methyl 2-((3,5-difluorophenyl)(hydroxy)methyl)acrylate

• 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: methyl 2-((3,5-difluorophenyl)(hydroxy)methyl)acrylate
• 英文别名: methyl 2-[(3,5-difluorophenyl)(hydroxy)methyl]prop-2-enoate；Methyl 2-[(3,5-difluorophenyl)-hydroxymethyl]prop-2-enoate
• 化学式: C₁₁H₁₀F₂O₃
• 分子量: 228.195
• InChiKey: XSYPSMKGYMKLME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-((3,5-difluorophenyl)(hydroxy)methyl)acrylate 在 氢溴酸 、 溶剂黄146 作用下， 反应 1.0h， 以89%的产率得到(Z)-methyl 2-(bromomethyl)-3-(3,5-difluorophenyl)acrylate
  参考文献：
  名称：

  Syntheses of β- and γ-fluorophenyl cis- and trans-α-methylene-γ-butyrolactones

  摘要：

  Preparation of a series of cis-gamma-fluorophenyl-beta-phenyl-alpha-methylene-gamma-butyrolactones is reported via 'allylboration' of fluorobenzaldehydes with (E)-methyl 3-phenyl-2-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)acrylate. The corresponding trans-gamma-fluorophenyl lactones were prepared either (i) via 'allylboration' using the (Z)-reagents or (ii) via an indium triflate-mediated isomerization of the cis-products. The difficulty in isomerizing difluorinated cis-products confirms the probable intermediacy of carbocations. Finally, the synthesis of cis-beta-fluorophenyl-gamma-phenyl-alpha-methylene-gamma-butyrolactones was achieved via an indium-catalyzed allylation-lactonization of aldehydes with (Z)-2-(bromomethyl)-3-(fluorophenyl)acrylates. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.07.106
• 作为产物：
  描述：

  3,5-二氟苯甲醛 、 丙烯酸甲酯（MA） 在 三乙烯二胺 作用下， 以91%的产率得到methyl 2-((3,5-difluorophenyl)(hydroxy)methyl)acrylate
  参考文献：
  名称：

  1,1'-羰基二咪唑介导了森田-贝利斯-希尔曼加合物的N-取代咪唑衍生物的合成

  摘要：

  在这封信中，我们描述了一种简单而直接的合成N-取代的咪唑衍生物的方法。1,1-羰基二咪唑介导了该过程，该过程不需要活化基团步骤。我们以高收率和短反应时间获得了咪唑衍生物。为了证明上述化合物的合成意义，我们还描述了由这些衍生物合成新型离子液体的方法。

  DOI：

  10.1016/j.tetlet.2013.10.146

文献信息

• Transition-Metal-Free Cascade Synthesis of 4-Quinolones: Umpolung of Michael Acceptors via Ene Reaction with Arynes
  作者：R. Santhosh Reddy、Chandraiah Lagishetti、I. N. Chaithanya Kiran、Hengyao You、Yun He

  DOI：10.1021/acs.orglett.6b01830

  日期：2016.8.5

  adducts through a cascade sequence involving an insertion/cyclization/ene reaction process to afford 4-quinolones in high yields with a broad substrate scope under mild reaction conditions. Essentially, an umpolung of reactivity at the β carbon of α,β-unsaturated ketone has been achieved by an inverse electron demand aryne–ene reaction to provide a C-arylated product.

  描述了一种新颖的“一锅”芳烃转化，该转化可提供各种4-喹诺酮衍生物，而无需借助过渡金属催化。Arynes与aza-Morita–Baylis–Hillman（AMBH）加合物通过级联序列反应，涉及插入/环化/烯反应过程，从而在温和的反应条件下以高收率提供高产的4-喹诺酮类化合物。本质上，在α，β不饱和酮的β碳反应性的极性转换已经由逆电子需求芳炔-烯反应来实现，以提供Ç -arylated产物。
• Ozonolysis of Morita–Baylis–Hillman adducts originated from aromatic aldehydes: an expeditious diastereoselective approach for the preparation of α,β-dihydroxy-esters
  作者：Carlos A.M. Abella、Patrícia Rezende、Michele F. Lino de Souza、Fernando Coelho

  DOI：10.1016/j.tetlet.2007.10.149

  日期：2008.1

  We disclose herein ozonolysis of Morita-Baylis-Hillman adducts originated from aromatic aldehydes. This efficient reaction provides alpha-ketoesters with different substitution patterns on the aromatic ring. Diastercoselective reduction of the corresponding alpha-ketoester obtained in the oxidative cleavage step provides alpha,beta-dihydroxy-esters with excellent degree of anti diastereoselection. The method is simple and easy to execute and is therefore a valuable alternative to prepare either alpha-ketoesters or alpha-dihydroxy-esters. (c) 2007 Elsevier Ltd. All rights reserved.
• Nájera oxime-derived palladacycles catalyze intermolecular Heck reaction with Morita–Baylis–Hillman adducts. An improved and highly efficient synthesis of α-benzyl-β-ketoesters
  作者：Bruno R.V. Ferreira、Rodrigo V. Pirovani、Luis G. Souza-Filho、Fernando Coelho

  DOI：10.1016/j.tet.2009.06.084

  日期：2009.9

  An improved and highly efficient synthesis of several alpha-benzyl-beta-ketoesters from Morita-Baylis-Hillman adducts is described. These adducts were used as substrates for an intermolecular Heck reaction catalyzed by a Najera oxime-derived palladacycles. These efficient catalytic conditions probed to be very selective providing only the corresponding functionalized beta-ketoesters in high yield with no decarboxylation product. It seems that the method herein described is one of the most efficient for the synthesis of alpha-benzyl-beta-ketoesters. (C) 2009 Elsevier Ltd. All rights reserved.