butyl 2-methyl-3-phenylacrylate

• 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: butyl 2-methyl-3-phenylacrylate
• 英文别名: Butyl 2-methyl-3-phenylprop-2-enoate
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: AXVRAMHXZJBLOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-甲基-3-苯基-2-丙烯-1-醇 、 正丁醇 在 manganese(IV) oxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 4-甲氧基-3-硝基三氟甲苯 作用下， 以91%的产率得到butyl 2-methyl-3-phenylacrylate
  参考文献：
  名称：

  N-Heterocyclic carbene-catalyzed oxidations

  摘要：

  N-Hererocyclic carbenes catalyze the oxidation of allylic and benzylic alcohols as well as saturated aldehydes to esters with manganese(IV) oxide in excellent yields. A variety of esters can be synthesized,, protected carboxylates. The oxidation proceeds Under mild conditions, with low loadings of including a simple triazolium salt pre-catalyst in the presence of base. Substrates containing potentially epimerizable triazolium salt pre-catalyst in the presence of base. Substrates containing potentially epimerizable centers are oxidized while preserving stereochemical integrity. The acyl triazolium intermediate generated under catalytic conditions can be employed as a chiral acylating agent in the desymmetrization of meso-diols.

  DOI：

  10.1016/j.tet.2008.10.033

文献信息

• Click amidations, esterifications and one–pot reactions catalyzed by Cu salts and multimetal–organic frameworks (M–MOFs)
  作者：Rossella Greco、Estefanía Tiburcio、Brenda Palomar-De Lucas、Jesús Ferrando-Soria、Donatella Armentano、Emilio Pardo、Antonio Leyva-Pérez

  DOI：10.1016/j.mcat.2022.112228

  日期：2022.4

  reagents or reaction conditions. Here we show a “spring–loaded”, 100% atom–efficient amidation and esterification protocol which consists in the ring opening of cyclopropenones with amines or alcohols. Some alkyl amines react spontaneously at room temperature in a variety of solvents and reaction conditions, including water at different pHs, while other alkyl amines, aromatic amines and alcohols react in

  酰胺和酯是自然界、工业和学术实验室中普遍存在的化学物质。因此，多年来已经开发出大量用于这些化合物的合成方法也就不足为奇了。然而，这些方法不是 100% 原子经济的，并且通常需要苛刻的试剂或反应条件。在这里，我们展示了一种“弹簧加载”、100% 原子效率的酰胺化和酯化方案，该方案包括环丙烯酮与胺或醇的开环。一些烷基胺在室温下在各种溶剂和反应条件下自发反应，包括不同 pH 值的水，而其他烷基胺、芳香胺和醇在催化量的简单 Cu 2+存在下反应盐或固体。模块化反应模式（烷基胺 >> 烷基醇 >> 酚 >> 芳香胺）能够在定义明确的催化多金属-有机框架（M-MOF，M= Cu、Ni、Pd）上设计正交和一锅反应，以轻松地将所得的肉桂酰胺和肉桂酸酯官能化为更复杂的分子。此处报道的酰胺化和酯化反应条件与铜催化的叠氮化物-炔烃环加成 (CuAAC) 非常相似，因此可以将这种快速、清洁和灵活的方案定义为点击反应。
• Heck Reaction over Pd-Loaded ETS-10 Molecular Sieve
  作者：Suresh Babasaheb Waghmode、Smita Girish Wagholikar、Subramanian Sivasanker

  DOI：10.1246/bcsj.76.1989

  日期：2003.10

  A palladium-loaded ETS-10 molecular sieve has been used as a catalyst in Heck reaction. The catalyst exhibits high activity and selectivity towards the carbon–carbon coupling of aryl halides with olefins, even at low concentrations of Pd (0.009 to 1.4 mol% with respect to the substrate). In the case of the coupling of ethyl acrylate with iodobenzene, 96% conversion of iodobenzene with greater than

  载有钯的 ETS-10 分子筛已被用作 Heck 反应的催化剂。该催化剂对芳基卤化物与烯烃的碳-碳偶联表现出高活性和选择性，即使在低浓度 Pd（相对于底物为 0.009 至 1.4 mol%）时也是如此。在丙烯酸​​乙酯与碘苯偶联的情况下，在 0.2 wt% 的 Pd 负载催化剂上，可以在 1 小时内获得 96% 的碘苯转化率，选择性大于 98%。该催化剂活化芳基溴和氯化物底物，并且似乎是非均相的。该反应已用不同的卤代烷、烯烃和碱进行了研究。
• 1,1′-Methylene-3,3′-bis[(N-(tert-butyl)imidazol-2-ylidene] and Its Effect in Palladium-Catalyzed C–C Coupling
  作者：Mohammad Joshaghani、Shirin Nadri、Ezzat Rafiee、Sirous Jamali

  DOI：10.1055/s-0034-1379954

  日期：——

  A catalytic system utilizing a chelate carbene ligand containing bulk tert-butyl groups is described for palladium-catalyzed Heck and Suzuki coupling reactions. The Heck reaction focused on the coupling of different aryl bromides with mono- and 1,1-disubstituted olefins while the Suzuki reaction involved the coupling of aryl bromides and phenylboronic acid to afford the corresponding biphenyls. The

  描述了一种使用包含本体叔丁基的螯合卡宾配体的催化系统，用于钯催化的 Heck 和 Suzuki 偶联反应。Heck 反应侧重于不同的芳基溴化物与单和 1,1-二取代烯烃的偶联，而 Suzuki 反应涉及芳基溴化物和苯基硼酸的偶联以提供相应的联苯。该催化剂体系在 Pd(OAc)2 含量低（0.025 mol% Pd）时表现良好。在所有单取代烯烃的情况下，都获得了反式构型的产物，而 1,1-二取代烯烃的 Heck 反应结果显示出有利于最终产物的高选择性。
• A New Mode of Operation of Pd-NHC Systems Studied in a Catalytic Mizoroki–Heck Reaction
  作者：Alexander V. Astakhov、Oleg V. Khazipov、Andrey Yu. Chernenko、Dmitry V. Pasyukov、Alexey S. Kashin、Evgeniy G. Gordeev、Victor N. Khrustalev、Victor M. Chernyshev、Valentine P. Ananikov

  DOI：10.1021/acs.organomet.7b00184

  日期：2017.5.22

  Metal complexes bearing N-heterocyclic carbene (NHC) ligands are typically considered the system of choice for homogeneous catalysis with well-defined molecular active species due to their stable metal ligand framework. A detailed study involving 19 different Pd-NHC complexes with imidazolium, benzimidazolium, and triazolium ligands has been carried out in the present work and revealed a new mode of operation of metal-NHC systems. The catalytic activity of the studied Pd-NHC systems is predominantly determined by the cleavage of the metal NHC bond, while the catalyst performance is strongly affected by the stabilization of in situ formed metal clusters. In the present study, the formation of Pd nanopartides was observed from a broad range of metal complexes with NHC ligands under standard Mizoroki-Heck reaction conditions. A mechanistic analysis revealed two different pathways to connect Pd-NHC complexes to "cocktail"-type catalysis: (i) reductive elimination from a Pd(II) intermediate and the release of NHC-containing byproducts and (ii) dissociation of NHC ligands from Pd intermediates. Metal-NHC systems are ubiquitously applied in modern organic synthesis and catalysis, while the new mode of operation revealed in the present study guides catalyst design and opens a variety of novel opportunities. As shown by experimental studies and theoretical calculations, metal dusters and nanopartides can be readily formed from M-NHC complexes after formation of new M-C or M-H bonds followed by C-NHC or H-NHC coupling. Thus, a combination of a classical molecular mode of operation and a novel cocktail-type mode of operation, described in the present study, may be anticipated as an intrinsic feature of M-NHC catalytic systems.
• Heck Reactions without Salt Formation: Aromatic Carboxylic Anhydrides as Arylating Agents
  作者：Massoud S. Stephan、Antonius J. J. M. Teunissen、Gerard K. M. Verzijl、Johannes G. de Vries

  DOI：10.1002/(sici)1521-3773(19980316)37:5<662::aid-anie662>3.0.co;2-0

  日期：1998.3.16

  Environmentally benign and economical production of arylated olefins can be achieved by a new variant of the Heck reaction in which no halogen salts are formed. The trick is the use of aromatic carboxylic anhydrides 1 as arylating agents. With halide-activated palladium chloride as catalyst, which requires no phosphane ligands, the olefins 2 can be prepared according to Equation (a) in good yields.