3-(4-ethylphenyl)acrylic acid methyl ester | 87087-37-4

• 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: 3-(4-ethylphenyl)acrylic acid methyl ester
• 英文别名: Methyl 3-(4-ethylphenyl)prop-2-enoate
• CAS: 87087-37-4
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: QIOWPRYONMOYMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-ethylphenyl)acrylic acid methyl ester 在 二异丁基氢化铝 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.5h， 生成 4-ethylcinnamaldehyde
  参考文献：
  名称：

  共轭α-取代的二烯酸的高度区域和对映选择性加氢。

  摘要：

  使用Trifer-Rh配合物首次实现了对共轭α-取代二烯酸的高度区域和对映选择性加氢，为合成手性α-取代的γ，δ-不饱和酸提供了一种简单的方法。DFT计算表明，形成N + H–O氢键相互作用可稳定过渡态，并且4,5-双键与Rh（III）中心的配位将促进还原消除过程。该氢化提供了沙比特利前体的克级合成。

  DOI：

  10.1021/acs.orglett.0c00915
• 作为产物：
  描述：

  膦酰基乙酸甲酯二乙酯 、 4-乙基苯甲醛 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以97%的产率得到3-(4-ethylphenyl)acrylic acid methyl ester
  参考文献：
  名称：

  共轭α-取代的二烯酸的高度区域和对映选择性加氢。

  摘要：

  使用Trifer-Rh配合物首次实现了对共轭α-取代二烯酸的高度区域和对映选择性加氢，为合成手性α-取代的γ，δ-不饱和酸提供了一种简单的方法。DFT计算表明，形成N + H–O氢键相互作用可稳定过渡态，并且4,5-双键与Rh（III）中心的配位将促进还原消除过程。该氢化提供了沙比特利前体的克级合成。

  DOI：

  10.1021/acs.orglett.0c00915

文献信息

• Pd-Catalyzed desulfitative arylation of olefins by <i>N</i>-methoxysulfonamide
  作者：Subhadra Ojha、Niranjan Panda

  DOI：10.1039/d1ob02360h

  日期：——

  A novel Pd-catalyzed protocol for the desulfitative Heck-type reaction of N-methoxy aryl sulfonamides with alkenes was reported. The cross-coupling reaction was performed successfully with a variety of olefins to obtain aryl alkenes. Different substituents on the aromatic ring of N-methoxysulfonamides were also found to be compatible with the reaction conditions. Expectedly, the reaction proceeds through

  报道了一种用于N-甲氧基芳基磺酰胺与烯烃的脱硫 Heck 型反应的新型 Pd 催化方案。与多种烯烃成功地进行了交叉偶联反应，得到了芳基烯烃。N-甲氧基磺酰胺芳环上的不同取代基也被发现与反应条件相容。预期，该反应通过 CuCl 2促进氮自由基的产生和随后在热条件下脱磺酰化以提供用于 Pd 催化的偶联反应的芳基自由基进行。N-甲氧基磺酰胺被进一步开发用于在CuCl 2存在下合成对称联芳基化合物。
• Imidazolyl-Functionalized Ordered Mesoporous Polymer from Nanocasting as an Effective Support for Highly Dispersed Palladium Nanoparticles in the Heck Reaction
  作者：Babak Karimi、Mohammad Reza Marefat、Maliheh Hasannia、Pari Fadavi Akhavan、Fariborz Mansouri、Zahra Artelli、Fariba Mohammadi、Hojatollah Vali

  DOI：10.1002/cctc.201600630

  日期：2016.8.8

  FTIR spectroscopy. The material, which benefits from the use of entrapped ionic liquid in the prepared polymer matrix in combination with its ordered mesoporous structure, is an excellent environment for the stabilization of highly dispersed Pd nanoparticles to result in a recyclable catalyst system with a significant activity in the Heck coupling reaction of aryl halides. The presence of well‐distributed

  新型的咪唑基官能化的有序介孔交联聚合物是通过将离子液体3-苄基-1-乙烯基-1 H-咪唑鎓溴化物与二乙烯基苯作为交联剂，偶氮二异丁腈在自由基存在下共聚而制备的硅烷化的SBA-15作为硬模板。该材料的特征在于N 2。吸附-解吸分析，TEM，热重分析，元素分析和FTIR光谱。该材料得益于在制备的聚合物基质中使用截留的离子液体及其有序的介孔结构，是稳定高分散Pd纳米颗粒以形成可循环使用的催化剂体系的极佳环境，该体系具有良好的催化活性。芳基卤化物的Heck偶联反应。聚合物骨架中咪唑官能团的分布均匀可能是导致Pd纳米粒子在整个介孔结构中相对均匀且接近原子级分布的原因，并防止了反应过程中Pd的团聚，从而导致了高耐久性，高稳定性，以及良好的催化剂循环特性。
• Synthesis of 1,3,4,5-Tetrahydro-2-benzoxepin Derivatives as Conformationally Restricted Analogues of cyclamenaldehyde-type compounds and as intermediates for highly odour-active homologues
  作者：Georges Skouroumounis、B�at Winter

  DOI：10.1002/hlca.19960790418

  日期：1996.6.26

  Nine 1,3,4,5-tetrahydro-2-benzoxepin derivatives have been prepared as mimics of the folded (gauche) conformation of cyclamenaldehyde (1) and related compounds, but none of them showed the typical lily-of-the valley (muguet) odour activity. However, conversion of these substances to previously unknown analogues of 1 having a Me substituent on the aromatic ring in an ortho position to the side chain

  已制备了九种1,3,4,5-四氢-2-苯并二恶英衍生物，以模拟仙客来醛（1）及其相关化合物的折叠（gauche）构象，但它们均未显示出典型的铃兰（气味）。然而，将这些物质转化为先前未知的类似物1，该类似物在芳环的侧链的邻位具有Me取代基，从而产生了具有显着性能的新的芳香物质。结果表明，扩展的（抗）构象更有可能是在受体位点的“生物活性”构象。
• Spectroscopic and Computational Study of the Organocatalytic Umpolung of Bromocations: An Accelerated Stereoselective Dibromination Protocol**
  作者：Jeetendra Panda、Jigyansa Sahoo、Juhi Dutta、Himansu Sekhar Biswal、Gokarneswar Sahoo

  DOI：10.1002/chem.202300675

  日期：2023.8.10

  umpolung of cationic bromine from N-bromosuccinimide (NBS) using an amine organocatalyst is reported. The intermediate reagents and their reactivity have well been characterised by spectroscopic and computational methods. Strategic structural change in the NBS molecule can cause sufficient polarity reversal to accelerate the dibromination reaction needing both “Br” synthons. This has further been utilised

  报道了一种新开发的使用胺有机催化剂从N-溴代琥珀酰亚胺 (NBS) 中原位还原阳离子溴的方法。中间体试剂及其反应性已通过光谱和计算方法得到了很好的表征。NBS 分子的战略结构变化可以引起足够的极性反转，以加速需要两个“Br”合成子的二溴化反应。这已进一步用于具有广泛底物范围的烯烃的加速二溴化反应。
• Structure-activity relationships in 1,4-benzodioxan-related compounds. 4. Effect of aryl and alkyl substituents at position 3 on .alpha.-adrenoreceptor blocking activity
  作者：Wilma Quaglia、Maria Pigini、Seyed K. Tayebati、Alessandro Piergentili、Mario Giannella、Gabriella Marucci、Carlo Melchiorre

  DOI：10.1021/jm00063a002

  日期：1993.5

  The observation that the insertion of a phenyl ring at position 3 of WB 4101 (1) afforded a potent and selective alpha1-adrenoreceptor antagonist, phendioxan (2), prompted us to further investigate that position of the 2,3-dihydro-1,4-benzodioxin moiety. Thus the 3-phenyl of 2 was replaced by methyl, isopropyl, cyclohexyl, or para-substituted phenyl groups either in a cis or a trans relationships affording compounds 3-17 and 58. The structure of these new derivatives was assigned on the basis of the coupling constant of hydrogens at positions 2 and 3 and confirmed by a crystallographic study. The blocking activity and relative selectivity of 3-17 on alpha1- and alpha2-adrenoreceptors were evaluated in the isolated rat vas deferens. The results were compared with those obtained for 1 and 2. All the compounds, with the exception of isopropyl and cyclohexyl derivatives 5-8, were effective al-adrenoreceptor antagonists with a significant alpha1/alpha2-selectivity. The lipophilic and/or electronic character of para substituents of the 3-phenyl ring does not alter markedly the affinity toward alpha1-adrenoreceptors. However, the 3-p-tolyl derivative 10 was slightly more potent and even more selective than 2.