1-methoxy-4-(2-methoxyvinyl)benzene | 64304-84-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-methoxy-4-(2-methoxyvinyl)benzene
• 英文别名: (Z)-1-methoxy-4-(2-methoxyvinyl)benzene；1-methoxy-4-[(Z)-2-methoxyethenyl]benzene
• CAS: 64304-84-3
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: OGUXYWOIPQQGKA-FPLPWBNLSA-N

物化性质

• 沸点：
  100-120 °C(Press: 19 Torr)
• 密度：
  1.021±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methoxy-4-(2-methoxyvinyl)benzene 在 硫酸 、 氧气 、 tetraphenylporphyrin 作用下， 生成 6-Methoxy-2,3,3a,8a-tetrahydro-benzo[b]furo[3,2-d]furan-2-ol
  参考文献：
  名称：

  Matsumoto, Masakatsu; Kuroda, Keiko, Angewandte Chemie, 1982, vol. 94, # 5, p. 376 - 377

  摘要：

  DOI：
• 作为产物：
  描述：

  2-methoxy-3-(4-methoxyphenyl)-2-propenoic acid 在 copper(II) carbonate 作用下， 以 N,N-二甲基乙酰胺 、 二甲基亚砜 为溶剂， 反应 12.0h， 生成 1-methoxy-4-(2-methoxyvinyl)benzene
  参考文献：
  名称：

  Pd-Catalyzed Regioselective Decarboxylative/C–H α-Alkoxyalkenylation of Heterocycles Using α-Carboxyvinylethers

  摘要：

  A direct introduction of vinyl ethers into C-H bond of heterocycles is reported. For this purpose, decarboxylative direct C-H cross-coupling of 1,3-diazoles with alpha-carboxyvinyl ethers as coupling partners was achieved under Pd(0)/Cu(I) cooperative catalysis to produce various alpha-heteroarylated vinylethers. This methodology was applied to the innovative production of heteroarylated enolizable ketones and naturally occurring bis-oxa(thia)zoles.

  DOI：

  10.1021/acscatal.7b01330

文献信息

• Cyclopropanation of alkenes with metallocarbenes generated from monocarbonyl iodonium ylides
  作者：Tristan Chidley、Graham K. Murphy

  DOI：10.1039/c8ob02636j

  日期：——

  Reacting Wittig reagents and the hypervalent iodine reagent iodosotoluene, in the presence of 10 mol% Cu(tfacac)2 and 5 equiv. of alkene, results in a novel cyclopropanation reaction. The reagent combination is believed to generate a transient monocarbonyl iodonium ylide (MCIY) in situ, which can be intercepted by the copper catalyst to give a metallocarbene. Both ester and ketone derived phosphoranes

  在10摩尔％Cu（tfacac）2和5当量的存在下，使Wittig试剂和高价碘试剂碘代甲苯反应。烯的合成导致新的环丙烷化反应。据信，该试剂组合可在原位产生瞬态单羰基碘鎓内鎓盐（MCIY），可被铜催化剂拦截以生成金属卡宾。可以使用酯和酮衍生的膦烷，也可以使用苯乙烯基和非苯乙烯基的烯烃，后者可提供高达81％的收率的环丙烷。
• Nickel-Catalyzed System for the Cross-Coupling of Alkenyl Methyl Ethers with Grignard Reagents under Mild Conditions
  作者：Thomas Hostier、Zeina Neouchy、Vincent Ferey、Domingo Gomez Pardo、Janine Cossy

  DOI：10.1021/acs.orglett.8b00313

  日期：2018.4.6

  A nickel-catalyzed cross-coupling of alkenyl methyl ethers with Grignard reagents, under mild conditions, is described. These conditions allowed access to various stilbenes and heterocyclic stilbenic derivatives as well as to a potential anticancer agent DMU-212.

  描述了在温和条件下镍催化的链烯基甲基醚与格利雅试剂的交叉偶联。这些条件允许获得各种斯蒂芬烯和杂环斯蒂芬烯衍生物以及潜在的抗癌剂DMU-212。
• Synthesis of Substrates for Aldolase-Catalysed Reactions: A Comparison of Methods for the Synthesis of Substituted Phenylacetaldehydes
  作者：Derar Al-Smadi、Thilak Enugala、Thomas Norberg、Jan Kihlberg、Mikael Widersten

  DOI：10.1055/s-0036-1591963

  日期：2018.6

  Methods for the synthesis of phenylacetaldehydes (oxidation, one-carbon chain extension) were compared by using the synthesis of 4-methoxyphenylacetaldehyde as a model example. Oxidations of 4-methoxyphenylethanol with activated DMSO (Swern oxidation) or manganese dioxide gave unsatisfactory results; whereas oxidation with 2-iodoxybenzoic acid (IBX) produced 4-methoxyphenylacetaldehyde in reasonable

  以4-甲氧基苯乙醛的合成为例，比较了苯乙醛的合成方法（氧化、单碳链延长）。用活化的 DMSO（Swern 氧化）或二氧化锰氧化 4-甲氧基苯基乙醇的结果不令人满意；而用 2-碘氧基苯甲酸 (IBX) 氧化以合理 (75%) 的产率生成 4-甲氧基苯基乙醛。然而，用甲氧基亚甲基-三苯基膦进行 Wittig 型单碳链扩展，然后水解，从 4-甲氧基苯甲醛（一种廉价的起始材料）得到 4-甲氧基苯乙醛的产率非常高（总产率为 81%）。该方法随后被用于合成一组 10 种取代的苯乙醛，收率非常好。
• Titanium-catalyzed highly stereoselective anti-Markovnikov intermolecular hydroalkoxylation of alkynes to prepare <i>Z</i>-enol ethers
  作者：Yang Wang、Biao Ma、Yingning Mao、Zhihui Wang、Jinsong Peng、Chunxia Chen、Zhanyu Li

  DOI：10.1039/d3ob01514a

  日期：——

  Enol ethers are essential synthetic frameworks and widely applied in organic synthesis; however, high regio- and stereo-selective access to enol ethers remains challenging. Herein, we report a titanium-catalyzed stereospecific anti-Markovnikov hydroalkoxylation reaction of alkynes for the synthesis of Z-enol ethers with excellent functional group tolerance and yields. Mechanistic studies showed that

  烯醇醚是重要的合成骨架，广泛应用于有机合成；然而，高区域和立体选择性获得烯醇醚仍然具有挑战性。在此，我们报道了钛催化的炔烃的立体特异性反马尔可夫尼科夫加氢烷氧基化反应，用于合成具有优异官能团耐受性和产率的Z-烯醇醚。机理研究表明，钛与炔烃配位，然后氧阴离子从背面攻击炔烃的π键，提供反式氧金属化中间体，这解释了高Z立体选择性。此外， Z-烯醇醚可以作为一种合成子用于后期转化和克级合成，这表明了它们在有机合成中的潜在价值。
• Carbenoid versus Vinylogous Reactivity in Rhodium(II)-Stabilized Vinylcarbenoids
  作者：Huw M. L. Davies、Baihua Hu、Elie Saikali、Paul R. Bruzinski

  DOI：10.1021/jo00095a031

  日期：1994.8

  Rhodium(II)-stabilized vinylcarbenoid intermediates display electrophilic character at both the carbenoid site and the vinylogous position. The solvent and catalyst as well as the vinylcarbenoid structure have major effects on the regiochemical outcome of the reaction of vinylcarbenoids with alkenes and dienes. Reaction of vinylcarbenoids with vinyl ethers can lead to the formation of either cyclopropanes or cyclopentenes while reaction of vinylcarbenoids with cyclopentadiene can lead to the formation of either bicyclo[3.2.1]octadiene or bicyclo[2.2.1]heptene derivatives.