methyl (E)-3-(4-(((trifluoromethyl)sulfonyl)oxy)phenyl)acrylate | 137927-71-0

• 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 (E)-3-(4-(((trifluoromethyl)sulfonyl)oxy)phenyl)acrylate
• 英文别名: methyl (E)-3-[4-(trifluoromethylsulfonyloxy)phenyl]prop-2-enoate
• CAS: 137927-71-0
• 化学式: C₁₁H₉F₃O₅S
• 分子量: 310.251
• InChiKey: VJNZLRQXULXORM-QPJJXVBHSA-N

物化性质

• 沸点：
  371.3±42.0 °C(Predicted)
• 密度：
  1.464±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-(4-(((trifluoromethyl)sulfonyl)oxy)phenyl)acrylate 在 C₉₄H₁₃₄O₄P₂Pd₂ 、 cesium fluoride 作用下， 以 甲苯 为溶剂， 反应 14.0h， 以92%的产率得到3-(4'-氟苯基)-丙烯酸甲酯
  参考文献：
  名称：

  An Improved Catalyst System for the Pd-Catalyzed Fluorination of (Hetero)Aryl Triflates

  摘要：

  The stable Pd(0) species [(1,5-cyclooctadiene)(L.Pd)(2)] (L = AdBrettPhos) has been prepared and successfully evaluated as a precatalyst for the fluorination of aryl triflates derived from biologically active and heteroaryl phenols, challenging substrates for our previously reported catalyst system. Additionally, this precatalyst activates at room temperature under neutral conditions, generates 1,5-cyclooctadiene as the only byproduct, and leads to overall cleaner reaction profiles.

  DOI：

  10.1021/ol402859k
• 作为产物：
  描述：

  三氟甲磺酸酐 、 methyl 4-hydroxycinnamate 生成 methyl (E)-3-(4-(((trifluoromethyl)sulfonyl)oxy)phenyl)acrylate
  参考文献：
  名称：

  An Improved Catalyst System for the Pd-Catalyzed Fluorination of (Hetero)Aryl Triflates

  摘要：

  The stable Pd(0) species [(1,5-cyclooctadiene)(L.Pd)(2)] (L = AdBrettPhos) has been prepared and successfully evaluated as a precatalyst for the fluorination of aryl triflates derived from biologically active and heteroaryl phenols, challenging substrates for our previously reported catalyst system. Additionally, this precatalyst activates at room temperature under neutral conditions, generates 1,5-cyclooctadiene as the only byproduct, and leads to overall cleaner reaction profiles.

  DOI：

  10.1021/ol402859k

文献信息

• Olefin Metathesis, <i>p</i> ‐Cresol, and the Second Generation Grubbs Catalyst: Fitting the Pieces
  作者：Marthinus R. Swart、Linette Twigge、Elizabeth Erasmus、Charlene Marais、Barend C. B. Bezuidenhoudt

  DOI：10.1002/ejic.202100078

  日期：2021.5.14

  generation catalyst (GII) allows the cross‐metathesis of acrylates with prop‐1‐en‐1‐ylbenzenes under conditions that only give the prop‐1‐en‐1‐ylbenzene self‐metathesis product in the absence of cresol. NMR and IR spectroscopy, MALDI‐TOF MS and XPS supported the formation of a ruthenium benzylidene with hydrogen bonds between p‐cresol and the chloride ligands of GII. XPS furthermore confirmed p‐cresol

  对苯甲酚作为Grubbs第二代催化剂（GII）的添加剂，可以在只有丙-1-烯-1-基苯自我复分解产物的条件下，将丙烯酸与丙-1-烯-1-基苯进行交叉复分解在没有甲酚的情况下。NMR和IR光谱学，MALDI-TOF MS和XPS支持了在对甲酚和GII的氯化物配体之间具有氢键的钌亚苄基的形成。XPS还证实了对甲酚会增加GII Ru 3d 5/2，3d 3 / 2，3p 3/2和3p 1/2光电子线的结合能，而11 H NMR光谱表明卡宾碳和氢被保护。因此推测，对甲酚可以通过减少金属中心的电子密度和增加卡宾的电子密度，使缺电子化合物与钌亚苄基之间的相互作用更加轻松。
• Palladium-catalyzed triethylammonium formate reduction of aryl triflates. A selective method for the deoxygenation of phenols
  作者：Sandro Cacchi、Pier Giuseppe Ciattini、Enrico Morera、Giorgio Ortar

  DOI：10.1016/s0040-4039(00)85262-4

  日期：1986.1

  Phenols can be selectively deoxygenated by reduction of the corresponding aryl triflates with triethylammonium formate in the presence of a homogeneous palladium catalyst.

  在均相钯催化剂的存在下，通过用甲酸三乙铵还原相应的芳基三氟甲磺酸酯，可以对苯酚进行选择性脱氧。
• Nickel(0)-Catalyzed Reduction of Aryl Triflates with Zinc Powder and Methanol
  作者：Ken Sasaki、Mutsuji Sakai、Yasumasa Sakakibara、Kentaro Takagi

  DOI：10.1246/cl.1991.2017

  日期：1991.11

  Deoxygenative reduction of aryl Inflates was attained by using nickel(0)-dppp/PPh3 catalyst with zinc powder and methanol as a hydrogen donor.

  采用镍(0)-dppp/PPh3催化剂，锌粉和甲醇为氢供体，实现芳基Inflates的脱氧还原。
• The Quest for the Ideal Base: Rational Design of a Nickel Precatalyst Enables Mild, Homogeneous C–N Cross-Coupling
  作者：Richard Y. Liu、Joseph M. Dennis、Stephen L. Buchwald

  DOI：10.1021/jacs.0c00286

  日期：2020.3.4

  Palladium-catalyzed amination reactions using soluble organic bases have provided a solution to the many issues associated with heterogeneous reaction conditions. Still, homogeneous C-N cross-coupling approaches cannot yet employ bases as weak and economical as trialkylamines. Furthermore, organic base-mediated methods have not been developed for Ni(0/II) catalysis, despite some advantages of such systems

  使用可溶性有机碱的钯催化胺化反应为与多相反应条件相关的许多问题提供了解决方案。尽管如此，均相 CN 交叉偶联方法尚不能使用与三烷基胺一样弱且经济的碱。此外，尽管有机碱介导的方法与类似的 Pd 基催化剂相比具有一些优势，但尚未开发出用于 Ni(0/II) 催化的有机碱介导方法。我们设计了一种新的空气稳定且易于制备的 Ni(II) 预催化剂，其带有缺电子的双齿膦配体，能够使用三乙胺 (TEA) 作为碱使芳基三氟甲磺酸酯与芳基胺交叉偶联。该方法可以容忍空间拥挤的偶联伙伴，以及带有碱和亲核试剂敏感官能团的偶联伙伴。借助密度泛函理论 (DFT) 计算，我们确定缺电子辅助配体降低了 Ni 键合胺的 pKa 和从所得 Ni(II)-酰胺络合物还原消除的障碍。此外，我们确定，由于空间因素，排除 Ni 催化剂和碱之间的路易斯酸碱络合对于避免催化剂抑制很重要。
• CACCHI S.; CIATTINI P. G.; MORERA E.; ORTAR G., TETRAHEDRON LETT., 27,(1986) N 45, 5541-5544
  作者：CACCHI S.、 CIATTINI P. G.、 MORERA E.、 ORTAR G.

  DOI：——

  日期：——