methyl 2-methoxy-5-(4-tolyl)furan-3-carboxylate | 161008-04-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: methyl 2-methoxy-5-(4-tolyl)furan-3-carboxylate
• 英文别名: 2-methoxy-3-methoxycarbonyl-5-(p-tolyl)furan；Methyl 2-methoxy-5-(4-methylphenyl)-3-furancarboxylate；methyl 2-methoxy-5-(4-methylphenyl)furan-3-carboxylate
• CAS: 161008-04-4
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: DATALFMCYDVEPM-UHFFFAOYSA-N

物化性质

• 熔点：
  107-108 °C(Solv: ligroine (8032-32-4); ethyl ether (60-29-7))
• 沸点：
  363.3±42.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-methoxy-5-(4-tolyl)furan-3-carboxylate 在 乙醛肟 、 乙硫醚 、 氧气 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 Methyl 3-(4-methylphenyl)-6-oxooxazine-5-carboxylate
  参考文献：
  名称：

  Iesce, M. Rosaria; Cermola, Flavio; Guitto, Antonio, Synlett, 1999, # 4, p. 417 - 418

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 2-(p-toluoylamino)propionate 在 五氯化磷 作用下， 生成 methyl 2-methoxy-5-(4-tolyl)furan-3-carboxylate
  参考文献：
  名称：

  Iesce, M. Rosaria; Cermola, Flavio; Giordano, Federico, Journal of the Chemical Society. Perkin transactions I, 1994, # 22, p. 3295 - 3298

  摘要：

  DOI：

文献信息

• Photooxygenation of furans in water and ionic liquid solutions
  作者：Anna Astarita、Flavio Cermola、Marina DellaGreca、Maria Rosaria Iesce、Lucio Previtera、Maria Rubino

  DOI：10.1039/b914726h

  日期：——

  Photooxygenation of differently functionalized furans is investigated in aqueous solutions and in ionic liquids [emim]Br and [bmim]BF4. The reaction is generally selective and the final products derive from rearrangement of the intermediate endoperoxides, depending mainly on the polarity and/or nucleophilic nature of the solvent.

  不同官能化的呋喃在水溶液及离子液体[emim]Br和[bmim]BF4中的光氧氧化反应被研究。该反应通常具有选择性，最终产物源自中间过氧化物的重排，主要取决于溶剂的极性和/或亲核性质。
• Photosensitized Oxidation of Furans; Part 18: A Simple Method for a One-Pot Synthesis of Functionalized Methyl cis-4-Oxoalk-2-enoates
  作者：M. Rosaria Iesce、Flavio Cermola、Alfonso Piazza、Rachele Scarpati、M. Liliana Graziano

  DOI：10.1055/s-1995-3922

  日期：1995.4

  Functionalized methyl cis-4-oxoalk-2-enoates 2 are synthesized in a one-pot procedure by singlet oxygen oxygenation of the corresponding 2-methoxyfurans 1 in methanol and reduction of the resulting hydroperoxides 4 and 5 by the sulfides 6 which are selectively oxidized into the sulfoxides 7. The synthetic method has a wide range of applicability and affords compounds 2 stereoselectively and in good yields; concomitantly the sulfoxides 7 are obtained in excellent yields.

  功能化的甲基顺-4-氧烯-2-酸酯2通过单氧对相应的2-甲氧基呋喃1在甲醇中的氧化，随后用硫化物6选择性还原生成的过氧化物4和5，采用一锅法合成。该合成方法具有广泛的适用性，能够立体选择性地高产量地获得化合物2；同时，亚砜7也以优异的产率获得。
• The first nucleophilic aromatic substitution of suitably activated 2-methoxyfurans with Grignard reagents
  作者：M.Rosaria Iesce、M.Liliana Graziano、Flavio Cermola、Stefania Montella、Lucrezia Di Gioia

  DOI：10.1016/s0040-4039(03)01430-8

  日期：2003.7

  The reaction of 2-methoxyfuroates 1 with Grignard reagents 2 leads to tertiary alcohols or SNAr products depending on the position of the alkoxycarbonyl group. OMe-Displacement occurs only for 3-substituted derivatives. It takes place even for 3-acetyl-2-methoxyfuran while the presence of a further ester function at 4 position induces the formation of the sole 4-tertiary alcohol. The OMe-substitution

  2- methoxyfuroates反应1与格氏试剂2个通向叔醇或S ñ取决于烷氧基羰基的位置氩产品。OMe位移仅发生在3取代的衍生物上。即使对于3-乙酰基-2-甲氧基呋喃，它也发生，而在4位上进一步的酯官能团的存在诱导了唯一的4-叔醇的形成。已经证实了OMe取代具有广泛的呋喃和Grignard试剂，并且仅在与作为离域阴离子的苄基和烯丙基试剂的反应中发现了低收率。给出了机械解释。
• Catalyst-Controlled Ring-Opening Cycloisomerization Reactions of Cyclopropenyl Carboxylates for Highly Regioselective Synthesis of Different 2-Alkoxyfurans
  作者：Jie Chen、Shengming Ma

  DOI：10.1002/asia.201000324

  日期：2010.11.2

  Differently substituted 2‐alkoxyfurans (2,3,4‐ or 2,3,5‐trisubstituted furans) were highly regioselectively synthesized by means of the ring‐opening cycloisomerization of the same cyclopropenyl carboxylates with good yields in different solvents and excellent regioselectivity by using [Cu(acac)2] (acac=acetylacetonate) or [RuCl2(PPh3)3] as the catalyst, respectively. The structures of these two different

  通过相同环丙烯基羧酸酯的开环环异构化，在不同溶剂中具有良好的收率，并通过使用优异的区域选择性，可以高度区域选择性地合成不同取代的2-烷氧基呋喃（2,3,4-或2,3,5-三取代呋喃）分别作为催化剂的[Cu（acac）2 ]（acac =乙酰丙酮）或[RuCl 2（PPh 3）3 ]。这两种不同类型的呋喃的结构是通过X射线衍射研究确定的。已经提出了基本原理。
• Carbonyl Oxide Chemistry. 6.¹ <i>N</i>-(Hydroperoxyalkyl)keto Nitrones and α-Oxime Ether Hydroperoxides via Disubstituted Carbonyl Oxides and Oximes
  作者：M. Rosaria Iesce、Flavio Cermola、Antonio Guitto

  DOI：10.1021/jo9806916

  日期：1998.12.1