alkenes catalysed by a tetraphosphine/palladium catalyst
  作者：Florian Berthiol、Henri Doucet、Maurice Santelli

  DOI：10.1016/s0040-4039(02)02788-0

  日期：2003.2

  4-Tetrakis(diphenylphosphinomethyl)cyclopentane/[PdCl(C3H5)]2 system catalyses efficiently the Heck reaction of aryl halides with linear alkenes such as pent-1-ene, oct-1-ene or dec-1-ene. Selectivities up to 70% in favour of E-1-arylalk-1-ene isomers can be obtained. In the presence of cyclic alkenes the selectivities of the reactions strongly depends on the ring size. Addition to cyclohexene or cycloheptene led mainly

  cis，cis，cis -1,2,3,4-Tetrakis（diphenylphosphinomethyl）cyclopentane / [PdCl（C 3 H 5）] 2体系有效地催化芳基卤化物与线性烯烃（如戊-1-烯）的Heck反应，辛-1-烯或癸-1-烯。选择性高达赞成70％Ë -1- arylalk -1-烯异构体可制得。在环状烯烃的存在下，反应的选择性很大程度上取决于环的大小。除环己烯或环庚烯外，主要产生1-芳基环烷-3-烯衍生物。另一方面，除环辛烯外，还生成了1-芳基环烷-1-烯加合物。
• Mild Two-Step Process for the Transition-Metal-Free Synthesis of Carbon−Carbon Bonds from Allylic Alcohols/Ethers and Grignard Reagents
  作者：Xinping Han、Yanhua Zhang、Jimmy Wu

  DOI：10.1021/ja100747n

  日期：2010.3.31

  A mild two-step process for the regioselective, transition-metal-free preparation of carbon-carbon bonds from allylic alcohols/ethers and Grignard reagents is described. This process obviates the need for the harsh deprotection conditions usually required for removal of methyl ethers. The synthesis is accomplished by photochemically promoted allylic substitution reactions of allylic alcohols and ethers

  描述了从烯丙醇/醚和格氏试剂中区域选择性、无过渡金属制备碳-碳键的温和两步法。该过程不需要去除甲醚通常所需的苛刻的脱保护条件。该合成是通过烯丙醇和醚与二乙基硫代磷酸的光化学促进的烯丙基取代反应，然后在过渡金属下与各种格氏试剂形成 sp(3)-sp(3) 或 sp(2)-sp(3) 键来完成的。免费条件。根据亲核试剂的性质，可以控制碳-碳键形成事件的区域选择性以提供四级或三级碳中心。