(Z)-ethyl 3-(3-methoxyphenyl)acrylate | 1001022-76-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-ethyl 3-(3-methoxyphenyl)acrylate
• 英文别名: ethyl (Z)-3-(3-methoxyphenyl)prop-2-enoate
• CAS: 1001022-76-9
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: UPOMPRQKAGEXPN-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：

  (Z)-ethyl 3-(3-methoxyphenyl)acrylate 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以90%的产率得到cis-3-methoxycinnamic acid
  参考文献：
  名称：

  Substituent effects of cis-cinnamic acid analogues as plant growh inhibitors

  摘要：

  1-O-cis-Cinnamoyl-beta-D-glucopyranose is one of the most potent allelochemicals that has been isolated from Spiraea thunbergii Sieb by Hiradate et al. It derives its strong inhibitory activity from cis-cinnamic acid (cis-CA), which is crucial for phytotoxicity. By preparing and assaying a series of cis-CA analogues, it was previously found that the key features of cis-CA for lettuce root growth inhibition are a phenyl ring, cis-configuration of the alkene moiety, and carboxylic acid. On the basis of a structure-activity relationship study, the substituent effects on the aromatic ring of cis-CA were examined by systematic synthesis and the lettuce root growth inhibition assay of a series of cis-CA analogues having substituents on the aromatic ring. While ortho- and para-substituted analogues exhibited low potency in most cases, meta-substitution was not critical for potency, and analogues having a hydrophobic and sterically small substituent were more likely to be potent. Finally, several cis-CA analogues were found to be more potent root growth inhibitors than cis-CA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.08.013
• 作为产物：
  描述：

  3-甲氧基苯甲醛 、 ethyl 2-[bis(2-isopropylphenoxy)phosphoryl]acetate 在 苄基三甲基氢氧化铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以88%的产率得到(Z)-ethyl 3-(3-methoxyphenyl)acrylate
  参考文献：
  名称：

  Substituent effects of cis-cinnamic acid analogues as plant growh inhibitors

  摘要：

  1-O-cis-Cinnamoyl-beta-D-glucopyranose is one of the most potent allelochemicals that has been isolated from Spiraea thunbergii Sieb by Hiradate et al. It derives its strong inhibitory activity from cis-cinnamic acid (cis-CA), which is crucial for phytotoxicity. By preparing and assaying a series of cis-CA analogues, it was previously found that the key features of cis-CA for lettuce root growth inhibition are a phenyl ring, cis-configuration of the alkene moiety, and carboxylic acid. On the basis of a structure-activity relationship study, the substituent effects on the aromatic ring of cis-CA were examined by systematic synthesis and the lettuce root growth inhibition assay of a series of cis-CA analogues having substituents on the aromatic ring. While ortho- and para-substituted analogues exhibited low potency in most cases, meta-substitution was not critical for potency, and analogues having a hydrophobic and sterically small substituent were more likely to be potent. Finally, several cis-CA analogues were found to be more potent root growth inhibitors than cis-CA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.08.013

文献信息

• One-Pot Synthesis of α,β-Unsaturated Esters, Ketones, and Nitriles from Alcohols and Phosphonium Salts
  作者：Xiaochun Yu、Shun Wang、Weijie Ding、Juan Hu、Huile Jin

  DOI：10.1055/s-0036-1590904

  日期：2018.1

  reacted not only with benzylic and heteroaromatic alcohols, but also with aliphatic alcohols, forming the corresponding α,β-unsaturated esters, ketones, and nitriles in moderate to excellent yields. A general method for the synthesis of α,β-unsaturated esters, ketones, and nitriles is successfully achieved by a one-pot copper-catalyzed oxidation with O2 in air as oxidant. The solvent mixture of acetonitrile

  摘要 通过在空气中以O 2为氧化剂的一锅铜催化氧化成功地实现了合成α，β-不饱和酯，酮和腈的通用方法。乙腈和甲酰胺（1：1）的溶剂混合物经过优化，可确保在一锅中有效地进行醇类的氧化，de盐的去质子化和Wittig反应。已针对该方法探索了广泛的底物，包括三个吸电子基团（CO 2 Et，COPh，CN）官能化的salts盐。它们不仅与苄基和杂芳族醇反应，而且与脂族醇反应，以中等至极好的收率形成相应的α，β-不饱和酯，酮和腈。 通过在空气中以O 2为氧化剂的一锅铜催化氧化成功地实现了合成α，β-不饱和酯，酮和腈的通用方法。乙腈和甲酰胺（1：1）的溶剂混合物经过优化，可确保在一锅中有效地进行醇类的氧化，de盐的去质子化和Wittig反应。已针对该方法探索了广泛的底物，包括三个吸电子基团（CO 2 Et，COPh，CN）官能化的salts盐。它们不仅与苄基和杂芳族醇反应，而且与脂族醇反应，以中等至极
• Silver-Catalyzed Cross-Olefination of Donor and Acceptor Diazo Compounds: Use of<i>N</i>-Nosylhydrazones as Diazo Surrogate
  作者：Zhaohong Liu、Binbin Liu、Xue-Feng Zhao、Yan-Bo Wu、Xihe Bi

  DOI：10.1002/ejoc.201601610

  日期：2017.1.26

  The cross-olefination reaction of donor and acceptor diazo compounds is reported. The use of N-nosylhydrazones as the diazo surrogates and the dependence on silver catalysis are crucial for the reaction development. A variety of (hetero)aryl N-nosylhydrazones and α-diazo esters, amides, and phosphonates were compatible, affording functionalized alkenes in good-to-high yields with moderate Z/E selectivity

  报道了供体和受体重氮化合物的交叉烯烃化反应。使用 N-nosylhydrazones 作为重氮替代物和对银催化的依赖对于反应发展至关重要。各种（杂）芳基 N-nosylhydrazones 和 α-重氮酯、酰胺和膦酸酯是相容的，以良好到高的产率提供功能化烯烃，Z/E 选择性适中。实验和 DFT 计算结果表明交叉选择性是由于银催化剂对供体重氮化合物的选择性活化。
• <i>Z</i>-Selective Horner–Wadsworth–Emmons-type Reaction Using a 10-P-5 Phosphorane Bearing Bidentates Derived from 1-Naphthol
  作者：Satoshi Kojima、Jun-ya Arimura、Kazumasa Kajiyama

  DOI：10.1246/cl.2010.1138

  日期：2010.11.5

  A Horner–Wadsworth–Emmons-type 10-P-5 phosphorane reagent bearing bidentate ligands from 1-naphthol was prepared and examined in the olefination of aldehydes. Z-Selectivity was generally high except for the case of 3-phenylpropanal, and acetophenone was also found to react with relatively high selectivity.

  一种含有双齿配体的10-P-5膦杂环戊二烯试剂，源自1-萘酚，被制备并用于醛的不对称烯化反应中进行了研究。一般情况下，Z-选择性较高，除了3-苯基丙醛的情况，同时发现乙酰苯也能够以相对高的选择性发生反应。
• BF₃·OEt₂-mediated syn-selective Meyer–Schuster rearrangement of phenoxy propargyl alcohols for Z-β-aryl-α,β-unsaturated esters
  作者：Surendra Puri、Madala Hari Babu、Maddi Sridhar Reddy

  DOI：10.1039/c6ob01090c

  日期：——

  1-aryl-3-phenoxy propargyl alcohols is achieved via a BF3-mediated syn-selective Meyer–Schuster rearrangement under ambient conditions. The reaction mechanism is postulated to involve an electrophilic borylation of an allene intermediate as the key step to kinetically control the stereoselectivity.

  通过在环境条件下通过BF 3介导的顺选择性Meyer-Schuster重排，可以从容易获得的1-芳基-3-苯氧基炔丙基醇合成Z -β-芳基-α，β-不饱和酯。假定该反应机理涉及丙二烯中间体的亲电子硼化，这是动力学控制立体选择性的关键步骤。
• Pd(OAc)₂/[C₁₈–DABCO–C₁₈]2Br: a nano palladium catalytic approach for Mizoroki–Heck and Suzuki–Miyaura coupling reactions in water
  作者：Archana Rajmane、Chunilal Pawara、Sumit Kamble、Utkarsh More、Suresh Patil、Arjun Kumbhar

  DOI：10.1039/d3nj04035f

  日期：——

  Similarly, the catalytic system was highly efficient in Suzuki–Miyaura coupling of various aryl iodides and bromides with different aryl boronic acids, yielding good to excellent product yields (87–95%) with TON of 86.86–94.84 and TOF of 1.996–3.161 min−1. One of the advantages of this catalyst is that it can be recycled at least three times for Mizoroki–Heck coupling reactions with only a marginal loss

  在这项研究中，我们成功地使用由Pd(OAc) 2和[C 18 –DABCO–C 18 ]2Br（比例为1: 10 mol%）组成的新型催化体系进行各种类型的C-C偶联反应，包括 Mizoroki-Heck 和 Suzuki-Miyaura，在水基介质中。使用 TEM 对催化剂体系进行分析，结果显示存在稳定的钯纳米颗粒 (PdNP)，其尺寸小于 5 nm，并受到“Gemini”型 [C 18 –DABCO–C 18 ]2Br 表面活性剂的保护。X射线光电子能谱（XPS）用于测定Pd的氧化态。我们的优化研究表明，该催化体系在一系列芳基碘化物和芳基溴化物与不同烯烃和芳基硼酸的偶联方面非常有效。该反应在80-100℃下以K 2 CO 3为碱进行，获得了80-93%的高产率。所有反应的选择性都非常好，范围为92-100%，周转数（TON）为79.72-92.77，周转频率（TOF）为0.997-2.059