(E)-3-(3,5-bistrifluoromethylphenyl)acrylic acid butyl ester

• 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: (E)-3-(3,5-bistrifluoromethylphenyl)acrylic acid butyl ester
• 英文别名: butyl (2E)-3-(3,5-bis(trifluoromethyl)phenyl)acrylate；butyl (E)-3-(3,5-bis(trifluoromethyl)phenyl)acrylate；3,5-bis(trifluoromethyl)cinnamic acid n-butyl ester；butyl (E)-3-[3,5-bis(trifluoromethyl)phenyl]prop-2-enoate
• 化学式: C₁₅H₁₄F₆O₂
• 分子量: 340.265
• InChiKey: JWURBBVJKIEUGQ-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  丙烯酸丁酯 、 3,5-双三氟甲基溴苯 在 chloro-[2-(9-phenyl-1,10-phenanthrolin-2-yl)phenyl]palladium 、 sodium acetate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 48.0h， 以89%的产率得到(E)-3-(3,5-bistrifluoromethylphenyl)acrylic acid butyl ester
  参考文献：
  名称：

  钯NNC-Pincer配合物作为Mizoroki-Heck反应的有效催化剂前体

  摘要：

  芳族卤化物（碘化物，溴化物或氯化物）与活性烯烃在钯NNC-钳夹配合物（ppb）至ppm负载量下的Mizoroki-Heck反应得到了相应的内部烯烃，收率很好。总周转次数和周转频率分别达到8.70×10 8和1.21×10 7 h -1（3.36×10 3 s -1）。该催化剂用于UV-B防晒剂辛诺酸酯（2-乙基己基4-甲氧基肉桂酸酯）的10克级合成。反应速率分析，反应混合物的透射电子显微镜检查和中毒试验表明，单体钯物质是催化循环中的催化活性物质。

  DOI：

  10.1002/adsc.201800099

文献信息

• Heck-type coupling vs. conjugate addition in phosphine–rhodium catalyzed reactions of aryl boronic acids with α,β-unsaturated carbonyl compounds: a systematic investigation
  作者：Gang Zou、Jianping Guo、Zhiyong Wang、Wen Huang、Jie Tang

  DOI：10.1039/b615473e

  日期：——

  Heck-type coupling and conjugate addition by synergistically tuning the supporting ligand, the boronic acid to olefin ratio and other reaction conditions. Conjugate addition with selectivity >99% and Heck-type coupling with selectivity of up to 100%, 98% and 84% for acrylates, acrylamides and methyl vinyl ketone, respectively, could be achieved in the rhodium-catalyzed reactions of aryl boronic acids

  在甲苯-H（2）O双相系统中，已系统研究了膦-铑催化的芳基硼酸与α，β-不饱和羰基的反应中的Heck型偶联和共轭加成之间的竞争。除了铑的内在性质和羰基的烯醇化之外，发现铑上的膦支持配体，芳基硼酸与α，β-不饱和羰基的比例以及水相的pH值均显着影响竞争。因此，已经通过协同调节载体配体，硼酸与烯烃的比例和其他反应条件，开发了用于Heck型偶联和共轭物加成的高选择性铑基催化剂体系。共轭添加的选择性> 99％，Heck型偶联的选择性高达100％，
• Lipids as versatile solvents for chemical synthesis
  作者：Ashot Gevorgyan、Kathrin H. Hopmann、Annette Bayer

  DOI：10.1039/d1gc02311j

  日期：——

  Development of safe, renewable, cheap and versatile solvents is a longstanding challenge in chemistry. We show here that vegetable oils and related systems can become prominent solvents for organic synthesis. Suzuki–Miyaura, Hiyama, Stille, Sonogashira and Heck cross-couplings proceed with quantitative yields in a range of vegetable oils, fish oil, butter and waxes used as solvents. Appropriate methodologies

  开发安全、可再生、廉价且用途广泛的溶剂是化学领域的一项长期挑战。我们在这里展示了植物油和相关系统可以成为有机合成的主要溶剂。Suzuki–Miyaura、Hiyama、Stille、Sonogashira 和 Heck 交叉偶联在一系列用作溶剂的植物油、鱼油、黄油和蜡中进行定量产率。介绍了适用于植物油和相关脂质的高通量筛选和可持续分离技术的适当方法。
• Method for producing palladium complex compound
  申请人：Central Glass Company, Limited

  公开号：US20020111482A1

  公开（公告）日：2002-08-15

  An aromatic compound represented by the general formula Ar 1 X is reacted with a palladium compound and a phosphine derivative, in the presence of a first basic substance, thereby producing a palladium-complex compound represented by the general formula Ar 1 —PdL 2 X. This palladium-complex compound is reacted with a benzoic acid represented by the general formula Ar 2 —COOH, in the presence of a second basic substance, thereby producing another palladium-complex compound represented by the following general formula. 1 The above palladium-complex compounds are useful as catalysts and can be produced easily by the above reactions. In the above general formulas, Ar 1 is an aryl group; and X is a halogen that is fluorine, chlorine, bromine or iodine, trifluoromethanesulfonate group, an alkylsulfonate group having a carbon atom number of 1-4, or a substituted or unsubstituted arylsulfonate group; each L is independently a phosphine ligand; and Ar 2 is an aryl group.

  一种由通式Ar1X表示的芳香化合物，与钯化合物和膦衍生物在第一碱性物质的存在下反应，从而产生由通式Ar1-PdL2X表示的钯络合物化合物。这种钯络合物化合物与由通式Ar2-COOH表示的苯甲酸在第二碱性物质的存在下反应，从而产生另一种由以下通式表示的钯络合物化合物。上述钯络合物化合物是有用的催化剂，并且可以通过上述反应轻松制备。在上述通式中，Ar1是芳基基团；X是氟、氯、溴或碘、三氟甲磺酸基团、具有1-4个碳原子数的烷基磺酸盐基团，或取代或未取代的芳基磺酸盐基团；每个L都是独立的膦配体；而Ar2是芳基基团。
• Triaryl phosphine-functionalized N-heterocyclic carbene ligands for Heck reaction
  作者：Ai-E Wang、Jian-Hua Xie、Li-Xin Wang、Qi-Lin Zhou

  DOI：10.1016/j.tet.2004.10.049

  日期：2005.1

  A new type of triaryl phosphine-functionalized imidazolium salts 6 were prepared. Their palladium complexes, generated in situ, were successfully applied in the palladium-catalyzed Heck reaction. Using 1 mol% of Pd(dba)(2) and 10 mol% 6c in the presence of 2 equiv of K2CO3 in DMAc has proven to be highly efficient for the coupling of a wide array of aryl bromides and iodides with acrylates in excellent yield. The coupling of 4-bromotoluene with various styrene derivatives catalyzed by Pd/6c complex also gave good results. (C) 2004 Elsevier Ltd. All rights reserved.
• Efficient Heck Vinylation of Aryl Halides Catalyzed by a New Air-Stable Palladium−Tetraphosphine Complex
  作者：Marie Feuerstein、Henri Doucet、Maurice Santelli

  DOI：10.1021/jo015645b

  日期：2001.8.1