methyl 2-(3-methoxybenzyl)acrylate | 1403496-64-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl 2-(3-methoxybenzyl)acrylate
• 英文别名: Methyl 2-[(3-methoxyphenyl)methyl]prop-2-enoate
• CAS: 1403496-64-9
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: WBEMFRSJVKADAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-(3-methoxybenzyl)acrylate 在 manganese(IV) oxide 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 2-(3-methoxybenzyl)acrylaldehyde
  参考文献：
  名称：

  On the stereochemistry of the Baker's Yeast-mediated reduction of regioisomeric unsaturated aldehydes: Examples of enantioselectivity switch promoted by substrate-engineering

  摘要：

  The Baker's Yeast (BY) reduction of (Z)-2-chloromethyl-3-arylacrylaldehydes was found to afford (R)-2-methyl-3-aryl-propanols showing high enantiomeric excess values. Deuterium incorporation experiments were performed, in order to investigate the mechanism of the bioreduction: the formation of the corresponding substituted 2-benzylacrylaldehydes. as intermediates to be effectively reduced by Baker's Yeast, was suggested. These intermediates were synthesized and submitted to BY reduction to afford the corresponding saturated (R)-alcohols, thus confirming the conclusions drawn from labelling experiments. The enantioselectivity of their bioreduction was found to be opposite with respect to that observed for the corresponding regioisomeric 2-methylcinnamaldehydes. The preparation of the two enantiomers of 2-methyl-3-aryl-propanols by fermentation of two regioisomers represents an interesting example of substrate-controlled enantioselective reaction. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2012.02.003
• 作为产物：
  描述：

  (Z)-methyl 2-(bromomethyl)-3-(3-methoxyphenyl)acrylate 在 三乙烯二胺 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以81%的产率得到methyl 2-(3-methoxybenzyl)acrylate
  参考文献：
  名称：

  On the stereochemistry of the Baker's Yeast-mediated reduction of regioisomeric unsaturated aldehydes: Examples of enantioselectivity switch promoted by substrate-engineering

  摘要：

  The Baker's Yeast (BY) reduction of (Z)-2-chloromethyl-3-arylacrylaldehydes was found to afford (R)-2-methyl-3-aryl-propanols showing high enantiomeric excess values. Deuterium incorporation experiments were performed, in order to investigate the mechanism of the bioreduction: the formation of the corresponding substituted 2-benzylacrylaldehydes. as intermediates to be effectively reduced by Baker's Yeast, was suggested. These intermediates were synthesized and submitted to BY reduction to afford the corresponding saturated (R)-alcohols, thus confirming the conclusions drawn from labelling experiments. The enantioselectivity of their bioreduction was found to be opposite with respect to that observed for the corresponding regioisomeric 2-methylcinnamaldehydes. The preparation of the two enantiomers of 2-methyl-3-aryl-propanols by fermentation of two regioisomers represents an interesting example of substrate-controlled enantioselective reaction. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2012.02.003

文献信息

• Pd-Catalyzed Threefold Arylation of Baylis-Hillman Bromides and Acetates with Triarylbismuth Reagents
  作者：Maddali L. N. Rao、Somnath Giri

  DOI：10.1002/ejoc.201200543

  日期：2012.8

  alkyl 2-benzylacrylates and 2-benzylacrylonitriles were synthesized by means of atom-economic cross-couplings of Baylis–Hillman bromides or acetates with BiAr3 under palladium-catalyzed conditions. These reactions, involving threefold aryl couplings using BiAr3 reagents with bromides and acetates, are fast and are completed in 1–2 h with high product yields.

  在钯催化条件下，通过 Baylis-Hillman 溴化物或乙酸盐与 BiAr3 的原子经济交叉偶联合成了功能化的 2-苄基丙烯酸烷基酯和 2-苄基丙烯腈。这些反应涉及使用 BiAr3 试剂与溴化物和乙酸盐进行三重芳基偶联，反应速度快，在 1-2 小时内完成，产品收率高。
• Substrate-switched dual functionalization of alkenes: catalyst-free synthetic route for β-hydroxy and β-keto thioethers
  作者：Satpal Singh Badsara、Pratibha Singh、Rakhee Choudhary、Rekha Bai、Mahesh C. Sharma

  DOI：10.1039/c9nj02682g

  日期：——

  In this study, a substrate-controlled dual functionalization of alkenes under catalyst-free and solvent-free conditions is described. Alkenes possessing different electron-withdrawing groups, namely, ester and nitrile, reacted with a variety of thiols under air to provide β-hydroxy thioethers and β-keto thioethers, respectively, in good to excellent yields.

  在这项研究中，描述了在无催化剂和无溶剂条件下烯烃的底物控制的双官能化。具有不同吸电子基团（即酯和腈）的烯烃与多种硫醇在空气中反应，分别以良好或优异的收率提供β-羟基硫醚和β-酮硫醚。