ethyl 2-trifluoromethylcinnamate | 50620-98-9

• 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: ethyl 2-trifluoromethylcinnamate
• 英文别名: ethyl 3-[2-(trifluoromethyl)phenyl]acrylate；2-Trifluoromethylcinnamic acid ethyl ester；ethyl 3-[2-(trifluoromethyl)phenyl]prop-2-enoate
• CAS: 50620-98-9
• 化学式: C₁₂H₁₁F₃O₂
• 分子量: 244.213
• InChiKey: SMBXVOLINKNRSR-UHFFFAOYSA-N

物化性质

• 沸点：
  272.8±35.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 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：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-trifluoromethylcinnamate 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 3.5h， 生成
  参考文献：
  名称：

  Origin of Stereocontrol in Guanidine-Bisurea Bifunctional Organocatalyst That Promotes α-Hydroxylation of Tetralone-Derived β-Ketoesters: Asymmetric Synthesis of β- and γ-Substituted Tetralone Derivatives via Organocatalytic Oxidative Kinetic Resolution

  摘要：

  The mechanism of asymmetric a-hydroxylation of tetralone-derived beta-ketoesters with guanidine-bisurea bifunctional organocatalyst in the presence of cumene hydroperoxide (CHP) was examined by means of DFT calculations to understand the origin of the stereocontrol in the reaction. The identified transition-state model was utilized to design an enantioselective synthesis of beta- or gamma-substituted tetralones by catalytic oxidative kinetic resolution reaction of tetralone-derived beta-ketoesters. This kinetic resolution reaction proceeded with high selectivity, and selectivity factors (s value) of up to 99 were obtained. The potential utility of this oxidative kinetic resolution method for synthesis of natural products was confirmed by applying it to achieve an enantioselective synthesis of (+)-linoxepin (13) from beta-substituted tetralone rac-7 in only six steps.

  DOI：

  10.1021/ja511149y
• 作为产物：
  描述：

  2-(三氟甲基)苯丙烯酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 ethyl 2-trifluoromethylcinnamate
  参考文献：
  名称：

  肉桂酸酯及其衍生物作为潜在的植物保护用抗真菌剂的生物活性和构效关系。

  摘要：

  合成了一系列肉桂酸酯及其衍生物，并通过菌丝体生长速率法评估了其对四种植物病原真菌的体外抗真菌活性。还得出了构效关系。几乎所有化合物在0.5 mM时对每种真菌均表现出一定的抑制活性。八种化合物对真菌的平均活性较高，对真菌的平均EC50值为17.4-28.6μg/ mL，比商品杀真菌剂标准多菌灵甲基多菌灵对苯二氮芥或kresoxim-的活性高出商业杀菌剂多菌灵标准多菌灵。甲基对P. grisea和Valsa mali都有抗性。化合物C1和C2具有较高的活性，平均EC50值为17.4和18.5μg/ mL，具有开发新型植物抗真菌剂的巨大潜力。结构-活性关系分析表明，醇部分中苯环和烷基的取代方式均显着影响活性。苯环上的取代基与醇部分中的烷基之间的活性存在复杂的综合影响。因此，肉桂酸酯由于具有高活性，天然化合物或天然化合物骨架，结构简单，易于制备，成本低廉和环保等优点，在开发用于植物保护的新型抗真菌

  DOI：

  10.1371/journal.pone.0176189

文献信息

• Investigation on the Coordination Mode of IL-Supported Diols Used as Phosphine-Free Ligands for Palladium Catalyzed Heck Reaction
  作者：Yueqin Cai、Gonghua Song、Xiao Chen

  DOI：10.1002/cjoc.201300461

  日期：2013.10

  The coordination mode of IL‐supported diols used as phosphine‐free ligands for palladium catalyzed Heck reaction has been investigated by tuning their compositions. The difference in coordination of these IL‐supported diols with metal Pd in Heck reaction was related to the changes of the cation rings, leading to the different activities of Pd catalyst in the reaction. The experimental results indicated

  通过调节其组成，研究了IL支撑的二醇作为钯催化的Heck反应的无膦配体的配位模式。这些IL负载的二醇与金属Pd在Heck反应中的配位差异与阳离子环的变化有关，导致Pd催化剂在反应中的活性不同。实验结果表明，Pd催化剂的活性主要受阳离子环的π电子密度影响。与吡啶鎓和哌啶鎓阳离子相比，咪唑鎓阳离子显示出对金属Pd的最佳配位。同时，C-2氢和烷基侧链的长度也影响配位。
• Preparation of active and robust palladium nanoparticle catalysts stabilized by diamine-functionalized mesoporous polymers
  作者：Rong Xing、Yueming Liu、Haihong Wu、Xiaohong Li、Mingyuan He、Peng Wu

  DOI：10.1039/b815186e

  日期：——

  A two-step chemical modification process is designed for synthesizing novel diamine-functionalized mesopolymers, which combine the advantage of organic polymers and mesoporous materials, and serve as an efficient scaffold for supporting highly dispersed, catalytically active and robust Pd nanoparticles (NPs).

  设计了一种两步化学修饰过程，用于合成新型二胺功能化介孔聚合物，这些聚合物结合了有机聚合物和介孔材料的优点，作为高效的支架，以支持高度分散、催化活性强且稳定的钯纳米颗粒（NPs）。
• Application of Bidentate Oxazoline–Carbene Ligands with Planar and Central Chirality in Asymmetric β-Boration of α,β-Unsaturated Esters
  作者：Zonghong Niu、Jianqiang Chen、Zhen Chen、Manyuan Ma、Chun Song、Yudao Ma

  DOI：10.1021/jo5021135

  日期：2015.1.2

  oxazoline-substituted imidazolium salts based on [2.2]paracyclophane were synthesized and characterized. The new bidentate oxazoline–carbene precursor with planar and central chirality had significant advantage than the bicyclic 1,2,4-triazolium salt derived from [2.2]paracyclophane as a monodentate carbene ligand in Cu(I)-catalyzed asymmetric β-boration of α,β-unsaturated esters, giving the desired products

  合成并表征了一系列基于[2.2]对环环烷的新的恶唑啉取代的咪唑鎓盐。新型的具有平面和中心手性的二齿恶唑啉-卡宾前体比由[2.2]对环环烷作为单齿卡宾配体的双环1,2,4-三唑鎓盐在Cu（I）催化的α的不对称β-硼酸酯上具有明显的优势。 ，β-不饱和酯，以高对映选择性和产率得到所需产物。
• Isoxazole compounds useful for the prophylaxis or treatment of nervous
  申请人：Sankyo Company, Limited

  公开号：US06005116A1

  公开（公告）日：1999-12-21

  Isoxazole compounds having the following general formula: ##STR1## wherein R.sup.1 represents an optionally substituted aryl group or aromatic heterocyclic group; R.sup.2 represents a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkenyl group, an alkoxy group, a cyano group, a carboxyl group, an alkanoyl group, an alkoxycarbonyl group or an optionally substituted carbamoyl group; R.sup.3 represents an optionally substituted amino group or a saturated heterocyclic group; X represents an oxygen atom or a sulfur atom; and n is an integer of from 2 to 6. These compounds have excellent monoamine oxidase inhibitory activity and are useful as a therapeutic agent or a preventive agent against nervous diseases such as depression.

  具有以下一般式的异噁唑化合物：##STR1## 其中 R.sup.1 代表可选取代的芳基或芳香杂环基；R.sup.2 代表氢原子、卤原子、可选取代的烷基、烯基、炔基、环烷基、环烯基、烷氧基、氰基、羧基、酰基、烷氧羰基或可选取代的氨基甲酰基；R.sup.3 代表可选取代的氨基或饱和杂环基；X 代表氧原子或硫原子；n 为2到6的整数。这些化合物具有出色的单胺氧化酶抑制活性，并可用作治疗剂或预防神经疾病如抑郁症的药物。
• Regioselective Coupling of Different Conjugate Esters by Magnesium Metal Reduction: A Route to Unsymmetrical Adipic Acid Esters
  作者：Tianyuan Zhang、Jiawu Zhang、Akihiro Mori、Taku Morii、Keisuke Kuramochi、Hirofumi Maekawa

  DOI：10.1021/acs.joc.3c01982

  日期：2023.11.17

  unsymmetrical 3-aryladipic acid esters has been developed via magnesium-promoted reductive coupling of ethyl cinnamates with methyl acrylate. In the present methodology, 3-aryladipic acid derivatives were prepared with good functional group tolerance and a wide substrate scope under very mild reaction conditions in good yields. The application of this reaction to dienic acid esters led to the successful control

  通过镁促进肉桂酸乙酯与丙烯酸甲酯的还原偶联，开发了一种合成不对称 3-芳基己二酸酯的新策略。在本方法中，在非常温和的反应条件下以良好的收率制备了具有良好官能团耐受性和广泛底物范围的3-芳基己二酸衍生物。将该反应应用于二烯酸酯，成功控制了反应，得到了具有高区域选择性的5-芳基-辛-3-烯二酸酯。