(E)-methyl 3-methoxy-2-(2-(benzyloxy)phenyl)acrylate | 103497-78-5

• 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: (E)-methyl 3-methoxy-2-(2-(benzyloxy)phenyl)acrylate
• 英文别名: (E)-3-methoxy-2-(2-benzyloxyphenyl)acrylic acid methyl ester；(E)-methyl 2-(2-(benzyloxy)phenyl)-3-methoxyacrylate；methyl (E)-2-(2-benzyloxy)phenyl-3-methoxyacrylate；E-methyl 3-methoxy-2-(2'-benzyloxyphenyl)propenoate；Methyl 2-(2-(benzyloxy)phenyl)-3-methoxyacrylate；methyl (E)-3-methoxy-2-(2-phenylmethoxyphenyl)prop-2-enoate
• CAS: 103497-78-5
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: IZBMTHOGHLZLSY-DTQAZKPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-methyl 3-methoxy-2-(2-(benzyloxy)phenyl)acrylate 在 10% palladium on activated carbon 、 氢气 、 caesium carbonate 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 85.0 ℃ 、405.33 kPa 条件下， 反应 9.0h， 生成 (E)-methyl 3-methoxy-2-(2-(6-phenoxypyrimidin-4-yloxy)phenyl)acrylate
  参考文献：
  名称：

  Concise and modular synthesis of regioisomeric haptens for the production of high-affinity and stereoselective antibodies to the strobilurin azoxystrobin

  摘要：

  The immune response to regioisomeric haptens of azoxystrobin with varied derivatization sites was studied. Based on the Sonogashira and Suzuki-Miyaura couplings and following a straightforward modular design, we have synthesized four haptens with the same linker anchored through C-C bonds and located at different sites of the molecule. The most stereoselective antibodies were produced from immunogens with the spacer arm at a distal position from the beta-methoxyacrylate moiety characteristic of strobilurins. Moreover, we observed that assay cross-reactivity was reliant on the functionalization site of the competitor derivative. Finally, the antibody binding site was explored using synthetic chemical analogues. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2010.11.054
• 作为产物：
  描述：

  2-羟基苯乙酸甲酯 在 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 (E)-methyl 3-methoxy-2-(2-(benzyloxy)phenyl)acrylate
  参考文献：
  名称：

  JP5690514

  摘要：

  公开号：

文献信息

• Fungicides
  申请人：Imperial Chemical Industries PLC

  公开号：US05286894A1

  公开（公告）日：1994-02-15

  This invention relates to derivatives of acrylic acid useful as fungicides, to processes for preparing them, to fungicidal compositions containing them, and to methods of combating fungi, especially fungal infections in plants, using them.

  这项发明涉及丙烯酸衍生物，其作为杀真菌剂有用，涉及制备它们的方法，含有它们的杀真菌组合物，以及使用它们来对抗真菌，特别是在植物中使用它们来对抗真菌感染的方法。
• Esters of 2-phenylalkanenitriles and antifungal compositions containing them
  申请人：Stoutamire Donald Wesley

  公开号：US20080153905A1

  公开（公告）日：2008-06-26

  Esters of 2-phenylalkanenitriles, such as 3-acetoxy-2-(2-chloro-5-(difluoromethoxy)phenyl)propanenitrile and 3-acetoxy-2-(4-chlorophenyl)propanenitrile, and compositions containing such esters, are useful as fungicides at very low concentrations.

  2-苯基烷基腈的酯，如3-乙氧基-2-(2-氯-5-(二氟甲氧基)苯基)丙腈和3-乙氧基-2-(4-氯苯基)丙腈，以及含有这些酯的组合物，在极低浓度下作为杀真菌剂是有用的。
• 一种基于Suzuki反应制备嘧菌酯的方法
  申请人：东华大学

  公开号：CN105566231A

  公开（公告）日：2016-05-11

  本发明涉及一种基于Suzuki反应制备嘧菌酯的方法，包括：将(E)-2-[2-(6-氯嘧啶-4-基氧基)苯基]-3-甲氧基丙烯酸甲酯、碳酸铯、水杨腈按摩尔比1:2:2组成的混合物溶于溶剂中，N2保护，于85℃下搅拌7h，分离提纯，即得。本发明提出一种新型绿色合成嘧菌酯低成本及高产率的合成方法，且该法工艺简单，适合大生产。
• A Concise Synthesis of Azoxystrobin using a Suzuki Cross-Coupling Reaction
  作者：Yong-Gan Liu、Yan Luo、Yao Lu

  DOI：10.3184/174751915x14418863197125

  日期：2015.10

  A simple, efficient and eco-friendly process for the synthesis in good yield of azoxystrobin from 2-bromophenol has been developed using phenolic hydroxyl protection, Grignard reaction, Suzuki cross-coupling, hydrogenation and a nucleophilic reaction on a 2-chloropyrimidine.

  利用酚羟基保护、格氏反应、铃木交叉偶联、氢化和 2-氯嘧啶的亲核反应，开发出了一种简单、高效和环保的工艺，可从 2-溴苯酚合成唑啉草酯，且收率高。
• Certain 2-pyridyl oxy-phenyl acrylates having fungicidal, insecticidal,
  申请人：Imperial Chemical Industries PLC

  公开号：US05057146A1

  公开（公告）日：1991-10-15

  This invention relates to derivatives of acrylic acid useful in agriculture (especially as fungicides but also as plant growth regulators, insecticides and nematocides), to processes for preparing them, to agricultural (especially fungicidal) compositions containing them, and to methods of using them to combat fungi, especially fungal infections in plants, to regulate plant growth and to kill or control insect or nematode pests. The invention provides a compound having the formula (I): ##STR1## and stereoisomers thereof, wherein W is a substituted pyridinyl or substituted pyrimidinyl group linked to A by any of its ring carbon atoms; A is either an oxygen atom or S(O).sub.n wherein n is 0, 1 or 2; X, Y and Z, which are the same or different, are hydrogen or halogen atoms, or hydroxy, optionally substituted alkyl (including haloalkyl), optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, (including haloalkoxy), optionally substituted alkylthio, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted acyloxy, optionally substituted amino, optionally substituted acylamino, nitro, cyano, --CO.sub.2 R.sup.3, --CONR.sup.4 R.sup.5, --COR.sup.6 or --S(O).sub.m R.sup.7 (wherein m is 0, 1 or 2) groups, or any two of the groups X, Y and Z, when they are in adjacent positions on the phenyl ring, may join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; R.sup.1 and R.sup.2, which are the same or different, are optionally substituted alkyl (including fluoroalkyl) groups provided that when W is 5-trifluoromethylpyridin-2-yl, A is oxygen, X is hydrogen, and R.sup.1 and R.sup.2 are both methyl, Y and Z are not both hydrogen, Y is not F, Cl, methyl, nitro, 5--CF.sub.3, 5--SCH.sub.3 or 4--(CH.sub.3).sub.2 N if Z is hydrogen and Y and Z together are not 3-nitro-5-chloro, 3,5-dinitro, 4,5-dimethoxy or 4,5-methylenedioxy; and R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7, which are the same or different, are hydrogen atoms or optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl or optionally substituted aralkyl groups; and metal complexes thereof.

  本发明涉及丙烯酸的衍生物，其在农业中有用（特别是作为杀菌剂，但也作为植物生长调节剂、杀虫剂和线虫剂），以及制备它们的过程，包含它们的农业（特别是杀菌剂）组合物，以及使用它们来对抗真菌，特别是植物中的真菌感染，调节植物生长，以及杀死或控制昆虫或线虫害的方法。本发明提供了一个化合物，其化学式为（I）：##STR1##及其立体异构体，其中W是被任何环碳原子连接到A的取代吡啶基或取代嘧啶基；A是氧原子或S（O）.sub.n，其中n为0，1或2；X、Y和Z，它们相同或不同，是氢或卤素原子，或羟基、可选取代的烷基（包括卤代烷基）、可选取代的烯基、可选取代的炔基、可选取代的烷氧基（包括卤代烷氧基）、可选取代的烷硫基、可选取代的芳氧基、可选取代的芳基烷氧基、可选取代的酰氧基、可选取代的氨基、可选取代的酰胺基、硝基、氰基、--CO.sub.2R.sup.3、--CONR.sup.4R.sup.5、--COR.sup.6或--S（O）.sub.mR.sup.7（其中m为0、1或2）基团，或当它们在苯环上相邻的位置时，X、Y和Z中的任意两个基团可以连接形成一个融合环，可以是芳香族或脂环，可选包含一个或多个杂原子；R.sup.1和R.sup.2，它们相同或不同，是可选取代的烷基（包括氟代烷基）基团，但当W为5-三氟甲基吡啶-2-基时，A为氧，X为氢，R.sup.1和R.sup.2均为甲基，Y和Z不同时为氢，Y不为F、Cl、甲基、硝基、5--CF.sub.3、5--SCH.sub.3或4--（CH.sub.3）.sub.2N，如果Z为氢，则Y和Z一起不为3-硝基-5-氯、3,5-二硝基、4,5-二甲氧基或4,5-亚甲基二氧基；以及它们的金属配合物。