methyl 3-(4-anisyl)-2-methylacrylate | 30780-60-0

• 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: methyl 3-(4-anisyl)-2-methylacrylate
• 英文别名: methyl α-methyl-p-methoxycinnamate；methyl 3-p-methoxyphenyl-2-methylpropenoate；methyl 3-(4-methoxyphenyl)-2-methylprop-2-enoate
• CAS: 30780-60-0
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: SCVOEXDTUOOUNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  4
• 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 3-(4-anisyl)-2-methylacrylate 以 四氢呋喃 为溶剂， 反应 11.0h， 生成 methyl (1R,3S)-3-(4-methoxyphenyl)-1,2,2-trimethylcyclopropane-1-carboxylate
  参考文献：
  名称：

  Photoinduced Electron Transfer Reaction of Pyrazoline Derivatives. Formation of Rearrangement Product

  摘要：

  The initial process of photoinduced electron transfer (PET) between electron deficient sensitizers and r-3-(methoxycarbonyl)-t-4-(para-substituted-phenyl)-3,5,5-trimethyl-1-pyrazolines 1 was investigated. Fluorescence quenching rate constants of the sensitizers by 1 and PET decomposition quantum yields of 1 reflect that the stability of the generated radical cations of 1 and the back-electron transfer play important roles in the reactivity. The generated radical cations of 1 followed by nitrogen elimination gave cyclopropane derivatives 2 and/or aryl migrated olefins 3. Product distributions between the cyclopropanes 2 and the olefins 3 depend on the para-substituent of the phenyl ring of 1. Semiempirical MO calculations (AM1) of the radical cations of 1 suggest the location of the spin and the charge governing the product distribution.

  DOI：

  10.1021/jo00130a030
• 作为产物：
  描述：

  methyl 2-[hydroxy(4-methoxyphenyl)methyl]prop-2-enoate 在 copper(II) choride dihydrate 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 methyl 3-(4-anisyl)-2-methylacrylate
  参考文献：
  名称：

  α-烷基 α,β-不饱和酯中的对映和非对映选择性硼共轭加成

  摘要：

  我们在无碱条件下开发了一种铜催化的对映选择性和非对映选择性硼共轭加成到 α-烷基 α,β-不饱和酯中。该方法显示出出色的对映选择性 (87–99% ee) 和中等至良好的转化率 (51–99%)，尽管具有中等的非对映选择性 (1 : 1–17 : 1 dr)。证明了该协议的综合效用。

  DOI：

  10.1039/d2ob01928k

文献信息

• Tetraphosphine/palladium-catalyzed Heck reactions of aryl halides with disubstituted alkenes
  作者：Isabelle Kondolff、Henri Doucet、Maurice Santelli

  DOI：10.1016/j.tetlet.2003.09.092

  日期：2003.11

  cyclopentane/[PdCl(C3H5)]2 efficiently catalyses the Heck reaction of disubstituted alkenes such as methyl crotonate, ethyl cinnamate, methyl methacrylate or α-methylstyrene with a variety of aryl halides. In the presence of 1,2-disubstituted alkenes the stereoselectivities of the reactions strongly depend on the substituents of the alkenes. Selectivities up to 97% in favor of E-isomers can be obtained

  顺式，顺式，顺式-1,2,3,4-四（二苯基膦甲基）环戊烷/ [PdCl（C 3 H 5）] 2有效催化巴豆酸甲酯，肉桂酸乙酯，甲基丙烯酸甲酯或α等二取代烯烃的Heck反应-甲基苯乙烯与各种芳基卤化物。在1，2-二取代的烯烃的存在下，反应的立体选择性强烈取决于烯烃的取代基。添加到巴豆酸甲酯中可以得到高达97％的选择性，有利于E-异构体。用1，1-二取代的烯烃获得甲基丙烯酸甲酯或α-甲基苯乙烯的产物混合物。
• Iron catalysis for the synthesis of ligands: Exploring the products of hydrophosphination as ligands in cross-coupling
  作者：Maialen Espinal-Viguri、Mary F. Mahon、Simon N.G. Tyler、Ruth L. Webster

  DOI：10.1016/j.tet.2016.11.058

  日期：2017.1

  Catalytic hydrophosphination is a useful technique for the synthesis of phosphines, however, the phosphine products have been little exploited as ligands in catalysis. We have selected three phosphines prepared by iron catalyzed hydrophosphination and used them as ligands in a series of cross-coupling reactions: Heck, Suzuki-Miyaura and Buchwald-Hartwig. Rather than limit the chemistry to simple cross-coupling

  催化氢磷酸化是合成膦的有用技术，但是，膦产物几乎没有被用作催化中的配体。我们选择了铁催化氢磷酸化制备的三种膦，并将它们用作一系列交叉偶联反应的配体：Heck，Suzuki-Miyaura和Buchwald-Hartwig。与其将化学反应局限于几乎可以保证在这些转化中表现良好的简单交叉偶联配偶体，还探索了从电子和/或立体角度来看具有挑战性的工业相关底物，以及包含多个杂原子的底物，以实现以下目的：测量这些膦配体的真正潜力。
• Palladium catalyst immobilized on functionalized microporous organic polymers for C–C coupling reactions
  作者：Wei Xu、Cijie Liu、Dexuan Xiang、Qionglin Luo、You Shu、Hongwei Lin、Yangjian Hu、Zaixing Zhang、Yuejun Ouyang

  DOI：10.1039/c9ra07303e

  日期：——

  density. Moreover, the immobilized catalyst also had advantages, such as readily available raw materials, chemical and thermal stability, and low synthetic cost. The Pd catalyst is an effective heterogeneous catalyst for carbon–carbon (C–C) coupling reactions, such as the Heck reaction and Suzuki–Miyaura reaction, affording good to high yields. In these reactions, the catalyst was easily recovered and reused

  以苯和1,10-菲咯啉为原料，分别通过Scholl偶联反应和Friedel-Crafts反应制备了两种微孔有机聚合物固定钯（MOP-Pd）催化剂。通过FT-IR、TGA、N 2吸附、SEM、TEM、ICP-AES和XPS对催化剂的结构和组成进行了表征。MOP-Pd 催化剂被发现具有高比表面积、大孔体积和低骨骼密度。此外，固定化催化剂还具有原料易得、化学和热稳定性好、合成成本低等优点。Pd催化剂是一种有效的多相催化剂，适用于碳-碳（C-C）偶联反应，例如Heck反应和Suzuki-Miyaura反应，具有良好的高产率。在这些反应中，催化剂很容易回收并重复使用五次，而没有明显的活性损失。
• Palladium Immobilized on 2,2′-Dipyridyl-Based Hypercrosslinked Polymers as a Heterogeneous Catalyst for Suzuki–Miyaura Reaction and Heck Reaction
  作者：Cijie Liu、Wei Xu、Dexuan Xiang、Qionglin Luo、Shunqin Zeng、Lijuan Zheng、Yujie Tan、Yuejun Ouyang、Hongwei Lin

  DOI：10.1007/s10562-020-03165-4

  日期：2020.9

  to characterize the structure and composition of the heterogeneous catalysts. The result indicates that HCPs-bipy-Pd possess high specific surface areas, large microporous volume, thermal stability, and highly dispersion of palladium species. HCPs-bipy-Pd can be applied in Suzuki–Miyaura reactions and Heck reactions as robust heterogeneous catalyst to afford high yield. The reusability test demonstrates

  摘要 2,2'-联吡啶通过Friedel-Crafts 反应和Scholl 偶联反应成功整合到超交联聚合物网络(HCPs-bipy) 的骨架中，PdCl 2 通过与吡啶基序配位锁定在该网络聚合物中。HCPs-bipy的制备具有成本低、条件温和、易分离、收率高等优点。采用 FT-IR、TGA、N 2 吸附、ICP、XPS、SEM、EDX 和 TEM 来表征多相催化剂的结构和组成。结果表明，HCPs-bipy-Pd 具有高比表面积、大微孔体积、热稳定性和钯物种的高度分散性。HCPs-bipy-Pd 可作为稳健的多相催化剂应用于 Suzuki-Miyaura 反应和 Heck 反应，以提供高产率。可重复使用性测试表明，HCPs-bipy-Pd 可以回收并重复使用至少 5 次而不会失去催化活性。图形摘要
• Pd(diimine)Cl2 embedded heterometallic compounds with porous structures as efficient heterogeneous catalysts
  作者：Sheng-Li Huang、Ai-Quan Jia、Guo-Xin Jin

  DOI：10.1039/c3cc38714c

  日期：——

  Four porous heterometallic coordination polymers were synthesized via a metalloligand strategy. All of them contain the [Pd(diimine)Cl2] moiety, which has good catalytic activity, and present remarkable versatility for catalysing Suzuki–Miyaura and Heck reactions.

  通过金属配体策略合成了四种多孔异金属配位聚合物。它们均包含具有良好催化活性的[Pd(diimine)Cl2]基团，并在催化铃木–宫浦反应和赫克反应方面展现出显著的多样性。